songs The Best Frank Sinatra Songs of All Time  

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36k votes 3.1k voters 82k views 108 items Follow Embed

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

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

3
+ - 1,122 198
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Summer Wind Strangers in the Night

4
+ - 850 152
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That's Life September of My Years, That's Life

5
+ - 799 145
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Come Fly With Me A Man and His Music

6
+ - 718 162
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7
+ - 1,173 249
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My Way My Way

8
+ - 753 188
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9
+ - 629 149
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My Kind of Town A Man and His Music

10
+ - 891 116
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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
+ - 711 132
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Luck Be a Lady A Man and His Music

12
+ - 391 41
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I've Got the World on a String Songs for Young Lovers

13
+ - 638 124
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I Get a Kick Out of You Songs for Young Lovers, Masterworks The 1954-61 Albums

14
+ - 864 149
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It Was a Very Good Year September of My Years

15
+ - 619 110
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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

11 Times Frank Sinatra Was An Egomaniac Monster 16 Songs That Don't Mean What You Think They Do

16
+ - 509 130
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The Best Is Yet to Come It Might as Well Be Swing

17
+ - 529 97
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Witchcraft A Man and His Music, Sinatra's Sinatra

18
+ - 472 80
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Young at Heart Sinatra's Sinatra, Masterworks The 1954-61 Albums, Duos

19
+ - 494 92
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One for My Baby Frankly Sentimental

20
+ - 713 174
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New York, New York (thème du film) Trilogy, Strangers in the Night

21
+ - 427 83
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They Can't Take That Away From Me Songs for Young Lovers, Masterworks The 1954-61 Albums

22
+ - 486 122
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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
+ - 361 79
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All of Me Songs for Young Lovers, Swing Easy!, Masterworks The 1954-61 Albums

24
+ - 350 120
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Nice 'n Easy Nice 'n' Easy, Songs for Young Lovers, Masterworks The 1954-61 Albums

25
+ - 416 108
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Night and Day Songs for Young Lovers, A Swingin' Affair!

26
+ - 330 136
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My Funny Valentine Songs for Young Lovers, Masterworks The 1954-61 Albums

27
+ - 195 77
High Hopes is listed (or ranked) 27 on the list The Best Frank Sinatra Songs of All Time

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+ - 232 84
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Let's Fall in Love Ring-a-Ding-Ding!, Masterworks The 1954-61 Albums

29
+ - 305 98
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Come Rain or Come Shine Sinatra & Strings

The Best Frank Sinatra Albums of All Time The Worst Things To Wake Up To

30
+ - 299 95
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All or Nothing at All Sinatra & Strings

31
+ - 304 106
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Autumn Leaves Where Are You?, Songs for Young Lovers

32
+ - 218 98
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Ol' Man River The Concert Sinatra

33
+ - 286 145
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Somethin Stupid Sugar, The World We Knew

34
+ - 104 21
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Someone to Watch Over Me The Voice of Frank Sinatra

35
+ - 274 108
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Softly, as I Leave You A Man and His Music

36
+ - 281 174
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Love and Marriage A Man and His Music

37
+ - 150 76
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38
+ - 250 112
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The Second Time Around Sinatra's Sinatra

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+ - 230 104
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Stardust Sinatra & Strings

40
+ - 91 38
I'll Never Smile Again is listed (or ranked) 40 on the list The Best Frank Sinatra Songs of All Time
I'll Never Smile Again No One Cares, Songs for Young Lovers

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+ - 210 98
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Here's That Rainy Day No One Cares, Songs for Young Lovers, Masterworks The 1954-61 Albums

42
+ - 190 84
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On the Sunny Side of the Street Come Swing With Me!, Songs for Young Lovers, Masterworks The 1954-61 Albums

43
+ - 207 101
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(Love Is) The Tender Trap Sinatra-Basie: An Historic Musical First

The Best Frank Sinatra Movies The Best Stand-Up Comedy Movies on Netflix Instant

44
+ - 180 83
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Sentimental Journey Come Swing With Me!, Songs for Young Lovers, Masterworks The 1954-61 Albums

45
+ - 182 91
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Misty Sinatra & Strings

46
+ - 208 111
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You'll Never Walk Alone The Concert Sinatra

47
+ - 166 83
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Didn't We My Way

48
+ - 169 86
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Blue Moon Sinatra's Swingin' Session!!!, Songs for Young Lovers, Masterworks The 1954-61 Albums

49
+ - 158 81
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Love Is Here to Stay Songs for Young Lovers, Songs for Swingin' Lovers, Masterworks The 1954-61 Albums

50
+ - 171 95
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A Foggy Day Songs for Young Lovers, A Double Bill Presentation