Frank Sinatra is more than just a singer—he’s a cultural icon, a timeless voice that continues to captivate audiences decades after his heyday. Known as “Ol’ Blue Eyes,” Sinatra’s smooth baritone, impeccable phrasing, and larger-than-life charisma cemented his place as one of the greatest entertainers of all time. From jazz and swing to romantic ballads, Sinatra’s music transcends generations, offering something for everyone. Whether he was belting out anthems of ambition or crooning tender love songs, Sinatra had an unparalleled ability to make listeners feel every word.
In celebration of his incredible legacy, we’ve rounded up the top 10 most popular Frank Sinatra songs of all time—tracks that have stood the test of time and continue to define what it means to be a legend. These songs aren’t just hits; they’re cultural milestones, each telling a unique story while showcasing Sinatra’s extraordinary artistry. From the bold swagger of “New York, New York” to the poignant reflection of “It Was a Very Good Year,” each track captures a different facet of Sinatra’s genius. So, pour yourself a glass of your favorite drink, sit back, and let’s dive into the music that made Frank Sinatra an enduring symbol of elegance, passion, and style.
1. “My Way” (1969)
Few songs embody the spirit of individuality and resilience like Frank Sinatra’s iconic anthem, “My Way.” Released in 1969, this timeless classic was adapted by Paul Anka from the French song “Comme d’habitude” and reimagined into a declaration of self-determination. Its reflective lyrics speak of a life lived without regret, a message that resonated deeply with Sinatra’s audience and continues to inspire listeners worldwide. Sinatra’s grand yet deeply personal delivery gives the song an emotional gravity, making it one of his most beloved performances. “My Way” quickly became a global phenomenon and a staple of his legacy, inspiring countless covers across genres. For many, it transcends music, becoming a statement of courage and triumph that stands the test of time.
2. “Fly Me to the Moon” (1954)
“Fly Me to the Moon,” written by Bart Howard in 1954, soared to new heights when Frank Sinatra recorded it in 1964 alongside Count Basie and his orchestra. Arranged by Quincy Jones, this jazzy rendition turned the romantic tune into a swinging celebration of love and adventure. Sinatra’s effortlessly smooth vocals combined with Basie’s lively instrumentation created a timeless masterpiece. The song’s legacy reached another level when it became linked to the Apollo 11 moon landing, where it was famously played on the lunar surface. This association cemented its symbolism of exploration and wonder. Sinatra’s version remains definitive, capturing the joy of romance and the magic of reaching for the stars.
3. “New York, New York” (1977)
Bold, brassy, and bursting with energy, “New York, New York” became a quintessential Sinatra classic when he recorded it in 1979. Originally written for Martin Scorsese’s 1977 film of the same name, the song’s vibrant arrangement and Sinatra’s inimitable swagger transformed it into an anthem of ambition and resilience. Its iconic opening line, “Start spreading the news,” instantly evokes the spirit of the city that never sleeps. Sinatra’s rendition radiates the excitement, grit, and allure of New York, making it a timeless love letter to the Big Apple. Whether you’re a New Yorker or not, the song’s infectious optimism is hard to resist.
4. “That’s Life” (1966)
Raw, soulful, and utterly captivating, “That’s Life” showcases Sinatra’s ability to channel profound emotion. Released in 1966, the song captures the rollercoaster of life with unflinching honesty. Its bluesy arrangement, featuring a soaring horn section, perfectly complements Sinatra’s commanding vocals. The defiant refrain, “I just pick myself up and get back in the race,” has become a rallying cry for perseverance, making it one of Sinatra’s most relatable and enduring songs. A chart-topping hit, “That’s Life” embodies the resilience of the human spirit, solidifying its place as a cornerstone of Sinatra’s legendary catalog.
5. “Strangers in the Night” (1966)
Released in 1966, “Strangers in the Night” became an instant hit and a signature Sinatra song. This romantic ballad, penned by Bert Kaempfert with English lyrics by Charles Singleton and Eddie Snyder, tells the story of love at first sight, perfectly suited to Sinatra’s smooth and velvety voice. The lush orchestration, complete with swooning strings, adds a layer of elegance to the heartfelt lyrics. Though Sinatra reportedly had mixed feelings about the song, it earned him two Grammy Awards and widespread acclaim. The playful “doo-be-doo-be-doo” outro remains an unforgettable hallmark of this enduring classic.
6. “Come Fly with Me” (1958)
“Come Fly with Me,” the breezy title track of Sinatra’s 1958 album, is an invitation to adventure and romance. Written by Jimmy Van Heusen and Sammy Cahn, the song captures the glamour of the jet-set era with its upbeat swing and playful lyrics. Sinatra’s charismatic delivery transports listeners to exotic locales, making them feel like they’re part of a grand escapade. Synonymous with Sinatra’s image as the ultimate entertainer, “Come Fly with Me” remains a vibrant testament to his ability to bring joy and wanderlust to every note.
7. “The Way You Look Tonight” (1936)
Originally written by Jerome Kern and Dorothy Fields for the 1936 Fred Astaire film Swing Time, “The Way You Look Tonight” found renewed elegance in Sinatra’s 1964 rendition. His warm and tender delivery paired with lush orchestration makes this version a standout. A favorite for weddings and romantic moments, the song exudes timeless beauty and charm. While many have covered this classic, Sinatra’s heartfelt performance continues to set the gold standard, evoking the magic of love with every listen.
8. “Luck Be a Lady” (1950)
From Broadway to big band glory, “Luck Be a Lady” was redefined by Sinatra in 1965. Originally written by Frank Loesser for the musical Guys and Dolls, Sinatra’s version elevates the song with a brassy arrangement and his larger-than-life persona. The song’s dramatic swings between confidence and desperation are perfectly embodied in Sinatra’s commanding performance. This thrilling number encapsulates the essence of the Rat Pack era and remains a staple of American popular music.
9. “I’ve Got You Under My Skin” (1936)
Sinatra’s 1956 rendition of Cole Porter’s “I’ve Got You Under My Skin” transformed the song into a definitive jazz standard. Featured on Songs for Swingin’ Lovers!, the lush Nelson Riddle arrangement is a masterpiece in itself, blending intricate brass sections with rhythmic sophistication. Sinatra’s smooth phrasing brings out the obsessive passion in Porter’s lyrics, culminating in a dramatic trombone solo that still dazzles. This track is a testament to Sinatra’s artistry and his ability to breathe new life into classics.
10. “It Was a Very Good Year” (1965)
Few songs delve into the poignancy of aging and reflection like Sinatra’s “It Was a Very Good Year.” Released in 1965 on the album September of My Years, this ballad, written by Ervin Drake, takes listeners on an emotional journey through cherished memories. Sinatra’s wistful delivery paired with Gordon Jenkins’ lush orchestral arrangement makes the song deeply moving. Its deliberate pacing and poetic lyrics allow each note to resonate, creating a profound listening experience. Winning a Grammy for Best Vocal Performance, it stands as one of Sinatra’s most introspective and enduring works.
Samuel Moore is a frequent contributor to Singers Room. Since 2005, Singersroom has been the voice of R&B around the world. Connect with us via social media below.
