Songs The Best Frank Sinatra Songs of All Time  

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38.4k votes 3.4k voters 90k views 113 items

List Rules Vote for the top Sinatra songs (in your humble opinion). His discography is huge, so add your favorites to the list if they're missing.

List of the best Frank Sinatra songs, as voted on by fans like you. Widely regarded as one of the best singers of all time, Frank Sinatra enjoyed a long and lustrous career in the music industry that spanned nearly 50 years. Getting his start as a young boy in the swing era, Sinatra went on to sell a record breaking 150 million albums worldwide in his adult years. With just shy of 60 studio albums released, it's certainly not easy deciding what the top Sinatra songs are. We want you to vote for the songs you love, but we also want you to add your favorites that we didn't include. Are you partial to Frank's Columbia period songs? What about his work while with Capitol or Reprise? The amazing thing about Sinatra is that he only got better as the years went on.

We've included audio of each track on this page with help from YouTube, so be sure to listen to these tracks and relive the glory of Sinatra while you're voting. Absolute classic Sinatra hits like "Luck Be A Lady" and "Fly Me To The Moon" are here, but we've also included lesser known gems like "Witchcraft," "The Lady Is A Tramp," and "Here's That Rainy Day".
list ordered by

1
1,053 202
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Songs for Swingin' Lovers, Songs for Young Lovers, Masterworks The 1954-61 Albums

2
1,121 224
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It Might as Well Be Swing, A Man and His Music

3
1,177 214
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Strangers in the Night

4
891 170
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September of My Years, That's Life

5
757 176
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6
842 164
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A Man and His Music

7
1,248 261
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My Way

8
806 199
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9
653 163
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A Man and His Music

10
954 122
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Frank Sinatra Sings Days of Wine and Roses, Moon River and Other Academy Award Winners

11
421 47
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SheilaBrewer added Songs for Young Lovers

12
741 141
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A Man and His Music

13
672 126
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Songs for Young Lovers, Masterworks The 1954-61 Albums

14
904 157
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September of My Years

15
646 112
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Frank Sinatra Sings Days of Wine and Roses, Moon River and Other Academy Award Winners, Sinatra's Sinatra

16
534 137
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It Might as Well Be Swing

17
556 101
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A Man and His Music, Sinatra's Sinatra

18
495 83
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Sinatra's Sinatra, Masterworks The 1954-61 Albums, Duos

19
767 178
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Trilogy, Strangers in the Night

20
522 99
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JimKrantz added Frankly Sentimental

21
450 85
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Songs for Young Lovers, Masterworks The 1954-61 Albums

22
507 126
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In the Wee Small Hours, Songs for Young Lovers, Masterworks The 1954-61 Albums

23
375 82
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Songs for Young Lovers, Swing Easy!, Masterworks The 1954-61 Albums

24
363 125
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Nice 'n' Easy, Songs for Young Lovers, Masterworks The 1954-61 Albums

25
436 112
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Songs for Young Lovers, A Swingin' Affair!