Frank Sinatra's 20 Best Musical Moments In Film

Frank Sinatra had more than a few epic movie scenes, but among the best are of course the musical moments we all remember fondly. From dancing with Gene Kelly to singing with Shirley MacLaine, these are the most amazing numbers he ever performed during a film. Here they are in chronological order, and be sure to scroll all the way down to enter for a chance to win the Frank Sinatra & Gene Kelly DVD set [CLOSED]!  

1. "I Couldn't Sleep A Wink Last Night" (1943)

We can't get enough of this classic early Sinatra crooning with Dooley Wilson on piano.

2. "The House I Live In" (1945)

Sinatra was featured in this short film, and he won a special Academy Award and Golden Globe for patriotism. Sinatra was always great with kids.

3. "I Begged Her" (1945)

We think the many months of rehearsal were well worth it for this epic number with Gene Kelly. Sinatra definitely holds his own.

4. "If You Knew Susie" (1945)

Another of our favorites from Anchor's Aweigh. Sinatra and Kelly are hilarious in this "improvised" number.

5. "It's Gotta Come From The Heart" (1947)

Sinatra was teamed with legendary Durante, and we can't help but love his imitation.

6."Take Me Out To The Ball Game" (1949)

It doesn't get much better than the opening number to this classic film. Sinatra teamed with Gene Kelly always spelled an instant hit.

7. "The Right Girl For Me" (1949)

Another favorite from this film, is this beautiful number where Sinatra sings to Esther Williams shows off his classic crooning.

8. "You're Awful" (1949)

This silly and heartwarming number with Betty Garrett was their second time working together, and we can't help but love them as a pair.

9. "A Good Man Is Hard To Find"  (1951)

Sinatra and Winters shine in this adorable, and classic number from Meet Danny Wilson.

10. "Kisses and Tears" (1951)

We of course couldn't leave out this number with Jane Russell from the only film they did together.

11. "One For My Baby" (1954)

This is an amazing saloon number that is one of Sinatra's best signature songs.


12. "Adelaide" (1955)

Not in the original Broadway play, this song had to be created for Sinatra to expand his role - and we are certainly glad it's part of the film!

13. "The Tender Trap" (1955)

This adorable song with Debbie Reynolds marked the turning point in this romantic film. Sinatra's voice could win anybody over.

14. "Who Wants To Be A Millionaire" (1956)

The second pairing of Sinatra and Holm, this is an amazing duet from an amazing musical.

15. "Well, Did You Evah?" (1956)

Sinatra idolized Bing Crosby growing up, so we have to include their first performance together on screen. This comedic number is one of a kind.

16. "The Lady Is A Tramp" (1957)

One of Sinatra's most remembered film moments has to be this number when he's singing to Rita Hayworth.

17. "Let's Do It" (1960)

This epic number from Can-Can, pairs Sinatra with Shirley MacLaine, who he treated like a sister in real life.

18. "It's All Right With Me" (1960)

Another Can-Can classic, this is an example of a classic Sinatra ballad.

19. "Style" (1964)

Nothing beats three legends coming together for a song of epic proportions.

20. "My Kind of Town" (1964)

Finally, we had to include this song where Sinatra is truly at his best.

 The Frank Sinatra and Gene Kelly Collection DVD GIVEAWAY! [CLOSED]


To celebrate the return of Chillin' With Larry Magen, we are excited to give away this amazing boxed DVD set with 3 great musicals from two of Larry's favorite actors. The set includes classics Anchors Aweigh (1945), Take Me Out To The Ballgame (1949), and On The Town (1950). Follow the directions below for a chance to win this fantastic collection!

How to Enter

1. "Like" the Chillin' With Larry Magen and Night Owl TV Facebook Pages.

2. Enter your full name and email below for a chance to win!