Which are Sinatra’s greatest movie songs?

Anchors Aweigh 6I’ve been trying to decide over the past week which are Sinatra’s greatest movie songs – and thought I’d pose it as a question, since there are still many of his films I haven’t seen, so I can’t come up with any definitive answers! I’d love to hear other people’s thoughts and recommendations. I found a website which has a list of all the songs he performed in films. By the look of it, this isn’t complete, since I immediately noticed that Three Coins in the Fountain was missing – presumably because he just sang it uncredited over the opening titles.

Anyway, here’s a list of five that I love at the moment, in my current order of preference, which can change from day to day. I also love all his songs in Pal Joey and All the Way in The Joker Is Wild.

5. I Fall In Love Too Easily (Anchors Aweigh, 1945): – For me this ballad by Sammy Cahn and Jule Styne is a real standout scene in Anchors Aweigh – up there with Gene Kelly’s famous dance with Jerry Mouse! Sinatra’s acting might be a little awkward at times in this film, but he really comes into his own here.

4. Guys and Dolls (Guys and Dolls, 1955): This is my favourite musical of all time – I love seeing it on stage and am also a fan of the film, despite all the controversy over Marlon Brando’s casting. Since he played Nathan Detroit rather than Sky Masterson, Sinatra didn’t get to sing some of the greatest songs in Frank Loesser’s score, including Luck Be a Lady – though he later recorded them anyway.  However, he does perform the film’s title song, together with Stubby Kaye and Johnny Silver, and also does a great job on Sue Me and Adelaide.

3. Well, Did You Evah? (High Society, 1956): As an admirer of both Sinatra and Bing Crosby, I like hearing them sing this patter song together, with its witty Cole Porter lyric and the great moment where Sinatra jokes “Don’t dig that kind of crooning, chum!”   This is another film where Sinatra missed out on the best song, True Love –  and sadly I don’t think he recorded it at all. I love Crosby’s version but would have liked to hear Sinatra’s take on this one too.

2. Three Coins in the Fountain (Three Coins in the Fountain, 1952): I must admit that I haven’t seen this film as yet, but I’m really hoping it lives up to Sinatra’s romantic crooning of the title song by Sammy Cahn and Jule Styne. It makes me want to pay a visit to Rome immediately. (I have been there once, more than 30 years ago now, but don’t remember seeing the fountain.)

1. Someone to Watch Over Me (Young at Heart, 1954): I also love the title song, but Sinatra’s performance of this Gershwin standard in a bar, with annoying customers talking and laughing over him, is even better. He has two more great torch songs in the same film, One For My Baby and Just One of Those Things.

Must also mention that I love Monique, the song by Sammy Cahn and Elmer Bernstein which never got included in Kings Go Forth (1958), as I mentioned in my previous review.


20 thoughts on “Which are Sinatra’s greatest movie songs?

  1. That’s a tough one Judy. I think I’d probably go for Well, Did You Evah? from High Society though. I think it’s a great movie and Sinatra and Crosby are clearly having a lot of fun with the song.


  2. Tough to pick Judy but here is a few…

    All the Way – The Joker is Wild
    The Lady is a Tramp – Pal Joey
    One For My Baby – Young at Heart (This film is loaded with great Sinatra songs as you mentioned aboves)
    My Kind of Town – Robin and the 7 Hoods


    • I love all of those except that I don’t remember ‘My Kind of Town’ – I wasn’t a big fan of ‘Robin and the 7 Hoods’, but do remember that it had some good songs in it, so will have to look out that particular one. Thanks, John!


  3. I think my favorite is probably “You’re Sensational” from High Society. I mean, can you imagine…Ol’ Blue Eyes singing those words to you!? Lucky Grace Kelly!

    I have only seen “Pal Joey” once (and didn’t like it), but as I recall, Frank didn’t sing “My Funny Valentine”, a lip-syncing Kim Novak did. That’s one of my favorite of his songs, so I remember being disappointed by that.


    • Patti, ‘You’re Sensational’ is a nice choice – thanks for that! And I totally agree on ‘My Funny Valentine’ – it’s one of my favourites by Sinatra too, so it’s a real shame he didn’t get to sing it in the movie. I do love his singing in ‘Pal Joey’, but would have to admit the film is a bit patchy overall compared to the same musical on stage.


  4. I love “Mind if I make Love to You” from High Society, and “It’s Allright With Me ” from Can Can.
    There are just so many to choose from. What great song writers he had, and ,boy, did he do them justice.


    • I have seen ‘Can Can’ but don’t immediately remember the one you mentioned from that film, Vienna – must give it a listen. You are so right on both counts, about the great songwriters and how well Sinatra interpreted their songs!


    • Lucy, thanks for commenting, and two great choices there. I definitely agree that ‘I Fall in Love Too Easily’ is the most real that character gets, as you say.


  5. My favorite without question is All the Way from The Joker is Wild. Then in no particular order How Deep is the Ocean & All of Me-Meet Danny Wilson, I Didn’t Know What Time It Was-Pal Joey, Time After Time-It Happened in Brooklyn.

    My absolute favorite of his songs is I’m a Fool to Want You but he never sang it in a film although he did write it with Jack Wolf and Joel Herron, it’s a beautifully intricate song so full of longing.


    • Joel, I think ‘I’m a Fool to Want You’ might just be my favourite of his too, especially the earlier recording although both versions are great. I haven’t seen ‘Meet Danny Wilson’ or ‘It Happened In Brooklyn’ yet but hope to do so soon. Definitely agree that both ‘All the Way’ and ‘I Didn’t Know What Time It Was’ are fantastic. Thanks for your thoughts on this.


  6. IIRC, “To Love And Be Loved” wasn’t sung by Sinatra as part of the movie “Some Came Running,” but it’s a brilliant recording by Frank from his later years at Capitol.


    • Vincent, you remember right – I watched this film very recently and reviewed it here, and was surprised to discover that this great song was only performed by Shirley MacLaine, not by either Sinatra or Dean Martin! I definitely agree that Sinatra’s recording of it is brilliant, all the same. Thanks for the comment!


  7. Well Judy, on this occasion you have issued quite an interesting as well as a difficult challenge; one that I have shared with my wife, as we both appreciate Sinatra’s talent. In our opinion Sinatra’s voice was at its peak in the 1950’s to the mid 1960’s” , so our choices extend over this period. Nevertheless, we still could not limit the number to 5 – however hard we tried.

    (6) “The Lady Is a Tramp” from “Pal Joey”(1957)
    “Sandwiched” between the “top billed”, a more mature, but still interesting Rita Hayworth and the beautiful Kim Novak, Sinatra appeared to be very comfortable. With a soundtrack that included “There’s a Small Hotel”; “I Could Write a Book”; “I Didn’t Know What Time It Was”; and “Bewitched, Bothered and Bewildered”, (in the dream sequence), the choice proved to be a difficult one, but “Lady” finally won out!

    (5) “All The Way” from “The Joker Is Wild” (1957)
    A very good year for Sinatra fans and one of the most popular songs of the year solved our problem .

    (4) “Your Brought A New Kind Of Love To Me” from “A New Kind Of Love” (1963)
    Sung on the soundtrack of the Paul Newman and Joanne Woodward film. Sinatra’s swinging version of the song, in our opinion was the best part of a disappointing film.

    (3) ” It’s All Right By Me” from “Can-Can” (1960)
    ” C’est Magnifique” and other great Cole Porter “standards” are “pipped at the post” by the superbly restrained and emotive rendition of this song by Sinatra, in the film.

    (2) “All My Tomorrows” from “A Hole In The Head” (1959)
    Sinatra stars in this film with a host of talented supporting actors including Edward G. Robinson; he sings this song over the opening credits and it is a sentimental favourite of my own.

    (1) “Well, Did You Evah!” from “High Society” ( 1956)
    No true fan of “Swing/Jazz’, could resist any film that combines the talents of such musical legends as Louis Armstrong, Bing Crosby and the “Chairman of the Board”, himself. Sinatra’s versions of “Your Sensational”, “Mind If I Make Love To You”, and his duet with the talented Celeste Holm, “Who Wants To Be A Millionaire” are only surpassed by the Crosby/Sinatra classic, “Well, Did You Evah!”

    Judy, We really enjoyed the exercise; thank you for your challenge


    • Rod, I must be the one to thank both you and your wife – both for this great list and for the thoughts you have included with each one. I don’t yet know ‘All My Tomorrows’ or ‘You Brought a New Kind of Love to Me’, so will make sure I give them both a listen as soon as possible.

      I agree with you on the superb line-up of songs in ‘Pal Joey’ and ‘High Society’ – I wasn’t quite such a fan of ‘Can Can’, but did like the songs you have picked out here and will listen to them again soon. Thanks again!


  8. Pingback: Which is Frank Sinatra’s best film performance as an actor? | Movie classics

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