Frank Sinatra’s 10 most famous songs ever – My Way only at No. 3

One of the most influential and recognised artists in history, Frank Sinatra was every musician’s main inspiration for generations.

Nicknamed “Ol’ Blue Eyes” and “The Chairman of the Board”, he rose to fame as a teen idol during World War II, transitioning later into a successful film actor and serious jazz singer. Throughout these eras, he managed to make himself known as one of the greatest singers of the 20th century, praised for his smooth baritone, emotional delivery, and charisma.

But which of his hits left the deepest mark in the digital age? Here, we take a look at Sinatra’s ten most successful songs on Spotify, ranked.

10- The Way You Look Tonight

232,205,556 streams

Originally by Fred Astaire for the film Swing Time, ‘The Way You Look Tonight’ and its romantic tones – expressing the singer’s admiration and love for his partner – were covered by Sinatra 28 years later, in 1964.

Before and after Sinara: The song had won an Academy Award for Best Original Song in 1936, and was later also covered by Tony Bennett, The Lettermen and Rod Stewart – but no version became more famous than Sinatra’s.

9- Come Fly With Me

237,048,968 streams

‘Come Fly With Me’ was released in 1958 and quickly reached the No. 1 of the Billboard Charts and was nominated for the Album of the Year category at the first ever Grammy Awards ceremony.

The song describes adventures in exotic places – that we are invited to visit with Sinatra – like Acapulco Bay, Bombay and Peru. ‘Come Fly With Me’ was also released as a duet with Latin music icon Luis Miguel.

8- Have Yourself a Merry Little Christmas

241,060,457 streams

Originally sung by Judy Garland in the 1944 MGM musical Meet Me in St. Louis, this wistful wartime ballad found new life in Sinatra’s smoother, more optimistic version recorded in 1957.

While Garland’s take leaned into melancholy, reflecting the emotional toll of war and separation, Sinatra asked for the lyrics to be slightly altered to make them more cheerful – reflecting his image as a comforting, reassuring voice for postwar America. The result is a classic holiday staple, revisited every December by listeners worldwide.

7- Strangers in the Night

374,484,425 streams

Possibly the most recognisable Sinatra hit of the 1960s, ‘Strangers in the Night’ won him three Grammy Awards, including Record of the Year in 1967.

Despite Sinatra reportedly not being fond of the track – calling it “a piece of s**t” in private – the sweeping orchestration and his effortless phrasing turned it into a defining late-career success. The song’s “doobie-doobie-doo” outro still makes some appearances in film and television.

6- Jingle Bells

332,521,749 streams

One of the oldest songs on this list in terms of origin, ‘Jingle Bells’ dates back to 1857 but has been reinvented dozens of times. Sinatra’s swing-infused 1957 rendition, featuring the Ralph Brewster Singers and Nelson Riddle’s orchestration, gave the carol a hip, mid-century remix.

Released on the A Jolly Christmas from Frank Sinatra album, his version is brisk, buoyant, and fun – fitting what postwar audiences might have wanted from their Christmas music. Decades later, it remains one of the most-played versions of the song each holiday season.

5- That’s Life

364,655,150 streams

A powerful anthem of resilience, ‘That’s Life’ was released in 1966 and quickly became one of Sinatra’s most personal statements. With its brass-heavy arrangement and bold, almost spoken delivery, Sinatra channelled every inch of his larger-than-life persona into the song’s message of perseverance.

It became especially popular among younger listeners rediscovering Sinatra through films like Joker (2019).

4- Somethin’ Stupid

439,915,717 streams

This charming father-daughter duet with Nancy Sinatra became the first and only father-daughter number one in Billboard Hot 100 history.

Originally written and recorded by folk duo Carson and Gaile, Sinatra’s 1967 version transformed it into a chart-topper, backed by lush strings and a sweet, conversational delivery. Some critics initially criticised the song’s simplicity, but its warm and intimate feel proved irresistible.

3- My Way

581,337,897 streams

The ultimate self-determination anthem, ‘My Way’ is arguably Sinatra’s most recognisable recording. The melody was lifted from a French song (Comme d’habitude), but with Paul Anka’s new English lyrics tailored specifically for Sinatra, it became a defining career tune.

Released in 1969, the song never hit number one in the US but spent an astonishing 75 weeks on the UK Singles Chart. Sinatra himself later had mixed feelings about it, saying he “hated” it for being overly self-indulgent, yet it’s hard to imagine a track more closely associated with his public image.

2- Let It Snow! Let It Snow! Let It Snow!

661,991,352 streams

Although ‘Let It Snow’ has been covered by nearly every singer of the time, Sinatra’s 1950 recording might be the gold standard. With a relaxed swing and the warm glow of holiday nostalgia, his version avoids the over-sentimentality of later renditions.

It’s playful, gently romantic, and endlessly replayable – helping explain its massive stream count every winter.

1- Fly Me to the Moon (In Other Words)

751,206,695 streams

First penned by Bart Howard in 1954 and originally sung by Kaye Ballard, it wasn’t until Sinatra’s 1964 version – arranged by Quincy Jones and backed by Count Basie’s orchestra – that ‘Fly Me to the Moon’ became the immortal jazz-pop classic we know today.

Sinatra’s rendition was so iconic that NASA played it during the Apollo 10 and Apollo 11 missions, linking it forever with humanity’s leap into space.