songs The Best Frank Sinatra Songs of All Time  

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37k votes 3.3k voters 87.4k 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
1,022 190
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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
1,086 211
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Fly Me to the Moon It Might as Well Be Swing, A Man and His Music

3
1,150 207
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Summer Wind Strangers in the Night

4
868 162
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That's Life September of My Years, That's Life

5
823 152
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Come Fly With Me A Man and His Music

6
736 171
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7
1,208 253
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My Way My Way

8
775 193
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9
643 151
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My Kind of Town A Man and His Music

10
924 118
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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
408 41
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SheilaBrewer added I've Got the World on a String Songs for Young Lovers

12
725 134
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Luck Be a Lady A Man and His Music

13
650 125
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I Get a Kick Out of You Songs for Young Lovers, Masterworks The 1954-61 Albums

14
882 151
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It Was a Very Good Year September of My Years

The Best Glen Campbell Albums of All Time

15
628 110
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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
522 132
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The Best Is Yet to Come It Might as Well Be Swing

17
544 98
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Witchcraft A Man and His Music, Sinatra's Sinatra

18
482 80
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Young at Heart Sinatra's Sinatra, Masterworks The 1954-61 Albums, Duos

19
509 92
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JimKrantz added One for My Baby Frankly Sentimental

20
739 176
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New York, New York (thème du film) Trilogy, Strangers in the Night

21
435 83
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They Can't Take That Away From Me Songs for Young Lovers, Masterworks The 1954-61 Albums

The Greatest Chick Rock Bands Ever

22
494 123
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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
366 79
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All of Me Songs for Young Lovers, Swing Easy!, Masterworks The 1954-61 Albums

24
355 122
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Nice 'n Easy Nice 'n' Easy, Songs for Young Lovers, Masterworks The 1954-61 Albums

25
421 110
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Night and Day Songs for Young Lovers, A Swingin' Affair!

26
335 138
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My Funny Valentine Songs for Young Lovers, Masterworks The 1954-61 Albums

27
237 84
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Let's Fall in Love Ring-a-Ding-Ding!, Masterworks The 1954-61 Albums

28
305 96
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All or Nothing at All Sinatra & Strings

Fascinating Stories About Frank Sinatra's Personal Life

29
308 99
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Come Rain or Come Shine Sinatra & Strings

30
205 78
High Hopes is listed (or ranked) 30 on the list The Best Frank Sinatra Songs of All Time
JonahGiacalone added High Hopes

31
227 101
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Ol' Man River The Concert Sinatra

32
294 147
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Somethin Stupid Sugar, The World We Knew

33
107 21
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DouglasBelardi added Someone to Watch Over Me The Voice of Frank Sinatra

34
306 110
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Autumn Leaves Where Are You?, Songs for Young Lovers

35
277 110
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Softly, as I Leave You A Man and His Music

The Greatest Songs by '90s One-Hit Wonders

36
288 177
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Love and Marriage A Man and His Music

37
251 115
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The Second Time Around Sinatra's Sinatra

38
232 107
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Stardust Sinatra & Strings

39
94 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
213 100
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Here's That Rainy Day No One Cares, Songs for Young Lovers, Masterworks The 1954-61 Albums

41
214 103
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(Love Is) The Tender Trap Sinatra-Basie: An Historic Musical First

42
191 87
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On the Sunny Side of the Street Come Swing With Me!, Songs for Young Lovers, Masterworks The 1954-61 Albums

The Most Underrated Frank Sinatra Songs

43
181 86
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Sentimental Journey Come Swing With Me!, Songs for Young Lovers, Masterworks The 1954-61 Albums

44
209 113
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You'll Never Walk Alone The Concert Sinatra

45
183 95
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Misty Sinatra & Strings

46
175 89
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Blue Moon Sinatra's Swingin' Session!!!, Songs for Young Lovers, Masterworks The 1954-61 Albums

47
170 86
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Didn't We My Way

48
164 82
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Love Is Here to Stay Songs for Young Lovers, Songs for Swingin' Lovers, Masterworks The 1954-61 Albums

49
72 40
Learnin' the Blues is listed (or ranked) 49 on the list The Best Frank Sinatra Songs of All Time
agmla added Learnin' the Blues Sinatra-Basie: An Historic Musical First

50
155 78
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BobScannell added Angel Eyes