Songs The Best Frank Sinatra Songs of All Time  

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37.9k votes 3.4k voters 89.5k 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
1,046 199
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Songs for Swingin' Lovers, Songs for Young Lovers, Masterworks The 1954-61 Albums

2
1,111 221
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It Might as Well Be Swing, A Man and His Music

3
1,170 213
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Strangers in the Night

4
885 168
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September of My Years, That's Life

5
751 175
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6
835 162
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A Man and His Music

7
1,237 261
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My Way

8
798 198
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9
648 159
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A Man and His Music

10
945 121
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Frank Sinatra Sings Days of Wine and Roses, Moon River and Other Academy Award Winners

11
738 138
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A Man and His Music

12
416 46
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SheilaBrewer added Songs for Young Lovers

13
665 126
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Songs for Young Lovers, Masterworks The 1954-61 Albums

14
897 156
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September of My Years

15
640 112
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Frank Sinatra Sings Days of Wine and Roses, Moon River and Other Academy Award Winners, Sinatra's Sinatra

16
531 135
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It Might as Well Be Swing

17
551 101
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A Man and His Music, Sinatra's Sinatra

18
488 83
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Sinatra's Sinatra, Masterworks The 1954-61 Albums, Duos

19
760 177
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Trilogy, Strangers in the Night

20
517 98
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JimKrantz added Frankly Sentimental

21
445 85
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Songs for Young Lovers, Masterworks The 1954-61 Albums

22
503 124
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In the Wee Small Hours, Songs for Young Lovers, Masterworks The 1954-61 Albums

23
370 82
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Songs for Young Lovers, Swing Easy!, Masterworks The 1954-61 Albums

24
359 124
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Nice 'n' Easy, Songs for Young Lovers, Masterworks The 1954-61 Albums

25
431 110
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Songs for Young Lovers, A Swingin' Affair!

26
346 138
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Songs for Young Lovers, Masterworks The 1954-61 Albums

27
241 86
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Ring-a-Ding-Ding!, Masterworks The 1954-61 Albums

28
314 96
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Sinatra & Strings

29
318 101
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Sinatra & Strings

30
210 80
High Hopes is listed (or ranked) 30 on the list The Best Frank Sinatra Songs of All Time
JonahGiacalone added

31
235 101
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The Concert Sinatra

32
307 151
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Sugar, The World We Knew

33
312 111
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Where Are You?, Songs for Young Lovers

34
111 24
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DouglasBelardi added The Voice of Frank Sinatra

35
282 113
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A Man and His Music

36
295 179
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A Man and His Music

37
254 116
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Sinatra's Sinatra

38
237 108
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Sinatra & Strings

39
97 40
I'll Never Smile Again is listed (or ranked) 39 on the list The Best Frank Sinatra Songs of All Time
BobWirths added No One Cares, Songs for Young Lovers

40
219 102
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No One Cares, Songs for Young Lovers, Masterworks The 1954-61 Albums

41
219 104
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Sinatra-Basie: An Historic Musical First

42
193 89
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Come Swing With Me!, Songs for Young Lovers, Masterworks The 1954-61 Albums

43
184 88
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Come Swing With Me!, Songs for Young Lovers, Masterworks The 1954-61 Albums

44
212 115
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The Concert Sinatra

45
180 91
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Sinatra's Swingin' Session!!!, Songs for Young Lovers, Masterworks The 1954-61 Albums

46
170 84
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Songs for Young Lovers, Songs for Swingin' Lovers, Masterworks The 1954-61 Albums

47
185 98
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Sinatra & Strings

48
171 89
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My Way

49
158 78
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BobScannell added

50
74 42
Learnin' the Blues is listed (or ranked) 50 on the list The Best Frank Sinatra Songs of All Time
agmla added Sinatra-Basie: An Historic Musical First