Songs The Best Frank Sinatra Songs of All Time  

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37.7k votes 3.3k voters 88.6k 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
1,035 196
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Songs for Swingin' Lovers, Songs for Young Lovers, Masterworks The 1954-61 Albums

2
1,102 217
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It Might as Well Be Swing, A Man and His Music

3
1,162 212
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Strangers in the Night

4
878 166
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September of My Years, That's Life

5
747 174
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6
833 157
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A Man and His Music

7
1,225 259
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My Way

8
791 197
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9
648 154
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A Man and His Music

10
936 120
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Frank Sinatra Sings Days of Wine and Roses, Moon River and Other Academy Award Winners

11
415 44
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SheilaBrewer added Songs for Young Lovers

12
736 137
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A Man and His Music

13
661 126
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Songs for Young Lovers, Masterworks The 1954-61 Albums

14
893 154
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September of My Years

15
635 112
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Frank Sinatra Sings Days of Wine and Roses, Moon River and Other Academy Award Winners, Sinatra's Sinatra

16
529 135
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It Might as Well Be Swing

17
549 101
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A Man and His Music, Sinatra's Sinatra

18
485 83
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Sinatra's Sinatra, Masterworks The 1954-61 Albums, Duos

19
753 177
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Trilogy, Strangers in the Night

20
516 95
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JimKrantz added Frankly Sentimental

21
441 85
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Songs for Young Lovers, Masterworks The 1954-61 Albums

22
502 124
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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
430 110
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Songs for Young Lovers, A Swingin' Affair!

26
344 138
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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
314 101
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Sinatra & Strings

30
209 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
302 150
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Sugar, The World We Knew

33
311 111
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Where Are You?, Songs for Young Lovers

34
109 24
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DouglasBelardi added The Voice of Frank Sinatra

35
282 112
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A Man and His Music

36
293 179
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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
217 102
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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
183 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
179 91
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Sinatra's Swingin' Session!!!, Songs for Young Lovers, Masterworks The 1954-61 Albums

46
185 97
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Sinatra & Strings

47
168 84
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Songs for Young Lovers, Songs for Swingin' Lovers, Masterworks The 1954-61 Albums

48
171 88
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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