Songs The Best Frank Sinatra Songs of All Time  

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38.3k votes 3.4k voters 89.8k 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.

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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
1,051 202
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Songs for Swingin' Lovers, Songs for Young Lovers, Masterworks The 1954-61 Albums

2
1,118 223
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It Might as Well Be Swing, A Man and His Music

3
1,176 213
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Strangers in the Night

4
890 169
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September of My Years, That's Life

5
756 176
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6
840 164
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A Man and His Music

7
1,244 261
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My Way

8
805 198
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9
652 163
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A Man and His Music

10
953 121
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Frank Sinatra Sings Days of Wine and Roses, Moon River and Other Academy Award Winners

11
741 140
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A Man and His Music

12
419 47
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SheilaBrewer added Songs for Young Lovers

13
671 126
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Songs for Young Lovers, Masterworks The 1954-61 Albums

14
903 156
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September of My Years

15
645 112
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Frank Sinatra Sings Days of Wine and Roses, Moon River and Other Academy Award Winners, Sinatra's Sinatra

16
534 136
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It Might as Well Be Swing

17
555 101
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A Man and His Music, Sinatra's Sinatra

18
494 83
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Sinatra's Sinatra, Masterworks The 1954-61 Albums, Duos

19
765 178
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Trilogy, Strangers in the Night

20
521 99
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JimKrantz added Frankly Sentimental

21
449 85
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Songs for Young Lovers, Masterworks The 1954-61 Albums

22
507 125
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In the Wee Small Hours, Songs for Young Lovers, Masterworks The 1954-61 Albums

23
374 82
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Songs for Young Lovers, Swing Easy!, Masterworks The 1954-61 Albums

24
362 125
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Nice 'n' Easy, Songs for Young Lovers, Masterworks The 1954-61 Albums

25
435 112
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Songs for Young Lovers, A Swingin' Affair!