Frank Sinatra Songs: The Top 10 Ol' Blue Eyes Hits That Will Instantly Take You Back

Few artists have created a more enduring legacy of hits than Ol’ Blue Eyes himself, the legendary Frank Sinatra. His smooth resonant voice remains popular among music lovers of all generations, and Frank Sinatra songs are frequently heard in films, tv shows and music venues all over the world.

In fact, earlier this year a new restaurant opened in Nashville, Tennessee named Sinatra Bar & Lounge that features his music and the classy, elegant ambience that is synonymous with the singer who was known as "The Chairman of the Board" and a beloved member of Hollywood’s Rat Pack.

“It’s gorgeous,” Frank’s daughter, Tina Sinatra tells Woman's World of the new restaurant. “It’s cozy, but it still has an elegance to it, and it personifies [my father] because he’s more popular than ever. I think people will want to come here and be surrounded by his music. He’d be here if he were alive.” And of course, they always have Frank Sinatra songs adding to the wonderful place-out-of time atmosphere.

Sinatra’s talent catapulted him to the top of the music charts and paved the way for him to become an Oscar-winning actor as well. That legacy is also being celebrated in Sinatra The Musical, a play which is starring Tony Award winning actor Matt Doyle. Written by Tony Award winner Joe DiPietro, with Kathleen Marshall, three-time Tony Award winner, directing. The new show premieres at Birmingham Repertory Theatre, commonly called Birmingham Rep in England, and is running September 23 through October 28.

Here, in honor of the newest projects celebrating Frank Sinatra's legacy, we've gathered 10 of his most memorable and beloved songs for your listening enjoyment.

Top 10 Frank Sinatra songs

1. “One for My Baby (And One More for the Road)” (1947)

Penned by Harold Arlen and Johnny Mercer, this song was written for the 1943 movie musical The Sky’s the Limit. Originally performed by Fred Astaire, Sinatra recorded the song several times during his career, first in 1947 for a Columbia Records project, then in 1954 for the soundtrack of the film Young at Heart, in 1962 for Sinatra & Sextet: Live in Paris and again in 1966 for Sinatra at the Sands and finally in 1993 for his Duets album. In recent years, Sinatra’s version has resurfaced in Blade Runner 2049 and on an episode of The Marvelous Mrs. Maisel.

2. “Three Coins in the Fountain” (1954) Frank Sinatra songs

Written by Jule Styne and Sammy Cahn, this memorable song won the Academy Award for Best Original Song in 1955. The title refers to the beloved tradition of throwing coins into the Trevi Fountain in Rome and making a wish.

The song was written for the film Three Coins in the Fountain, which starred Clifton Webb, Dorothy McGuire and Jean Peters. Surprisingly, the songwriters weren’t able to read the script or screen the film before they had to write the song, but it worked just fine. In addition to Sinatra’s version, the song was also recorded by Dinah Shore, The Four Aces, Harry James, Vince Guaraldi, Sergio Franchi and Jack Jones.

3. “I’ve Got You Under my Skin” (1956)

Written by legendary songwriter Cole Porter, this song has been recorded by numerous artists including The Four Seasons, Bobby Caldwell and Neneh Cherry, but Sinatra’s rendition is considered by many to be the definitive version of the song. Songwriter Jimmy Webb has stated: “Frank seems to have co-invented a style of big band accompaniment that just took off like some big rocket. I could see it on his face, on stage, when the band started to blow on ‘I’ve Got You Under My Skin.’ He knew we were going to a place where man had never gone before.”

4. “Lady is a Tramp” (1957) Frank Sinatra songs

This song originated in the 1937 Rodgers & Hart musical Babes in Arms, but was also included in the 1957 film Pal Joey, starring Sinatra and Rita Hayworth. In the film Sinatra stars as Joey Evans and sings the song to Hayworth’s character Vera Simpson. In addition to Sinatra, the song has also been recorded by Ella Fitzgerald, Buddy Greco, Shirley Bassey and also by Tony Bennett and Lady Gaga for their 2011 album Duets II.

5. “Come Fly with Me” (1958)

This smooth hit was the title song of Frank’s best-selling 1958 album. It was written specifically for Sinatra by Jimmy Van Heusen and Sammy Cahn. The song became one of the most popular numbers during his concerts, and Sinatra also re-recorded it as a duet with Luis Miguel on his 1994 album Duets II. The song has been featured in numerous films, including Air America, Betsey’s Wedding, Raging Bull, Heartbreakers, Catch Me if You Can, Pan Am, Vegas Vacation and others.

6. “Strangers in the Night” (1966)

Written by Bert Kaempfert, Charles Singleton and Eddie Synder, “Strangers in the Night” hit No. 1 on both the Billboard Hot 100 and the Easy Listening charts. One of Ol’ Blue Eyes’ most recognizable classics, the song won Sinatra the Grammy for Best Male Pop Vocal Performance and the Grammy for Record of the Year, in addition to also earning a Grammy for Best Arrangement Accompanying a Vocalist or Instrumentalist for Ernie Freeman.

On an interesting note, country icon Glen Campbell played guitar on the song. Though it was a huge hit, Sinatra was often quoted as saying he never like the song and called it "the worst song he’d ever heard."

7. “That’s Life” (1966) Frank Sinatra songs

This upbeat treatise to surviving life’s ups and downs was written by Dean Kay and Kelly Gordon. Though it was first recorded by Marion Montgomery in 1963, Sinatra recorded it as the title track of his 1966 album and turned it into a hit, taking the song to the No. 4 spot on the Billboard Hot 100.

Over the years, the this is another one of the Frank Sinatra songs that has been recorded by numerous artists, among them Michael Bolton, Deana Martin, Shirley Bassey, James Brown, Michael Buble, David Lee Roth, Van Morrison and James Brown.

8. “My Way” (1969)

Though it has been recorded by Elvis Presley and Sid Vicious, among others, many consider Sinatra’s recording to be the definite version of this celebration of fortitude and independence. The lyrics were penned by pop star Paul Anka and were tailor made to celebrate Sinatra’s defiance and independence.

“At one o'clock in the morning, I sat down at an old IBM electric typewriter and said, 'If Frank were writing this, what would he say?’” Anka recalls of writing the song after a dinner with Sinatra and pals. “I started, metaphorically, ‘And now the end is near.’ I read a lot of periodicals, and I noticed everything was ‘my this’ and ‘my that.’  We were in the ‘me generation’ and Frank became the guy for me to use to say that. I used words I would never use: ‘I ate it up and spit it out.’ But that's the way he talked. . . When my record company caught wind of it, they were very pissed that I didn't keep it for myself. I said, ‘Hey, I can write it, but I'm not the guy to sing it.’ It was for Frank, no one else.”

9. "New York, New York” (1980)

Some people may not realize one of the most epic Frank Sinatra songs and ode to the Big Apple was originally recorded by Liza Minelli as the theme for Martin Scorsese’s 1977 film New York, New York. Though Sinatra has announced his retirement in 1971 following the release of “My Way,” he came out of retirement two years later and released this classic, penned by John Kander and Fred Ebb in 1980. “New York, New York” became Sinatra’s last Top 40 hit, and is one of his signature songs. It’s also the anthem most closely associated with the Big Apple.

10. “It had to Be You” (1980)

This jaunty hit was written by Gus Kahn and Isham Jones in 1924 shortly after Jones wife had bought him a baby grand piano and he stayed up all night working on different melodies. Then Kahn added the lyrics and a hit was born. Over the years, the song was recorded by numerous artists, including Billie Holiday, Bing Crosby, Doris Day, Tony Bennett, Ella Fitzgerald, Artie Shaw, Benny Goodman, and Barbra Streisand, but Sinatra’s version has always been a favorite. Though he began performing it in the 1940s, Sinatra didn’t record it until his 1980 album Trilogy: Past Present Future.

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Deborah Evans Price believes everyone has a story to tell and, as a journalist, she considers it a privilege to share those stories with the world. Deborah contributes to Billboard, CMA Close Up, Jesus Calling, First for Women, Woman’s World and Country Top 40 with Fitz, among other media outlets. Author of the CMA Awards Vault and Country Faith, Deborah is the 2013 winner of the Country Music Association's Media Achievement Award and the 2022 recipient of the Cindy Walker Humanitarian Award from the Academy of Western Artists. Deborah lives on a hill outside Nashville with her husband, Gary, son Trey and cat Toby.