songs The Best Frank Sinatra Songs of All Time  

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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
1,002 186
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I've Got You Under My Skin Songs for Swingin' Lovers, Songs for Young Lovers, Masterworks The 1954-61 Albums

2
1,066 206
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Fly Me to the Moon It Might as Well Be Swing, A Man and His Music

3
1,138 204
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Summer Wind Strangers in the Night

4
859 158
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That's Life September of My Years, That's Life

5
812 149
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Come Fly With Me A Man and His Music

6
725 166
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7
1,192 253
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My Way My Way

8
766 191
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9
637 150
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My Kind of Town A Man and His Music

10
910 116
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The Way You Look Tonight Frank Sinatra Sings Days of Wine and Roses^! Moon River and Other Academy Award Winners

11
398 41
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SheilaBrewer added I've Got the World on a String Songs for Young Lovers

12
718 133
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Luck Be a Lady A Man and His Music

13
644 125
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I Get a Kick Out of You Songs for Young Lovers, Masterworks The 1954-61 Albums

14
873 150
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It Was a Very Good Year September of My Years

The Best Glen Campbell Albums of All Time

15
624 110
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All the Way Frank Sinatra Sings Days of Wine and Roses, Moon River and Other Academy Award Winners, Sinatra's Sinatra

16
515 131
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The Best Is Yet to Come It Might as Well Be Swing

17
533 98
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Witchcraft A Man and His Music, Sinatra's Sinatra

18
475 80
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Young at Heart Sinatra's Sinatra, Masterworks The 1954-61 Albums, Duos

19
502 92
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JimKrantz added One for My Baby Frankly Sentimental

20
728 175
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New York, New York (thème du film) Trilogy, Strangers in the Night

21
431 83
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They Can't Take That Away From Me Songs for Young Lovers, Masterworks The 1954-61 Albums

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22
489 122
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In the Wee Small Hours of the Morning In the Wee Small Hours, Songs for Young Lovers, Masterworks The 1954-61 Albums

23
353 120
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Nice 'n Easy Nice 'n' Easy, Songs for Young Lovers, Masterworks The 1954-61 Albums

24
361 79
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All of Me Songs for Young Lovers, Swing Easy!, Masterworks The 1954-61 Albums

25
417 109
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Night and Day Songs for Young Lovers, A Swingin' Affair!

26
333 136
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My Funny Valentine Songs for Young Lovers, Masterworks The 1954-61 Albums

27
233 84
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Let's Fall in Love Ring-a-Ding-Ding!, Masterworks The 1954-61 Albums

28
303 95
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All or Nothing at All Sinatra & Strings

11 Times Frank Sinatra Was An Egomaniac Monster

29
306 98
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Come Rain or Come Shine Sinatra & Strings

30
200 78
High Hopes is listed (or ranked) 30 on the list The Best Frank Sinatra Songs of All Time
JonahGiacalone added High Hopes

31
291 145
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Somethin Stupid Sugar, The World We Knew

32
304 108
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Autumn Leaves Where Are You?, Songs for Young Lovers

33
221 100
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Ol' Man River The Concert Sinatra

34
104 21
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DouglasBelardi added Someone to Watch Over Me The Voice of Frank Sinatra

35
275 108
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Softly, as I Leave You A Man and His Music

The 37 Greatest On-Stage Falls of All Time

36
284 176
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Love and Marriage A Man and His Music

37
250 113
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The Second Time Around Sinatra's Sinatra

38
230 105
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Stardust Sinatra & Strings

39
91 39
I'll Never Smile Again is listed (or ranked) 39 on the list The Best Frank Sinatra Songs of All Time
BobWirths added I'll Never Smile Again No One Cares, Songs for Young Lovers

40
210 99
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Here's That Rainy Day No One Cares, Songs for Young Lovers, Masterworks The 1954-61 Albums

41
190 85
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On the Sunny Side of the Street Come Swing With Me!, Songs for Young Lovers, Masterworks The 1954-61 Albums

42
210 102
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(Love Is) The Tender Trap Sinatra-Basie: An Historic Musical First

The Best Frank Sinatra Albums of All Time

43
180 84
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Sentimental Journey Come Swing With Me!, Songs for Young Lovers, Masterworks The 1954-61 Albums

44
208 111
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You'll Never Walk Alone The Concert Sinatra

45
182 92
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Misty Sinatra & Strings

46
172 87
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Blue Moon Sinatra's Swingin' Session!!!, Songs for Young Lovers, Masterworks The 1954-61 Albums

47
167 84
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Didn't We My Way

48
160 82
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Love Is Here to Stay Songs for Young Lovers, Songs for Swingin' Lovers, Masterworks The 1954-61 Albums

49
173 95
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A Foggy Day Songs for Young Lovers, A Double Bill Presentation

50
151 77
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BobScannell added Angel Eyes