17 Best Frank Sinatra Type Songs: Timeless Tracks

Hello groovy souls and beat aficionados!

We’re about to embark on a nostalgic journey through the magic of melody.

Fasten your headphones, DJs and music lovers, as we delve into the 17 best Frank Sinatra type songs. Expect crooner classics, timeless tunes, and sultry swing notes.

Let’s dive into this musical treasure trove together!

Here are the best Frank Sinatra Type Songs that you can check out:

List Of BestFrank Sinatra Type Songs

Best Frank Sinatra Type Songs in a list format:

1. “Come Fly With Me” – Frank Sinatra

One of the quintessential Sinatra songs, “Come Fly With Me” is from his 1958 album of the same name, released under Capitol Records. This upbeat song encapsulates Sinatra’s cool and charismatic aura, inviting the listener to embark on an imaginary trip around the world.

2. “I Left My Heart in San Francisco” – Tony Bennett

Released in 1962 on the album “I Left My Heart in San Francisco,” this Tony Bennett classic under Columbia Records captures a similar romantic essence. Bennett’s voice is smooth and his phrasing Sinatra-esque, paying heartfelt tribute to the city by the bay.

3. “Unforgettable” – Nat King Cole

Nat King Cole released this iconic tune on the 1951 album “Unforgettable” under Capitol Records. With his velvety voice and sentimental delivery, it feels akin to a Sinatra standard, pulling on the heartstrings in every note.

4. “Mack the Knife” – Bobby Darin

Taken from Darin’s 1959 album, “That’s All,” released by Atco Records, “Mack the Knife” showcases Bobby Darin’s powerful vocals and smooth style, reminiscent of Sinatra’s suave performances.

5. “What a Wonderful World” – Louis Armstrong

This iconic song, full of optimism and joy, is from the 1967 album “What A Wonderful World,” released by ABC Records. Armstrong’s raspy yet soothing voice evokes a Sinatra-like charm and warmth.

6. “The Lady Is a Tramp” – Ella Fitzgerald

From the 1956 album “Ella Fitzgerald Sings the Rodgers and Hart Song Book,” this Verve Records release demonstrates Ella’s charisma and swing, akin to Sinatra’s magic, as she breathes life into this classic tune.

7. “My Way” – Frank Sinatra

From the 1969 album “My Way” under Reprise Records, this song epitomizes Sinatra’s signature style – confident, emotive, and utterly captivating.

8. “Beyond the Sea” – Bobby Darin

Another Darin classic, “Beyond the Sea,” from the 1959 album “That’s All” under Atco Records, showcases the crooner’s style that’s so reminiscent of Sinatra’s own rhythm and blues.

9. “Mona Lisa” – Nat King Cole

From the 1950 album “The Nat King Cole Story” under Capitol Records, “Mona Lisa” is a classic ballad, sung with a warmth and depth that’s characteristic of Sinatra’s performances.

10. “Fly Me to the Moon” – Frank Sinatra

Released on the 1964 album “It Might As Well Be Swing” under Reprise Records, this timeless Sinatra classic literally soars with its dreamy lyrics and Sinatra’s enchanting vocals.

11. “At Last” – Etta James

Etta James’ soulful rendition of “At Last,” from the 1960 album of the same name released by Chess Records, showcases a depth of emotion that Sinatra fans will appreciate.

12. “Autumn Leaves” – Nat King Cole

This classic song from Cole’s 1956 album “Just One of Those Things” under Capitol Records is a beautiful ballad that evokes the same nostalgic atmosphere as many Sinatra classics.

13. “Night and Day” – Ella Fitzgerald

Released on the 1956 album “Ella Fitzgerald Sings the Cole Porter Song Book” under Verve Records, “Night and Day” showcases Ella’s mesmerizing voice and excellent phrasing, reminiscent of Sinatra’s own vocal mastery.

14. “Cry Me a River” – Julie London

“Cry Me a River,” from Julie London’s 1955 album “Julie Is Her Name” under Liberty Records, echoes Sinatra’s style with its heart-rending lyrics and deeply emotional delivery.

15. “Strangers in the Night” – Frank Sinatra

“Strangers in the Night,” released on the album of the same name in 1966 under Reprise Records, is another quintessential Sinatra song, capturing his unique charm and romantic allure.

16. “The Good Life” – Tony Bennett

“The Good Life,” from the 1963 album “I Wanna Be Around…” under Columbia Records, reflects the upbeat and optimistic tones often found in Sinatra’s repertoire.

17. “As Time Goes By” – Dooley Wilson

Although not a conventional crooner, Dooley Wilson’s rendition of “As Time Goes By” from the 1942 Casablanca film soundtrack, released under Warner Bros. Records, has a timeless appeal that would resonate with any Sinatra enthusiast.

Fun Facts: Top Frank Sinatra Type Tunes

“Come Fly With Me” – Frank Sinatra

This song was specially written for Sinatra by Jimmy Van Heusen and Sammy Cahn. It’s said to encapsulate the jet-set lifestyle that was just starting to become popular in the late 1950s.

“I Left My Heart in San Francisco” – Tony Bennett

Although Bennett didn’t write this song, he certainly made it famous! Interestingly, it only reached #19 on the Billboard Hot 100, yet its popularity has far outlasted many #1 hits from the same era.

“Unforgettable” – Nat King Cole

“Unforgettable” was so popular that after Cole’s death, his daughter Natalie Cole recorded a virtual duet of it with her father in 1991. The duet version won three awards at the Grammy Awards in 1992.

“Mack the Knife” – Bobby Darin

“Mack the Knife” is actually an old song from a 1928 German opera, but Bobby Darin’s swing version made it famous worldwide. His version was inducted into the Grammy Hall of Fame in 1999.

“What a Wonderful World” – Louis Armstrong

This song wasn’t initially a hit in the United States but did extremely well in the UK. Its popularity surged in the US following its inclusion in the 1987 movie “Good Morning, Vietnam.”

“The Lady Is a Tramp” – Ella Fitzgerald

Fitzgerald’s rendition of “The Lady Is a Tramp” is actually a clever commentary on the restrictive social norms of the time. She sings about being a “tramp” because she enjoys things that aren’t considered high society.

“My Way” – Frank Sinatra

While Sinatra’s rendition is the most famous, “My Way” is actually an English adaptation of a French song. Sinatra later claimed to dislike the song, despite its popularity.

“At Last” – Etta James

“At Last” was originally written for a 1941 musical film called “Orchestra Wives.” It wasn’t until Etta James recorded it nearly two decades later that it became a hit. It’s now regarded as her signature song.

“Strangers in the Night” – Frank Sinatra

“Strangers in the Night” was a major success for Sinatra, earning him two Grammy Awards. However, much like “My Way,” Sinatra confessed to not liking the song, calling it “a piece of sht” and “the worst f**ing song” he’d ever heard.

So there you have it, folks! A stellar playlist of Sinatra-esque songs, promising a timeless, smooth and enchanting musical journey.

Now, grab your headphones and let the melody magic begin!

Thanks for reading.

TBone