100 Greatest Songs from 1940

The 1940s was a decade marked by significant global events, including World War II and the post-war period of recovery and reconstruction. Throughout this time, music played an important role in boosting morale, providing comfort and entertainment, and reflecting the social and cultural changes of the era. The 1940s saw the rise of popular music genres such as swing, jazz, and big band, as well as the emergence of iconic performers such as Bing Crosby, Frank Sinatra, and Billie Holiday. The 100 Greatest Popular Songs of the 1940s is a curated list of the most memorable and influential songs of the decade. The list includes classics such as “In The Mood” by Glenn Miller, “White Christmas” by Bing Crosby, and “Sentimental Journey” by Doris Day. These songs continue to be beloved by audiences today and are a testament to the enduring legacy of 1940s music. From wartime anthems to romantic ballads, the music of the 1940s reflects the spirit and emotions of a tumultuous and transformative decade in world history. This list serves as a tribute to the music that defined a generation and continues to captivate listeners with its timeless melodies and lyrics.

1. White Christmas – Bing Crosby

“White Christmas” is a classic Christmas song that was originally performed by Bing Crosby in 1942. It was written by Irving Berlin and has since become one of the most popular and enduring holiday songs of all time. The song’s nostalgic lyrics and Crosby’s smooth crooning make it a heartwarming reminder of the joy and warmth of the Christmas season. The song has been covered by numerous artists over the years, but Crosby’s version remains the most beloved and iconic. Its popularity has endured for nearly 80 years, and it continues to be a staple of holiday music playlists around the world.

2. The Christmas Song – Nat “King” Cole

“The Christmas Song” is a holiday classic originally recorded by Nat “King” Cole in 1946. The song was written by Mel Tormé and Bob Wells and is often referred to by its opening line, “Chestnuts roasting on an open fire.” Cole’s smooth, velvety voice perfectly captures the warmth and coziness of the holiday season, and the song’s beautiful melody and heartfelt lyrics have made it a beloved staple of Christmas music for decades. The song has been covered by countless artists over the years, but it is Cole’s timeless rendition that remains the definitive version, capturing the essence of the holiday season and bringing joy to listeners of all ages.

3. God Bless The Child – Billie Holiday

“God Bless the Child” is a jazz standard that was originally recorded by Billie Holiday in 1941. The song was written by Holiday and Arthur Herzog Jr. and is a powerful and poignant reflection on the importance of self-reliance and independence. Holiday’s emotive vocals, backed by a simple but powerful jazz arrangement, convey the pain and struggle of growing up in poverty and the strength and determination it takes to overcome adversity. The song’s message of resilience and perseverance has resonated with audiences for generations, and it remains one of Holiday’s most iconic and enduring recordings, a testament to her artistry and influence on American music.

4. Take The “A” Train – Duke Ellington

“Take the ‘A’ Train” is a jazz standard that was composed by Billy Strayhorn and made famous by Duke Ellington and his orchestra. The song was first recorded in 1941 and is named after the subway line that ran to Harlem, where Ellington and his band were based. The song’s infectious melody and upbeat swing rhythm perfectly capture the excitement and energy of New York City, and the tight arrangement and virtuosic solos showcase the incredible musicianship of Ellington and his ensemble. “Take the ‘A’ Train” has since become one of the most iconic jazz compositions of all time, a timeless testament to Ellington’s genius as a composer and bandleader.

5. Star Dust – Artie Shaw

“Stardust” is a classic jazz standard that was first recorded by Artie Shaw and his orchestra in 1940. The song was composed by Hoagy Carmichael with lyrics by Mitchell Parish, and its dreamy melody and poetic lyrics have made it a beloved favorite of jazz fans around the world. Shaw’s clarinet playing on the recording is a masterpiece of virtuosity and sensitivity, and the lush orchestral arrangement adds to the song’s romantic and ethereal quality. “Stardust” has been covered by countless artists over the years, but it is Shaw’s iconic version that remains the definitive interpretation of this timeless classic.

6. Swinging On A Star – Bing Crosby

“Swinging on a Star” is a classic song that was written by Jimmy Van Heusen and Johnny Burke for the 1944 film “Going My Way,” where it was performed by Bing Crosby. The song’s playful melody and clever lyrics describe the different animals that one could be if they’re not careful, encouraging listeners to make the most of their lives. Crosby’s laid-back, easygoing vocal style perfectly captures the song’s lighthearted spirit, and the upbeat swing arrangement adds to the fun and playful vibe of the song. “Swinging on a Star” has since become a beloved favorite of jazz and swing fans around the world.

7. You Always Hurt The One You Love – Mills Brothers

“You Always Hurt the One You Love” is a classic ballad that was first recorded by the Mills Brothers in 1944. The song was written by Allan Roberts and Doris Fisher and has since become a staple of the Great American Songbook. The Mills Brothers’ smooth vocal harmonies and understated arrangement perfectly capture the bittersweet emotions of the song, describing the paradoxical nature of love and heartbreak. The song’s timeless message has resonated with audiences for generations, and it has since been covered by numerous artists, but the Mills Brothers’ version remains the definitive recording, a testament to their incredible talent and influence on American music.

8. Boogie Woogie Bugle Boy – Andrews Sisters

“Boogie Woogie Bugle Boy” is a classic song that was first recorded by the Andrews Sisters in 1941. The song was written by Don Raye and Hughie Prince and features a swinging boogie-woogie beat and infectious harmonies. The Andrews Sisters’ energetic and playful vocals perfectly capture the song’s upbeat and fun vibe, and their tight harmonies and rhythmic precision showcase their incredible talent as vocalists. “Boogie Woogie Bugle Boy” has since become a beloved classic of the swing era, a testament to the Andrews Sisters’ influence on American music

9. Chattanooga Choo Choo – Glenn Miller (Tex Beneke & the Modernaires)

“Chattanooga Choo Choo” is a classic big band song that was first recorded by Glenn Miller and his orchestra in 1941, featuring Tex Beneke and the Modernaires on vocals. The song was written by Mack Gordon and Harry Warren and describes a train trip from New York City to Chattanooga, Tennessee. The song’s catchy melody and upbeat swing rhythm perfectly capture the excitement and energy of train travel, and Beneke and the Modernaires’ smooth vocal harmonies add to the song’s fun and lighthearted vibe. “Chattanooga Choo Choo” has since become a beloved favorite of the swing era, a testament to Miller’s genius as a bandleader and arranger.

10. Paper Doll – Mills Brothers

“Paper Doll” by the Mills Brothers is a classic song from the 1940s that tells the story of a man who falls in love with a paper doll and wishes she were real. The song’s simple, catchy melody and the Mills Brothers’ smooth vocal harmonies make it a memorable tune that has stood the test of time. The song’s lyrics, though somewhat whimsical, also convey a sense of longing and loneliness that many listeners can relate to.

11. Rudolph, The Red-Nosed Reindeer – Gene Autry

“Rudolph, The Red-Nosed Reindeer” by Gene Autry is a beloved Christmas classic that has been enjoyed by generations of listeners. The song tells the story of Rudolph, a reindeer with a bright red nose who is initially shunned by his fellow reindeer but ultimately becomes a hero when he leads Santa’s sleigh through a stormy night. Autry’s warm, twangy voice and the song’s upbeat melody make it a joyful and uplifting tune that captures the spirit of the holiday season. The song’s enduring popularity has made it a staple of Christmas playlists and celebrations around the world.

12. Sentimental Journey – Les Brown (Doris Day)

“Sentimental Journey” by Les Brown featuring Doris Day is a nostalgic song that evokes memories of home and loved ones during wartime. The song’s upbeat tempo and Doris Day’s clear, crisp vocals make it a joyful and uplifting tune that captures the optimism of returning home after a long journey. The song’s lyrics, written by Bud Green, Les Brown, and Ben Homer, express a longing for familiar sights and sounds, and Day’s heartfelt delivery adds to the song’s emotional resonance.

13. I’ll Be Seeing You – Bing Crosby / Tommy Dorsey (Frank Sinatra)

“I’ll Be Seeing You” is a timeless classic that has been covered by many great artists, including Bing Crosby, Tommy Dorsey, and Frank Sinatra. The song’s haunting melody and poignant lyrics make it a powerful ballad that captures the bittersweet feeling of longing for a loved one who is far away. Crosby’s smooth, mellifluous voice and Dorsey’s lush orchestration create a dreamy, nostalgic mood that perfectly complements the song’s wistful lyrics. Sinatra’s version, which is arguably the most famous, showcases his trademark phrasing and emotional depth, making it a standout rendition of an already unforgettable tune.

14. I’ll Never Smile Again – Tommy Dorsey (Frank Sinatra)

\

“I’ll Never Smile Again” by Tommy Dorsey featuring Frank Sinatra is a melancholy ballad that expresses the pain of lost love. The song’s slow tempo and Sinatra’s heartfelt delivery create a hauntingly beautiful melody that lingers long after the song has ended. The lyrics, written by Ruth Lowe, express the depths of sorrow and heartache that can come with a broken heart, and Sinatra’s performance captures the emotion of the song perfectly.

15. Riders In The Sky (A Cowboy Legend) – Vaughn Monroe / Peggy Lee

“Riders In The Sky (A Cowboy Legend)” is a classic Western song that has been covered by many artists, including Vaughn Monroe and Peggy Lee. The song tells the story of a cowboy who encounters the ghostly spirits of the “devil’s herd” as he rides across the open range. The song’s driving tempo and lively melody capture the excitement and danger of the cowboy lifestyle, while the haunting chorus creates a sense of foreboding and mystery. Monroe’s rich baritone voice and Lee’s sultry delivery add depth and texture to the song, making it a timeless classic of the Western genre.

16. Auld Lang Syne – Guy Lombardo

“Auld Lang Syne” is a traditional Scottish folk song that has become a beloved New Year’s Eve tradition around the world. Guy Lombardo’s version, featuring his orchestra and vocal group, is perhaps the most famous recording of the song. The song’s lilting melody and nostalgic lyrics express a sense of farewell to the past and hope for the future. Lombardo’s arrangement, which features his trademark “sweet” sound, creates a dreamy, romantic mood that perfectly captures the sentiment of the song.

17. That’s My Desire – Frankie Laine / Sammy Kaye

“That’s My Desire” is a classic love song that has been covered by many great artists, including Frankie Laine and Sammy Kaye. The song’s slow tempo and lush orchestration create a sensual, romantic atmosphere that perfectly complements the song’s lyrics, which express a deep longing for a lost love. Laine’s rich, powerful voice and Kaye’s smooth, jazzy arrangement make this version of the song a standout, showcasing the best of the romantic ballad genre. The song has become a standard of the American Songbook, and it remains a favorite of listeners who appreciate the timeless appeal of classic love songs.

18. Don’t Fence Me In – Bing Crosby & the Andrews Sisters / Roy Rogers / Gene Autry

“Don’t Fence Me In” is a classic Western song that has been covered by several artists, including Bing Crosby and the Andrews Sisters, Roy Rogers, and Gene Autry. The song’s upbeat tempo and catchy melody create a sense of freedom and adventure that perfectly captures the spirit of the American West. The lyrics, written by Cole Porter, express a longing for wide-open spaces and a life free from the constraints of civilization. Each artist brings their unique style and interpretation to the song, making each version a memorable tribute to the Western genre.

19. Jingle, Jangle, Jingle – Kay Kyser / Gene Autry

https://youtu.be/s0ofuXYkYi0
“Jingle, Jangle, Jingle” is a playful and infectious tune that has become a beloved classic of the Western genre. Kay Kyser’s version, featuring his big band and vocalist Harry Babbitt, was the first to popularize the song in 1942, but it was Gene Autry’s rendition that became the most famous. The song’s upbeat tempo, catchy melody, and lively chorus create a sense of fun and whimsy that perfectly capture the spirit of the Old West. The song’s playful lyrics, which describe the sound of a cowboy’s spurs and the jingle of his horse’s bridle, have become iconic, and the song remains a favorite of Western fans and music lovers alike.

20. Tuxedo Junction – Glenn Miller

“Tuxedo Junction” is a classic big band jazz instrumental that was made famous by Glenn Miller and his orchestra. The song’s catchy melody, lively horns, and swinging rhythm make it a joyous and infectious tune that is impossible not to dance to. The song’s title refers to a popular ballroom dance hall in Birmingham, Alabama, where many of the great big bands of the swing era played. Miller’s arrangement, which features the trombone section in the lead, is a masterclass in big band jazz, and the song remains a favorite of jazz fans and music lovers alike.

21. Nature Boy – Nat “King” Cole / Frank Sinatra / Sarah Vaughan

“Nature Boy” is a hauntingly beautiful ballad that has been covered by several great artists, including Nat “King” Cole, Frank Sinatra, and Sarah Vaughan. The song’s mystical lyrics, written by Eden Ahbez, describe a “strange enchanted boy” who wanders through nature and imparts wisdom to those he meets. The song’s slow tempo and lush orchestration create a dreamy, otherworldly atmosphere that perfectly complements the lyrics’ mystical quality. Each artist brings their unique style and interpretation to the song, making each version a memorable tribute to one of the most evocative and enigmatic ballads of the 20th century.

22. Brazil – Xavier Cugat / Jimmy Dorsey (Bob Eberly & Helen O’Connell)

“Brazil” is a lively Latin dance tune that was popularized by Xavier Cugat and his orchestra in the 1940s. The song’s infectious rhythm, exotic melody, and colorful instrumentation make it a joyous celebration of Brazilian culture and music. Cugat’s arrangement, which features his signature Latin rhythms and a lively brass section, perfectly captures the festive and sensual spirit of the song. Bob Eberly and Helen O’Connell’s version, backed by Jimmy Dorsey’s orchestra, adds a touch of American swing to the song, creating a unique blend of Latin and swing that is irresistible.

23. Green Eyes – Jimmy Dorsey (Bob Eberly & Helen O’Connell)

“Green Eyes” is a romantic ballad that was made famous by Jimmy Dorsey and his orchestra, featuring the vocal talents of Bob Eberly and Helen O’Connell. The song’s slow tempo, lush orchestration, and melancholy lyrics create a nostalgic and romantic atmosphere that perfectly captures the spirit of the 1940s. Eberly and O’Connell’s smooth and sultry vocals, combined with Dorsey’s elegant and emotive arrangements, make the song a timeless classic of the big band era. The song’s haunting melody and bittersweet lyrics have made it a favorite of lovers and romantics for generations.

24. Frenesi – Artie Shaw

“Frenesi” is a lively and infectious Latin jazz tune that was popularized by Artie Shaw and his orchestra in the 1940s. The song’s catchy melody, driving rhythm, and colorful instrumentation make it a favorite of jazz fans and dancers alike. Shaw’s innovative and virtuosic clarinet playing, combined with his band’s tight and swinging arrangements, make the song a high point of the big band era. The song’s Spanish lyrics, which describe the intensity of love and desire, add to its exotic and sensual allure.

25. Till The End Of Time – Perry Como / Les Brown / Dick Haymes

“Till The End Of Time” is a romantic ballad that was popularized by several artists in the 1940s, including Perry Como, Les Brown, and Dick Haymes. The song’s sentimental lyrics, which describe a love that will endure forever, struck a chord with audiences during World War II and became a classic of the era. The song’s slow tempo, lush orchestration, and emotive vocals create a nostalgic and romantic atmosphere that perfectly captures the spirit of the time. Each artist brings their unique style and interpretation to the song, making each version a memorable tribute to one of the most beloved ballads of the 1940s.

26. Lover Man (Oh Where Can You Be) – Billie Holiday / Sarah Vaughan

“Lover Man (Oh Where Can You Be)” is a soulful and poignant ballad that was popularized by jazz vocalists Billie Holiday and Sarah Vaughan in the 1940s. The song’s haunting melody and melancholic lyrics, which express the singer’s longing for a lost love, make it a quintessential torch song of the era. Both Holiday and Vaughan bring their unique vocal styles and interpretations to the song, imbuing it with their own personal touch of emotion and sensitivity.

27. Moonlight Cocktail – Glenn Miller

“Moonlight Cocktail” is a cheerful and upbeat swing tune that was popularized by Glenn Miller and his orchestra in the 1940s. The song’s catchy melody, bright horns, and driving rhythm make it a favorite of swing dancers and big band enthusiasts. The song’s lyrics, which describe a refreshing and satisfying cocktail, add to its lighthearted and carefree vibe. Miller’s polished and precise arrangements, along with his band’s tight and swinging performances, make the song a testament to the popularity and influence of the big band sound in the 1940s.

28. Stormy Weather – Lena Horne

“Stormy Weather” is a classic jazz standard that was made famous by singer and actress Lena Horne in the 1940s. The song’s mournful melody and lyrics describe a person’s feelings of sadness and despair during a turbulent period in their life. Horne’s soulful and expressive vocal performance, combined with the song’s lush orchestration, creates a powerful emotional impact that resonates with listeners to this day.

29. This Land Is Your Land – Woody Guthrie

“This Land Is Your Land” is a folk song written and performed by Woody Guthrie in the 1940s. The song’s lyrics express Guthrie’s love and appreciation for the natural beauty and diversity of the United States, as well as his desire for unity and equality among all its citizens. The song has become an iconic symbol of American folk music and has been covered by countless artists over the years. Its simple and catchy melody, along with its powerful message of inclusivity and patriotism, continue to inspire and unite people of all backgrounds and ages.

30. You Are My Sunshine – Jimmie Davis

“You Are My Sunshine” is a classic country song written by Jimmie Davis in the 1930s. The song’s cheerful melody and sweet lyrics express a deep affection and love for someone special in one’s life. The song has been covered by many artists over the years and has become a beloved classic in the world of country music. Its simple yet heartfelt message of love and devotion continues to resonate with listeners of all ages.

31. That Lucky Old Sun – Frankie Laine / Vaughn Monroe

“That Lucky Old Sun” is a popular song that was first recorded by Frankie Laine in 1949. The song’s lyrics describe a person’s longing for a better life and their desire to escape the hardships and struggles of their current situation. The song’s melancholic melody and haunting lyrics create a sense of longing and yearning that touches the hearts of listeners. The song has been covered by many artists over the years, including Vaughn Monroe, and has become a beloved classic in the world of popular music. Its powerful message of hope and resilience in the face of adversity continues to inspire listeners today.

32. (I Love You) For Sentimental Reasons – Nat “King” Cole / Eddy Howard / Dinah Shore

“(I Love You) For Sentimental Reasons” is a classic love song that has been covered by many artists over the years. Nat “King” Cole’s version is perhaps the most well-known, with his smooth vocals and jazzy instrumentation creating a romantic and nostalgic mood. The song’s lyrics express the deep emotions of love and devotion, as the singer reminisces about a past love and the memories they shared together. The song’s timeless appeal and universal themes have made it a beloved classic in the world of popular music.

33. (I’ve Got A Gal In) Kalamazoo – Glenn Miller (Marion Hutton & the Modernaires)

“(I’ve Got A Gal In) Kalamazoo” is a fun and upbeat swing song that was popularized by Glenn Miller and his orchestra in the 1940s. The song’s catchy melody and playful lyrics tell the story of a man who has found love in the town of Kalamazoo and can’t wait to go back and see his sweetheart. The song features lively vocal harmonies and a swinging big band sound that captures the energy and excitement of the era. The song has become a beloved classic in the world of swing and big band music, and continues to be a favorite among music lovers of all ages.

34. Don’t Sit Under The Apple Tree – Glenn Miller / Andrews Sisters

“Don’t Sit Under The Apple Tree” is a swing song written by Lew Brown, Charles Tobias, and Sam H. Stept in 1942. The song was originally titled “Anywhere the Bluebird Goes” and was featured in the Broadway musical Yokel Boy. It became popular during World War II as a morale-boosting tune, and the Glenn Miller Orchestra’s version with the Andrews Sisters on vocals became a hit. The song’s lyrics tell the story of a woman who warns her man not to cheat on her while he’s away at war, urging him to stay faithful and not sit under the apple tree with anyone else. The song’s catchy melody and upbeat tempo make it a timeless classic.

35. Ac-Cent-Tchu-Ate The Positive – Johnny Mercer / Bing Crosby & the Andrews Sisters

“Ac-Cent-Tchu-Ate The Positive” is a popular song with music by Harold Arlen and lyrics by Johnny Mercer. The song was written in 1944 and became a hit for Johnny Mercer and the Pied Pipers. The song’s message is one of positivity and encourages people to focus on the good things in life. The lyrics advise listeners to “accentuate the positive, eliminate the negative” and to “latch on to the affirmative.” The song became popular during World War II and was seen as a morale-boosting tune. Bing Crosby and the Andrews Sisters also had a hit with their version of the song, which features their trademark harmonies and a swing-style arrangement. The song’s upbeat melody and catchy lyrics have made it a popular tune for generations.

36. Maria Elena – Jimmy Dorsey / Wayne King

“Maria Elena” is a romantic song that was originally composed in 1932 by Lorenzo Barcelata, a Mexican composer. The song gained popularity after it was recorded in the early 1940s by bandleader Jimmy Dorsey and his orchestra. The instrumental version features a beautiful melody played on the saxophone and an upbeat rhythm section. Wayne King also recorded a popular version of the song, featuring vocals by Juan Arvizu. The song has been covered by many other artists in various languages, and its popularity has endured throughout the years.

37. A String Of Pearls – Glenn Miller

“A String of Pearls” is a popular big band jazz instrumental that was composed by Jerry Gray and recorded by Glenn Miller and his orchestra in 1941. The song features a memorable melody played by the saxophones and trumpets, backed by a swinging rhythm section. The song became one of Miller’s biggest hits and is often considered one of the most iconic big band recordings of all time. The song has been covered by many other artists and has appeared in numerous films, TV shows, and commercials.

38. The Gypsy – Ink Spots / Dinah Shore / Sammy Kaye (Mary Marlow)

“The Gypsy” is a song that was first popularized by The Ink Spots, and later covered by Dinah Shore and Sammy Kaye. The song is a romantic ballad that tells the story of a mysterious gypsy who captures the heart of the narrator. The haunting melody and smooth vocals make it a timeless classic, and it has been covered by many artists over the years.

39. Manana (Is Soon Enough For Me) – Peggy Lee

“Manana (Is Soon Enough For Me)” is a lively and upbeat song by Peggy Lee, with a Latin-inspired rhythm and catchy lyrics. The song speaks to the laid-back attitude of taking life as it comes and not rushing into anything. Peggy Lee’s smooth and sultry voice perfectly captures the carefree spirit of the song, making it a popular hit and a classic example of 1940s pop music.

40. Near You – Francis Craig / Andrews Sisters / Larry Green / Alvino Rey

“Near You” was a popular song in the 1940s and remains a timeless classic today. The song was written in 1940 by Francis Craig and Kermit Goell and was recorded by Craig’s orchestra in 1947, becoming an instant hit. The song’s simple melody and heartfelt lyrics about being close to someone special struck a chord with listeners, and it spent several weeks at the top of the Billboard charts. The Andrews Sisters, Larry Green, and Alvino Rey also recorded their versions of the song. “Amapola,” on the other hand, was a Spanish-language song written by Joseph Lacalle in 1924. Jimmy Dorsey’s 1941 version, featuring vocalists Bob Eberly and Helen O’Connell, became one of the most popular recordings of the song. Its catchy tune and romantic lyrics about a beautiful flower (amapola in Spanish) have made it a beloved classic.

41. Amapola – Jimmy Dorsey (Bob Eberly & Helen O’Connell)

“Amapola” is a beautiful and romantic song that was written by the Spanish composer José María Lacalle García in 1924. It became popular in the United States after being recorded by various artists, including the Jimmy Dorsey Orchestra with Bob Eberly and Helen O’Connell on vocals. The song features a soft and gentle melody that perfectly complements the romantic lyrics about a flower that represents the love between two people. The smooth vocals of Eberly and O’Connell and the dreamy arrangement by Dorsey make “Amapola” a timeless classic that still resonates with listeners today.

42. Peg O’ My Heart – Harmonicats / Buddy Clark / Three Suns

“Peg O’ My Heart” is a popular song composed by Alfred Bryan and Fred Fisher in 1913, and it has been recorded by numerous artists over the years. The versions by the Harmonicats, Buddy Clark, and the Three Suns in the 1940s were particularly popular, featuring the song’s memorable melody played on harmonica, crooned in a romantic ballad style, and performed instrumentally on an accordion and guitar, respectively.

43. Pennsylvania 6-5000 – Glenn Miller

“Pennsylvania 6-5000” is a swinging tune from the Glenn Miller Orchestra, named after the phone number of the Hotel Pennsylvania in New York City. The song’s catchy rhythm and melody were made even more memorable by the energetic trumpet solo played by Miller himself, as well as the lively call-and-response vocals of the Modernaires. The song became a hit and has since become a beloved classic, symbolizing the vibrant and upbeat spirit of the swing era.

44. Pistol Packin’ Mama – Al Dexter / Bing Crosby & the Andrews Sisters

“Pistol Packin’ Mama” is a classic World War II-era song that became a hit in 1943. The song is a fast-paced, rollicking tune with a catchy melody that is hard to forget. It tells the story of a woman who is tough, independent, and not afraid to use her gun if necessary. The song has a lighthearted and humorous tone, which helped make it popular with soldiers and civilians alike.

45. You’ll Never Know – Dick Haymes / Frank Sinatra

You’ll Never Know” is a timeless classic that speaks of the unspoken love and admiration for someone who has always been there for you. The song was first introduced by Alice Faye in the 1943 movie “Hello, Frisco, Hello,” but it was Dick Haymes and Frank Sinatra’s rendition that became the most popular. The song’s sweet and romantic melody, combined with the smooth vocals of the two legends, made it a hit in the 1940s and continues to be a favorite among listeners of all ages.

46. To Each His Own – Eddy Howard / Ink Spots / Freddy Martin / Modernaires

“To Each His Own” is a timeless ballad that has been covered by numerous artists throughout the years. The song is a beautiful and romantic ode to love, and Eddy Howard’s smooth and emotional delivery makes it one of the most memorable versions of the tune. The Ink Spots’ rendition is also noteworthy, with their trademark harmonies adding an extra layer of warmth and nostalgia to the song.

47. I Don’t Want To Set The World On Fire – Ink Spots / Hoarce Heidt / Tommy Tucker

“I Don’t Want to Set the World on Fire” is a romantic ballad that was popularized in the 1940s by The Ink Spots, Horace Heidt, and Tommy Tucker. The song’s sentimental lyrics express the desire of the singer to stay true to their loved one and not be distracted by fame or fortune. The song’s gentle melody and smooth harmonies make it a classic example of the romantic crooner style of the era. The song’s message of devotion and loyalty has resonated with listeners for generations.

48. Cool Water – Sons Of The Pioneers

“Cool Water” is a western ballad that was made famous in the 1940s by The Sons of the Pioneers. The song’s haunting melody and evocative lyrics tell the story of a cowboy who is lost in the desert and searching for water. The song’s imagery of the harsh and unforgiving landscape of the American West has made it a classic example of the cowboy song genre. The Sons of the Pioneers’ rich vocal harmonies and skilled musicianship helped to establish the song as a beloved standard of the western music canon.

49. As Time Goes By – Dooley Wilson

“As Time Goes By” is a classic love song that was made famous in the 1940s by Dooley Wilson in the movie “Casablanca.” The song’s romantic lyrics express the bittersweet longing and nostalgia of a love affair that has ended. The song’s tender melody and heartfelt delivery have made it a favorite of romantics everywhere. The song’s association with the iconic movie has helped to cement its place in the cultural consciousness as one of the greatest love songs of all time.

50. Opus No. 1 – Tommy Dorsey

“Opus No. 1” is a swing jazz instrumental that was made famous in the 1940s by Tommy Dorsey and his orchestra. The song’s dynamic melody and intricate arrangements showcase the virtuosity and skill of the band’s talented musicians. The song’s catchy hook and lively rhythm helped to make it a hit on the dance floors of America and established it as a classic example of the big band sound of the era. The song’s enduring popularity has ensured its place as a beloved standard of the swing jazz canon.

51. Rum And Coca-Cola – Andrews Sisters

“Rum and Coca-Cola” is a popular calypso song that was made famous in the 1940s by The Andrews Sisters. The song’s catchy melody and upbeat rhythm helped to make it a hit on the charts and on the dance floors of America. The song’s lyrics, which were controversial at the time, satirized the behavior of American soldiers stationed in the Caribbean during World War II. The song’s blend of Caribbean rhythms and American popular music helped to popularize calypso music in the United States and establish it as a unique and vibrant genre.

52. The Breeze And I – Jimmy Dorsey (Bob Eberly)

“The Breeze and I” is a romantic ballad that was made famous in the 1940s by Jimmy Dorsey and his orchestra, with vocals by Bob Eberly. The song’s lush melody and soaring vocals express the longing and desire of a lover for their beloved. The song’s intricate arrangement and dynamic shifts in mood and tempo make it a classic example of the romantic ballad style of the era. The song’s enduring popularity has ensured its place as a beloved standard of the American popular songbook.

53. We Three (My Echo, My Shadow, And Me) – Ink Spots / Tommy Dorsey (Frank Sinatra)

“We Three (My Echo, My Shadow, and Me)” is a hauntingly beautiful ballad that was made famous in the 1940s by The Ink Spots and Tommy Dorsey with vocals by Frank Sinatra. The song’s melancholy melody and reflective lyrics speak to the loneliness and isolation that can be experienced in life. The song’s intricate vocal harmonies and understated musical accompaniment create a sense of intimacy and emotional depth that make it a classic example of the romantic ballad style of the era. The song’s enduring popularity has ensured its place as a beloved standard of the American popular songbook.

54. I’ve Heard That Song Before – Harry James (Helen Forrest)

“I’ve Heard That Song Before” is a sweet and nostalgic ballad that was made famous in the 1940s by Harry James with vocals by Helen Forrest. The song’s catchy melody and upbeat rhythm evoke the feeling of reminiscing about happy memories from the past. The song’s lyrics speak to the power of music to transport us back in time and connect us with the people and moments that we hold dear. The song’s enduring popularity has ensured its place as a beloved standard of the American popular songbook and a cherished reminder of the joys of the past.

55. Baby It’s Cold Outside – Johnny Mercer & Margaret Whiting / Dinah Shore & Buddy Clark

“Baby, It’s Cold Outside” is a duet that was made famous in the 1940s by Johnny Mercer and Margaret Whiting, as well as Dinah Shore and Buddy Clark. The song’s playful call-and-response structure and flirtatious lyrics have made it a beloved classic of the American popular songbook. The song’s witty and sophisticated lyrics speak to the allure of romance and the playful banter that can exist between two people in love. The song’s enduring popularity has ensured its place as a holiday favorite and a beloved standard of the American popular songbook.

56. Tangerine – Jimmy Dorsey (Bob Eberly & Helen O’Connell)

“Tangerine” is a lively and upbeat song that was made famous in the 1940s by Jimmy Dorsey with vocals by Bob Eberly and Helen O’Connell. The song’s catchy melody and dynamic rhythm evoke the feeling of a carefree and joyful time. The song’s lyrics speak to the alluring power of a beautiful woman and the romantic feelings that she inspires. The song’s enduring popularity has ensured its place as a beloved standard of the American popular songbook and a cherished reminder of the exuberance and optimism of the era.

57. Buttons And Bows – Dinah Shore / Dinning Sisters

“Buttons and Bows” is a delightful song that was made famous in the 1940s by Dinah Shore and the Dinning Sisters. The song’s playful and whimsical lyrics speak to the appeal of a simpler and more carefree way of life. The song’s upbeat and catchy melody, paired with its clever lyrics, has made it a beloved classic of the American popular songbook. The song’s enduring popularity has ensured its place as a timeless reminder of the exuberance and optimism of the era.

58. Besame Mucho – Jimmy Dorsey (Bob Eberly & Kitty Kallen)

“Besame Mucho” is a beautiful and romantic song that was made famous in the 1940s by Jimmy Dorsey with vocals by Bob Eberly and Kitty Kallen. The song’s Spanish lyrics, which translate to “kiss me a lot,” speak to the power of love and the allure of a passionate romance. The song’s soaring melody and lush orchestration evoke the grandeur and intensity of a grand love affair. The song’s enduring popularity has ensured its place as a cherished standard of the American popular songbook and a testament to the enduring power of love.

59. ‘Round Midnight – Thelonius Monk

“‘Round Midnight” is a jazz standard composed by Thelonious Monk. The haunting and melancholic melody is considered a masterpiece of jazz composition and has been covered by countless musicians over the years. The song’s evocative and moody atmosphere speaks to the introspective and reflective qualities of jazz music, as well as to the enduring power of melancholy and nostalgia in the human experience.

60. I’ll Get By (As Long As I Have You) – Harry James (Dick Haymes) / Ink Spots

“I’ll Get By (As Long As I Have You)” is a classic song that was made famous in the 1940s by Harry James with vocals by Dick Haymes and the Ink Spots. The song’s lyrics speak to the power of love and the resilience of the human spirit in the face of adversity. The song’s upbeat and optimistic melody, paired with its hopeful and inspiring lyrics, has made it a beloved classic of the American popular songbook. The song’s enduring popularity has ensured its place as a testament to the enduring power of love and hope in the face of life’s challenges.

61. Cruising Down The River – Blue Barron / Russ Morgan / Jack Smith (Clark Sisters)

“Cruising Down The River” is a popular song that was released in 1946. The song was written by Eily Beadell and Nell Tollerton, with music by Nell Tollerton. The song became a hit for a number of artists, including Blue Barron, Russ Morgan, and Jack Smith with the Clark Sisters. The song has a cheerful and upbeat tone, with lyrics describing a romantic boat ride down the river. The song was popular during the post-war years and became a staple of easy-listening radio stations. It remains a beloved classic of the era and is often associated with the carefree spirit of the 1940s.

62. (There’ll Be Bluebirds Over) The White Cliffs Of Dover – Vera Lynn / Kay Kyser / Glenn Miller

“(There’ll Be Bluebirds Over) The White Cliffs Of Dover” is a classic wartime song that was released in 1942. The song was popularized by British singer Vera Lynn, who was known as the “Forces’ Sweetheart” for her performances for the troops during World War II. The song has a nostalgic and hopeful tone, with lyrics describing the beauty of the English countryside and the promise of peace after the war. The song became an anthem for soldiers and their families, and it remains a symbol of the resilience and optimism of the British people during the war.

63. Anniversary Song – Al Jolson / Dinah Shore / Guy Lombardo / Tex Beneke

“Anniversary Song” was originally a Russian song titled “Dorogoi dlinnoyu” (By the Long Road) written in 1946 by Al Jolson’s third wife, Yvonne De Carlo’s ex-husband, Saul Chaplin. Al Jolson recorded the song in 1947, and it became his final hit before he died. The song has since been covered by many artists, including Dinah Shore, Guy Lombardo, and Tex Beneke.

64. A Night In Tunisia – Dizzy Gillespie

“A Night in Tunisia” is a classic jazz standard written by trumpeter Dizzy Gillespie and pianist Frank Paparelli in 1942. The song’s distinctive melody and complex harmonies were inspired by Gillespie’s experiences listening to North African music while touring with Benny Carter’s band in the early 1940s. The song quickly became a jazz classic and has been covered by countless musicians, including Charlie Parker, Ella Fitzgerald, and Art Blakey. “A Night in Tunisia” remains a beloved piece of jazz history and a popular song for jazz ensembles to this day.

65. I Can Dream, Can’t I – Andrews Sisters

“I Can Dream, Can’t I” by Andrews Sisters is a beautiful ballad about the power of imagination and the hope that dreams bring. The song’s melody is gentle and soothing, and the Andrews Sisters’ harmonies are perfectly in sync. The lyrics describe the singer’s yearning for a better life and a brighter future, and the chorus’s repetition of the phrase “I can dream, can’t I?” serves as a powerful reminder that hope and imagination can help us overcome even the toughest challenges.

66. In The Blue Of The Evening – Tommy Dorsey (Frank Sinatra)

“In The Blue Of The Evening” by Tommy Dorsey (featuring Frank Sinatra) is a romantic and melancholic tune that captures the essence of love and longing. The song’s slow tempo and Sinatra’s smooth vocals create a dreamy atmosphere, and the lyrics describe the beauty and stillness of the night. The chorus, which repeats the phrase “In the blue of the evening, when you appear close to me dear,” expresses the singer’s desire to be reunited with his loved one and is a touching tribute to the power of love. Overall, this song is a timeless classic that continues to captivate audiences with its heartfelt message and beautiful melody.

67. Prisoner Of Love – Perry Como / Billy Eckstine / Ink Spots

“Prisoner of Love” has been covered by many artists, including Perry Como, Billy Eckstine, and Ink Spots. The song is a heart-wrenching ballad about the pain of unrequited love. The lyrics describe the singer’s longing for a love that will never be returned, and the melody conveys the sadness and despair that comes with such a situation. The chorus’s repetition of the phrase “I’m a prisoner of love” reinforces the song’s central theme and serves as a poignant reminder of the power of unfulfilled desire.

68. Sleepy Lagoon – Harry James

“Sleepy Lagoon” by Harry James is a soothing and romantic instrumental tune that became popular during the 1940s. The song’s mellow melody and gentle rhythms create a peaceful atmosphere, and James’s trumpet playing is simply mesmerizing. The song’s title refers to a popular swimming hole in California, and the music captures the tranquility and beauty of a lazy summer day. Overall, this song is a timeless classic that continues to evoke feelings of peace and serenity, making it a perfect choice for relaxation or reflection.

69. Blues In The Night – Woody Herman / Jimmie Lunceford / Dinah Shore

“Blues in the Night” has been covered by a variety of artists, including Woody Herman, Jimmie Lunceford, and Dinah Shore. The song is a moody and atmospheric blues tune that captures the essence of the night. The lyrics describe the darkness and mystery of the night and the sadness and loneliness that often accompany it. The melody is haunting and soulful, and the singers’ interpretations bring a unique and personal touch to the song. Overall, this song is a testament to the enduring appeal of the blues, and its evocative lyrics and music continue to resonate with listeners today.

70. A Tree In The Meadow – Margaret Whiting

“A Tree in the Meadow” by Margaret Whiting is a sentimental ballad that captures the beauty and simplicity of nature. The song’s melody is soft and soothing, and Whiting’s voice is gentle and tender. The lyrics describe the life cycle of a tree, from its humble beginnings to its eventual demise, and serve as a metaphor for the passage of time and the inevitability of change. The song’s message of acceptance and appreciation for the natural world is timeless, and its melody and lyrics continue to inspire and move listeners today.

71. Don’t Get Around Much Anymore – Ink Spots / Duke Ellington / Glen Gray

“Don’t Get Around Much Anymore” has been covered by many artists, including Ink Spots, Duke Ellington, and Glen Gray. The song is a classic jazz tune that captures the joy and excitement of socializing and going out on the town. The lyrics describe the singer’s decision to stay home instead of going out, and the melody is lively and upbeat, with a swinging rhythm that is typical of the big band era. The chorus’s repetition of the phrase “Don’t get around much anymore” adds a touch of nostalgia and serves as a reminder of the passing of time.

72. Daddy – Sammy Kaye

“Daddy” by Sammy Kaye is a sweet and sentimental tune that captures the love and affection between a father and his daughter. The song’s melody is gentle and soothing, and Kaye’s vocals are warm and heartfelt. The lyrics describe the unconditional love and support that a father provides for his child, and the chorus’s repetition of the phrase “Daddy, you’ve been a mother to me” emphasizes the importance of a father’s role in a child’s life. Overall, this song is a touching tribute to the bond between a father and his child and remains a beloved classic today.

73. Let It Snow! Let It Snow! Let It Snow! – Vaughn Monroe

“Let It Snow! Let It Snow! Let It Snow!” by Vaughn Monroe is a classic Christmas song that has become a holiday favorite. The song’s upbeat tempo and catchy melody are infectious, and the lyrics celebrate the joys of winter and the excitement of spending time with loved ones. The chorus’s repetition of the phrase “Let it snow” adds a touch of whimsy and serves as a reminder of the simple pleasures of the season. Overall, this song is a festive and fun tune that captures the spirit of the holidays and continues to be enjoyed by generations of listeners.

74. Oh! What It Seemed To Be – Frankie Carle / Frank Sinatra / Helen Forrest & Dick Haymes

“Oh! What It Seemed To Be” has been covered by a variety of artists, including Frankie Carle, Frank Sinatra, and Helen Forrest & Dick Haymes. The song is a romantic ballad that captures the nostalgia and longing of lost love. The lyrics describe a past relationship and the bittersweet memories that remain, and the melody is tender and soulful, with a slow, languid rhythm that conveys a sense of yearning. The singers’ interpretations bring their unique and personal touches to the song, but all versions share a sense of wistful melancholy that makes it a classic ballad of the big band era.

75. Imagination – Glenn Miller / Tommy Dorsey / Ella Fitzgerald

“Imagination” has been covered by a variety of artists, including Glenn Miller, Tommy Dorsey, and Ella Fitzgerald. The song is a romantic ballad that captures the power of imagination and the ability to escape reality through the power of the mind. The lyrics describe the singer’s desire to escape the world and live in a dream world of their own creation, and the melody is soft and dreamy, with a slow, gentle rhythm that is typical of the big band era. The singers’ interpretations bring their unique and personal touches to the song, but all versions share a sense of dreaminess and a yearning for a more ideal world.

76. There! I’ve Said It Again – Vaughn Monroe / Jimmy Dorsey (Teddy Walters)

“There! I’ve Said It Again” has been covered by Vaughn Monroe and Jimmy Dorsey (Teddy Walters). The song is a romantic ballad that captures the longing and vulnerability of love. The lyrics describe the singer’s confession of their feelings to their lover, and the melody is soft and tender, with a slow, languid rhythm that conveys a sense of vulnerability and tenderness. The singers’ interpretations bring their unique and personal touches to the song, but all versions share a sense of emotional honesty and a recognition of the risks and rewards of love. Overall, this song is a touching and heartfelt ballad that remains a beloved classic today.

77. Comin’ In On A Wing And A Prayer – Song Spinners / Willie Kelly

“Comin’ In On A Wing And A Prayer” has been covered by Song Spinners and Willie Kelly. The song is a patriotic ballad that reflects on the bravery and sacrifice of American soldiers during World War II. The lyrics describe a bomber plane returning home after a mission, barely making it back and depending on faith and luck to survive. The melody is upbeat and catchy, with a swinging rhythm that is typical of the big band era. The singers’ interpretations bring their unique and personal touches to the song, but all versions share a sense of pride and admiration for the men and women who fought for their country.

78. Smoke! Smoke! Smoke! (That Cigarette) – Tex Williams

“Smoke! Smoke! Smoke! (That Cigarette)” by Tex Williams is a novelty song that reflects on the dangers of smoking and the addictive nature of tobacco. The lyrics are humorous and tongue-in-cheek, with references to various health problems associated with smoking. The melody is upbeat and lively, with a catchy rhythm that is typical of Western swing music. The song became a hit during the 1940s, when smoking was still widely accepted and the health risks were not yet widely understood. Overall, this song is a lighthearted and fun tune that reflects the cultural attitudes of the time.

79. The Old Lamp-Lighter – Sammy Kaye / Kay Kyser

“The Old Lamp-Lighter” has been covered by Sammy Kaye and Kay Kyser. The song is a sentimental ballad that reflects on the comfort and warmth of a lighted lamp in the darkness of night. The lyrics describe a man who lights street lamps every night and the feelings of safety and security that his work brings to the community. The melody is soft and gentle, with a slow, romantic rhythm that is typical of the big band era. The singers’ interpretations bring their unique and personal touches to the song, but all versions share a sense of nostalgia and sentimentality for simpler times

80. When You Wish Upon A Star – Cliff Edwards / Glenn Miller / Guy Lombardo

“When You Wish Upon A Star” has been covered by Cliff Edwards, Glenn Miller, and Guy Lombardo. The song is a beloved Disney classic that captures the hope and optimism of childhood dreams. The lyrics encourage listeners to pursue their dreams and believe in the power of imagination to make them come true. The melody is gentle and uplifting, with a slow, dreamy rhythm that reflects the song’s message of hope and wonder. The singers’ interpretations bring their unique and personal touches to the song, but all versions share a sense of enchantment and wonder that make it a beloved classic.

81. Open The Door, Richard – Count Basie / Three Flames / Dusty Fletcher

“Open The Door, Richard” has been covered by Count Basie, Three Flames, and Dusty Fletcher. The song is a humorous and catchy tune that tells the story of a man named Richard who can’t seem to get home because his friend won’t let him in. The lyrics are full of playful wordplay and comic situations, making it a popular choice for live performances and radio broadcasts. The melody is upbeat and jazzy, with a swinging rhythm that reflects the playful nature of the song. The singers’ interpretations bring their unique and personal touches to the song, but all versions share a sense of fun and whimsy that make it a classic.

82. Is You Is Or Is You Ain’t (Ma’ Baby) – Louis Jordan / Bing Crosby & the Andrews Sisters

“Is You Is Or Is You Ain’t (Ma’ Baby)” has been covered by Louis Jordan and Bing Crosby & the Andrews Sisters. The song is a playful and flirtatious tune that asks the age-old question of whether or not a lover is still interested. The lyrics are full of clever wordplay and double entendres, making it a popular choice for live performances and radio broadcasts. The melody is upbeat and jazzy, with a swinging rhythm that reflects the playful nature of the song. The singers’ interpretations bring their unique and personal touches to the song, but all versions share a sense of fun and romance that make it a classic.

83. Shoo-Shoo Baby – Andrews Sisters / Ella Mae Morse

“Shoo-Shoo Baby” has been covered by Andrews Sisters and Ella Mae Morse. The song is a lively and upbeat tune that tells the story of a woman trying to get her man to take her home. The lyrics are full of playful wordplay and flirty lines, making it a popular choice for live performances and radio broadcasts. The melody is catchy and jazzy, with a swinging rhythm that reflects the playful nature of the song. The singers’ interpretations bring their unique and personal touches to the song, but all versions share a sense of fun and flirtatiousness that make it a classic.

84. Linda – Ray Noble (Buddy Clark) / Charlie Spivak

“Linda” has been covered by Ray Noble (Buddy Clark) and Charlie Spivak. The song is a romantic and sentimental ballad that tells the story of a man who is deeply in love with a woman named Linda. The lyrics are full of romantic imagery and heartfelt expressions of love, making it a popular choice for slow dances and romantic settings. The melody is lush and romantic, with soaring strings and gentle instrumentation that perfectly capture the emotions of the song. The singers’ interpretations bring their unique and personal touches to the song, but all versions share a sense of tenderness and passion that make it a classic.

85. Into Each Life Some Rain Must Fall – Ella Fitzgerald & the Ink Spots

“Into Each Life Some Rain Must Fall” is a classic duet performed by Ella Fitzgerald and the Ink Spots. The song is a melancholy ballad that explores the ups and downs of life, emphasizing the inevitability of difficult times. The lyrics are full of poetic imagery and metaphors, making it a popular choice for emotional performances and reflective moments. The melody is soft and gentle, with a soothing rhythm that reflects the introspective nature of the song. The singers’ interpretations bring their unique and personal touches to the song, but the combination of Fitzgerald’s sweet and soulful voice with the Ink Spots’ harmonies creates a timeless classic.

86. Jukebox Saturday Night – Glenn Miller (Marion Hutton, Tex Beneke & the Modernaires)

“Jukebox Saturday Night” is a popular song performed by Glenn Miller with vocals by Marion Hutton, Tex Beneke, and the Modernaires. The song is an upbeat and lively tune that celebrates the joys of music and dancing on a Saturday night. The lyrics are full of references to popular songs and artists of the time, making it a popular choice for dance parties and social gatherings. The melody is fast-paced and swinging, with a driving rhythm that perfectly captures the excitement of a night out on the town. The singers’ performances are full of energy and enthusiasm, making it a classic example of the big band sound.

87. Chattanoogie Shoe Shine Boy – Red Foley

“Chattanoogie Shoe Shine Boy” is a classic country and western song that was first recorded by Red Foley in 1950. The song tells the story of a young shoeshine boy in Chattanooga, Tennessee, who works hard shining shoes all day long, but still finds time to have fun and enjoy life. The upbeat tempo and catchy melody of the song, along with its playful lyrics, made it an instant hit, and it quickly became one of the most popular country songs of the era. “Chattanoogie Shoe Shine Boy” has since been covered by many other artists, and its enduring popularity has made it a beloved classic of the country and western genre.

88. Some Enchanted Evening – Perry Como / Bing Crosby / Jo Stafford / Frank Sinatra

“Some Enchanted Evening” is a classic romantic song from the musical South Pacific. Written by Rodgers and Hammerstein, it tells the story of two people falling in love and hoping to spend the rest of their lives together. The song has been covered by numerous artists over the years, including Perry Como, Bing Crosby, Jo Stafford, and Frank Sinatra. It is known for its beautiful melody and touching lyrics, which capture the feeling of falling in love and the hope and optimism that come with it. The song remains a popular choice for weddings and other romantic occasions to this day.

89. Rag Mop – Ames Brothers / Johnnie Lee Wills

“Rag Mop” was a hit song for The Ames Brothers and Johnnie Lee Wills in 1950. The song is an upbeat novelty tune that uses the term “rag mop” as a metaphor for a person’s unkempt appearance. The song features catchy call-and-response lyrics and a swinging melody that became popular with listeners. “On The Atchison, Topeka and Santa Fe” is a lively tune written by Harry Warren and Johnny Mercer. The song was recorded by Johnny Mercer and Bing Crosby and became a hit in 1945. The lyrics describe a train journey along the Atchison, Topeka and Santa Fe Railway and celebrate the excitement and romance of travel. The song features a bouncy melody, intricate harmonies, and a memorable chorus that has made it a classic of the swing era.

90. On The Atchison, Topeka And Santa Fe – Johnny Mercer / Bing Crosby

“On The Atchison, Topeka And Santa Fe” is a classic American song, originally written by Harry Warren and Johnny Mercer for the 1946 film “The Harvey Girls.” The song became a hit and was later recorded by Bing Crosby and other popular singers of the time. The upbeat tempo and catchy lyrics describe the excitement and adventure of traveling by train across the American West. Johnny Mercer’s clever wordplay and Bing Crosby’s smooth vocals make this song a timeless favorite that evokes feelings of nostalgia and wanderlust. “On The Atchison, Topeka And Santa Fe” is a charming and cheerful tune that captures the spirit of mid-century America.

91. Praise The Lord And Pass The Ammunition! – Kay Kyser / Merry Macs

“Praise The Lord And Pass The Ammunition!” is a patriotic and spirited song that was written by Frank Loesser in 1942, shortly after the United States entered World War II. The song became an instant hit and was recorded by various artists, including Kay Kyser and the Merry Macs. The lyrics express a call to action for soldiers and civilians alike to join the fight against the enemy, with a mix of humor and urgency. The catchy chorus of “Praise the Lord and pass the ammunition” became a popular catchphrase during the war and continues to be a cultural reference to this day. “Praise The Lord And Pass The Ammunition!” is a rousing and inspiring song that reflects the wartime spirit and serves as a reminder of the sacrifices made by those who fought for freedom.

92. I’ll Walk Alone – Dinah Shore / Martha Tilton / Mary Martin

“I’ll Walk Alone” is a poignant and bittersweet ballad that was written by Jule Styne and Sammy Cahn in 1944. The song became popular during World War II and was recorded by several female vocalists, including Dinah Shore, Martha Tilton, and Mary Martin. The lyrics tell the story of a person who is facing loneliness and heartbreak, but who refuses to give up hope and remains determined to find love and happiness. The melody is gentle and melancholic, with a simple yet beautiful arrangement that highlights the emotion of the lyrics. “I’ll Walk Alone” is a timeless classic that speaks to the human experience of love and loss, and the power of resilience in the face of adversity.

93. Ballerina – Vaughn Monroe / Buddy Clark / Bing Crosby

“Ballerina” is a romantic and dreamy song that was written by Carl Sigman and Sidney Keith Russell in 1947. The song was recorded by several popular artists of the time, including Vaughn Monroe, Buddy Clark, and Bing Crosby. The lyrics compare a beautiful ballerina to a delicate flower, and express the singer’s admiration and love for her. The melody is gentle and nostalgic, with a lush orchestral arrangement that enhances the romantic atmosphere of the song. “Ballerina” is a timeless classic that captures the essence of old Hollywood romance, and continues to be a favorite among fans of classic American music.

94. I’m looking Over A Four-Leaf Clover – Art Mooney / Russ Morgan / Alvino Rey

“I’m Looking Over a Four-Leaf Clover” is a cheerful and optimistic song that was popularized in the 1940s by Art Mooney, Russ Morgan, and Alvino Rey. The song’s catchy melody and upbeat lyrics celebrate the joy and wonder of finding a four-leaf clover, a symbol of good luck and fortune. The song’s simple but effective arrangement and lively tempo make it a classic example of the upbeat pop music of the era.

95. Jersey Bounce – Benny Goodman / Jimmy Dorsey

“Jersey Bounce” is a swing jazz instrumental that was popularized in the 1940s by Benny Goodman and Jimmy Dorsey. The song’s lively melody and dynamic rhythm showcase the virtuosity and skill of the two bandleaders and their ensembles. The song’s name is a reference to the popular dance craze of the time, the Jersey bounce, which was characterized by its bouncy and energetic steps. The song’s catchy hook and infectious rhythm helped to make it a hit on the dance floors of America and establish it as a classic of the swing era.

96. Mule Train – Frankie Laine / Tennessee Ernie Ford / Bing Crosby / Vaughn Monroe

“Mule Train” is an iconic country and western song that was made famous in the 1940s by Frankie Laine, Tennessee Ernie Ford, Bing Crosby, and Vaughn Monroe. The song’s driving rhythm and energetic vocals evoke the image of a team of mules pulling a wagon across the prairie. The song’s lyrics tell the story of a hardworking and determined mule train driver who is proud of his job and his team of mules. The song’s popularity helped to establish Frankie Laine as a major recording artist and cemented the song’s place in the country and western canon.

97. G.I. Jive – Louis Jordan / Johnny Mercer

“G.I. Jive” is a swing jazz song that was popularized during World War II by Louis Jordan and Johnny Mercer. The song’s catchy melody and upbeat lyrics celebrate the music and dance culture of the American military during the war. The song’s lyrics namecheck popular dances of the time, such as the jitterbug and the Lindy hop, and pay tribute to the talented musicians who played for the troops. The song’s joyful message and infectious rhythm helped to lift the spirits of soldiers and civilians alike during a difficult time in American history.

98. You Call Everybody Darlin’ – Al Trace / Andrews Sisters / Anne Vincent

“You Call Everybody Darlin'” is a classic love song that was popularized in the 1940s by Al Trace, the Andrews Sisters, and Anne Vincent. The song’s catchy melody and playful lyrics tell the story of a person who is so in love that they mistakenly think everyone they meet is also in love with them. The Andrews Sisters’ signature harmonies add to the song’s charm and make it a memorable and enjoyable piece of music.

99. Maybe – Ink Spots

“Maybe” is a romantic ballad that was originally recorded by The Ink Spots in 1940. The song’s slow tempo, soothing harmonies, and poetic lyrics make it a classic example of the romantic crooner style of the era. The Ink Spots’ smooth vocals and skilled musicianship helped to make the song a hit, and it has since become a beloved standard of the Great American Songbook. The song’s message of hope and optimism in the face of uncertainty and doubt has resonated with generations of listeners.

100. Der Fuehrer’s Face – Spike Jones (Carl Grayson & Willie Spicer)

“Der Fuehrer’s Face” is a satirical song that was popularized during World War II by Spike Jones and His City Slickers. The song is a sarcastic commentary on the regime of Adolf Hitler and the Nazi Party in Germany, depicting the hardships and absurdities of life under their rule. The song’s lyrics, sung by Carl Grayson and Willie Spicer, poke fun at the propaganda and brainwashing tactics used by the Nazis and paint a vivid picture of the bleak and oppressive atmosphere of wartime Germany. The song’s upbeat melody and catchy chorus make it a memorable and entertaining piece of wartime propaganda.