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
990 177
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I've Got You Under My Skin Songs for Swingin' Lovers, Songs for Young Lovers, Masterworks The 1954-61 Albums

The Best Glen Campbell Albums of All Time The Best Wineries in France

2
1,054 199
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Fly Me to the Moon It Might as Well Be Swing, A Man and His Music

3
1,128 199
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Summer Wind Strangers in the Night

4
854 153
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That's Life September of My Years, That's Life

5
721 162
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6
804 147
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Come Fly With Me A Man and His Music

7
1,180 250
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My Way My Way

8
758 189
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9
632 149
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My Kind of Town A Man and His Music

10
896 116
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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
713 132
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Luck Be a Lady A Man and His Music

12
394 41
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SheilaBrewer added I've Got the World on a String Songs for Young Lovers

13
640 124
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I Get a Kick Out of You Songs for Young Lovers, Masterworks The 1954-61 Albums

14
866 149
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It Was a Very Good Year September of My Years

15
621 110
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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 Catchiest Viral Internet Songs of All Time

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

17
530 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
497 92
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JimKrantz added One for My Baby Frankly Sentimental

20
718 174
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New York, New York (thème du film) Trilogy, Strangers in the Night

21
428 83
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They Can't Take That Away From Me Songs for Young Lovers, Masterworks The 1954-61 Albums

22
487 122
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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
351 120
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Nice 'n Easy Nice 'n' Easy, Songs for Young Lovers, Masterworks The 1954-61 Albums

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

26
196 77
High Hopes is listed (or ranked) 26 on the list The Best Frank Sinatra Songs of All Time
JonahGiacalone added High Hopes

27
330 136
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My Funny Valentine Songs for Young Lovers, Masterworks The 1954-61 Albums

28
232 84
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Let's Fall in Love Ring-a-Ding-Ding!, Masterworks The 1954-61 Albums

29
301 95
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All or Nothing at All Sinatra & Strings

The Best Frank Sinatra Albums of All Time Girls Reveal What They Actually Want for Valentine's Day

30
305 98
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Come Rain or Come Shine Sinatra & Strings

31
304 107
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Autumn Leaves Where Are You?, Songs for Young Lovers

32
287 145
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Somethin Stupid Sugar, The World We Knew

33
219 99
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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

36
281 174
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Love and Marriage A Man and His Music

37
150 77
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BobScannell added Angel Eyes

38
250 113
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The Second Time Around Sinatra's Sinatra

39
230 105
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Stardust Sinatra & Strings

40
91 39
I'll Never Smile Again is listed (or ranked) 40 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

41
210 99
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Here's That Rainy Day No One Cares, Songs for Young Lovers, Masterworks The 1954-61 Albums

42
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

43
207 102
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(Love Is) The Tender Trap Sinatra-Basie: An Historic Musical First

The Best Frank Sinatra Movies The Best Restaurants at LAX

44
180 84
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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 84
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Didn't We My Way

48
169 87
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Blue Moon Sinatra's Swingin' Session!!!, Songs for Young Lovers, Masterworks The 1954-61 Albums

49
158 82
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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