Frank Sinatra isn’t just a singer—he’s a legend. With a voice as smooth as fine whiskey and a charisma that could light up the biggest stages in the world, Sinatra defined an era of music that still resonates today. From the smoky jazz clubs of the 1940s to the glitz and glamour of Las Vegas, Ol’ Blue Eyes captivated audiences with his effortless charm and timeless songs. Whether he was belting out swinging big-band anthems or crooning heartfelt ballads, Sinatra had a way of making every lyric feel personal, every note unforgettable.
His music transcends generations, with songs that have become anthems of love, ambition, heartbreak, and resilience. Whether you’re dreaming of making it big in New York, New York, reminiscing about a lost summer romance, or declaring that you did it My Way, Sinatra’s voice is the soundtrack to life’s most defining moments. But which of his songs stand above the rest?
In this article, we count down the top 10 most popular Frank Sinatra songs of all time—the tracks that continue to inspire, move, and define what it means to be a true musical icon. So sit back, pour yourself a drink, and let’s dive into the magic of Sinatra’s greatest hits.
1. My Way (1969)
Arguably Frank Sinatra’s most iconic song, My Way is a powerful declaration of independence and self-reflection. Originally a French tune (Comme d’habitude), Paul Anka reimagined it with English lyrics that perfectly suited Sinatra’s persona. The song’s grand orchestration and heartfelt delivery create an emotional resonance that has made it a staple at farewell events, from retirement parties to funerals. Sinatra’s deep, measured vocals convey the wisdom of a life lived unapologetically, embracing both triumphs and regrets. Over the decades, My Way has been covered by countless artists, but none have captured its gravity quite like Sinatra.
2. Fly Me to the Moon (1954)
Originally penned by Bart Howard, this jazz classic found its definitive voice when Sinatra recorded it in 1964 with Count Basie’s orchestra under the arrangement of Quincy Jones. His swinging rendition gave the song an effortless cool, perfectly capturing the romanticism of space travel at the height of the Space Age. The song became forever linked to history when NASA played it during the Apollo missions, making it one of the first songs ever associated with lunar exploration. Whether in a jazz club or under a starlit sky, Fly Me to the Moon remains a timeless invitation to love and adventure.
3. New York, New York (1977)
Originally performed by Liza Minnelli for Martin Scorsese’s New York, New York, the song truly became legendary when Sinatra recorded it in 1980. With its brassy crescendos and soaring optimism, New York, New York is the ultimate anthem of ambition and the relentless energy of the city that never sleeps. Sinatra’s confident, full-throated delivery makes it an inspiring rallying cry for dreamers aiming for the top. Over the years, the song has become synonymous with both Sinatra and the city itself, frequently played at celebrations, parades, and even New York Yankees victories.
4. Strangers in the Night (1966)
A song of chance encounters and instant attraction, Strangers in the Night was originally composed by Bert Kaempfert before Sinatra transformed it into a worldwide hit in 1966. With its lush orchestration and gentle melody, the song tells the story of two people who meet by fate and find love in an instant. Though Sinatra was reportedly not fond of the track, it became one of his biggest hits, topping the Billboard charts and winning multiple Grammy Awards. The smooth, romantic feel of Strangers in the Night continues to make it a favorite among love songs.
5. I’ve Got You Under My Skin (1936, Sinatra’s version: 1956)
Written by Cole Porter in 1936, I’ve Got You Under My Skin became a jazz standard when Sinatra recorded his definitive version in 1956. Nelson Riddle’s dynamic arrangement builds the song from an intimate whisper to a thrilling big-band explosion, with Sinatra’s impeccable phrasing carrying the emotional intensity. The song perfectly captures the feeling of irresistible attraction—an obsession that lingers just beneath the surface. With its driving brass section and Sinatra’s effortless cool, I’ve Got You Under My Skin remains one of his most electrifying recordings.
6. The Way You Look Tonight (1936, Sinatra’s version: 1964)
Originally introduced in the Fred Astaire and Ginger Rogers film Swing Time, this Jerome Kern and Dorothy Fields classic found new life in 1964 with Sinatra’s smooth, romantic interpretation. His velvety vocals give the song a warm, timeless quality, making it a favorite for weddings and romantic moments. The lyrics capture the magic of a perfect moment—one where beauty, love, and admiration are frozen in time. Whether played during a slow dance or softly in the background, The Way You Look Tonight remains one of Sinatra’s most cherished love songs.
7. That’s Life (1963, Sinatra’s version: 1966)
A bold and bluesy declaration of resilience, That’s Life was first recorded by Marion Montgomery in 1963 before Sinatra made it his own in 1966. With a powerhouse brass section and raw, impassioned vocals, Sinatra delivers the song like a man who has seen life’s highs and lows and still refuses to stay down. Its lyrics about rolling with the punches and coming back stronger have resonated with listeners for decades. Whether played during tough times or moments of triumph, That’s Life is an anthem for anyone determined to keep going, no matter what.
8. Come Fly with Me (1957, Sinatra’s version: 1958)
Written specifically for Sinatra by Jimmy Van Heusen and Sammy Cahn, Come Fly with Me is the ultimate travel song. With its playful lyrics and lively big-band swing, the song paints a picture of effortless luxury and jet-setting adventure. As the opening track of his 1958 album of the same name, it set the tone for an era of sophisticated, globe-trotting cool. Sinatra’s performance brims with charm, making listeners feel like they’re being whisked away to an exotic destination. The song remains a classic for anyone who dreams of adventure and romance in faraway places.
9. Luck Be a Lady (1950, Sinatra’s version: 1963)
Originally written by Frank Loesser for the 1950 musical Guys and Dolls, Luck Be a Lady took on a new life when Sinatra recorded his version in 1963. With its high-stakes theme of gambling and fate, the song fits perfectly into Sinatra’s Vegas-era persona. His commanding vocals exude charisma and confidence, transforming the song into an anthem of risk and reward. Whether belted out in a casino or performed on stage, Luck Be a Lady is a thrilling number that embodies Sinatra’s signature style and swagger.
10. Summer Wind (1965, Sinatra’s version: 1966)
A wistful ballad about love and loss, Summer Wind was originally a German tune before Johnny Mercer adapted it into English lyrics. Sinatra’s 1966 recording captures the bittersweet nature of fleeting romance, with a relaxed yet deeply evocative delivery. The song’s gentle swing and melancholic undertones make it a perfect soundtrack for nostalgia—whether reminiscing about a past love or simply watching the seasons change. Over time, Summer Wind has become one of Sinatra’s most beloved songs, offering a beautiful, reflective take on the passage of time.
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.
