Best Frank Sinatra Songs: 20 Timeless Hits

Frank Sinatra is one of the biggest music superstars ever, and one of the best singers in recorded history. The man, the legend, the style, the voice. Frank is the perfect image of class and sophistication in music. I’ve been a fan for as long as I can remember. So when it came time to create the chart of his greatest hits, I took it very seriously.

These are the Best Frank Sinatra songs, hand picked from his entire catalog. If you want to enjoy the most iconic, classy, timeless tracks from one of the greatest singers of all times, this is THE list.

As always, I’ve included both YouTube and Spotify players alongside the song list, so you can easily enjoy all the music right here.

Best Frank Sinatra Songs

These are some of the best Frank Sinatra masterpieces. Not just the most popular ones, because popularity is nowadays often determined by soulless metrics and random coincidence that really don’t reflect the true value of a song. These are the songs that actually showcase Frank’s uniqueness and greatness.

🎧 Top 20 Greatest Frank Sinatra Songs:

1. Autumn Leaves
2. Come Fly With Me
3. One For My Baby
4. Fly Me To The Moon
5. I’m a Fool to Want You
6. That’s Life
7. It Was A Very Good Year
8. Nice ‘n’ Easy
9. Strangers In The Night
10. Somethin’ Stupid
11. My Way
12. My Funny Valentine
13. Theme From New York, New York
14. Let It Snow! Let It Snow! Let It Snow!
15. The Best Is Yet To Come
16. In The Wee Small Hours Of The Morning
17. Glad To Be Unhappy
18. I’ve Got The World On A String
19. I’ll Never Smile Again
20. It Happened In Monterey

Listen to the playlist on my Spotify:

Or enjoy them via my YouTube playlist. Simply hit the ‘Play’ button and the music will start.

Frank Sinatra Greatest Albums

Choosing the best Frank Sinatra album is more than tricky. Firsts of all because he had almost 59 albums, that’s A LOT of songs to pick from. And secondly because it very much depends on personal taste, as well as on your current mood. Do you want emotional, soft and deep music? Or do you feel like listening to joyful upbeat tunes?

But regardless of those factors, these are some his most universally acclaimed albums: “In the Wee Small Hours” (1955), “Come Fly with Me” (1958), “Only the Lonely” (1958), “Songs for Swingin’ Lovers!” (1956), and “Where Are You?” (1957).

More About Frank

Because Frank is such an iconic figure his biography is well researched and covered. So instead of repeating it here, I though I’d share less know facts about Sinatra.

Did you know that he was a man of many talents and surprising qualities outside of music? For example, he won an Academy Award for his acting (Oscar for Best Supporting Actor in the 1953 movie From Here to Eternity). He was also a big fan of Italian cooking, preferring simple dishes like spaghetti with marinara sauce.

Or did you know that Sinatra often recorded songs in a single take? He wanted to keep the performance as authentic and full of emotion as possible.

Being super famous he knew very well the cost of privacy and its value. So he liked to spend downtime with close friends and relax at his home in Palm Springs.

For more stories about Frank check the official website.