songs The Best Frank Sinatra Songs of All Time  

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37.2k votes 3.3k voters 87.7k 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".

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1,024 190
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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
1,089 212
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Fly Me to the Moon It Might as Well Be Swing, A Man and His Music

3
1,153 207
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Summer Wind Strangers in the Night

4
870 162
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That's Life September of My Years, That's Life

5
825 152
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Come Fly With Me A Man and His Music

6
738 171
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7
1,211 253
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My Way My Way

8
777 193
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9
644 151
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My Kind of Town A Man and His Music

10
927 118
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The Way You Look Tonight Frank Sinatra Sings Days of Wine and Roses, Moon River and Other Academy Award Winners

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411 41
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SheilaBrewer added I've Got the World on a String Songs for Young Lovers

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727 134
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Luck Be a Lady A Man and His Music

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652 125
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I Get a Kick Out of You Songs for Young Lovers, Masterworks The 1954-61 Albums

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885 151
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It Was a Very Good Year September of My Years

The Best Glen Campbell Albums of All Time

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629 110
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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

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524 132
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The Best Is Yet to Come It Might as Well Be Swing

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545 98
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Witchcraft A Man and His Music, Sinatra's Sinatra

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483 80
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Young at Heart Sinatra's Sinatra, Masterworks The 1954-61 Albums, Duos

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511 92
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JimKrantz added One for My Baby Frankly Sentimental

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741 176
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New York, New York (thème du film) Trilogy, Strangers in the Night

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436 83
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They Can't Take That Away From Me Songs for Young Lovers, Masterworks The 1954-61 Albums

The Best Music Apps

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495 123
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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

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367 79
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All of Me Songs for Young Lovers, Swing Easy!, Masterworks The 1954-61 Albums

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356 122
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Nice 'n Easy Nice 'n' Easy, Songs for Young Lovers, Masterworks The 1954-61 Albums

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422 110
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Night and Day Songs for Young Lovers, A Swingin' Affair!

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336 138
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My Funny Valentine Songs for Young Lovers, Masterworks The 1954-61 Albums

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238 84
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Let's Fall in Love Ring-a-Ding-Ding!, Masterworks The 1954-61 Albums

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307 96
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All or Nothing at All Sinatra & Strings

Fascinating Stories About Frank Sinatra's Personal Life

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206 78
High Hopes is listed (or ranked) 29 on the list The Best Frank Sinatra Songs of All Time
JonahGiacalone added High Hopes

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309 99
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Come Rain or Come Shine Sinatra & Strings

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229 101
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Ol' Man River The Concert Sinatra

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294 148
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Somethin Stupid Sugar, The World We Knew

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307 110
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Autumn Leaves Where Are You?, Songs for Young Lovers

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107 22
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DouglasBelardi added Someone to Watch Over Me The Voice of Frank Sinatra

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278 111
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Softly, as I Leave You A Man and His Music

16 Songs That Don't Mean What You Think They Do

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289 177
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Love and Marriage A Man and His Music

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252 115
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The Second Time Around Sinatra's Sinatra

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233 107
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Stardust Sinatra & Strings

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95 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

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213 101
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Here's That Rainy Day No One Cares, Songs for Young Lovers, Masterworks The 1954-61 Albums

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192 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

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214 104
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(Love Is) The Tender Trap Sinatra-Basie: An Historic Musical First

The Most Underrated Frank Sinatra Songs

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182 86
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Sentimental Journey Come Swing With Me!, Songs for Young Lovers, Masterworks The 1954-61 Albums

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210 113
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You'll Never Walk Alone The Concert Sinatra

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184 95
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Misty Sinatra & Strings

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176 89
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Blue Moon Sinatra's Swingin' Session!!!, Songs for Young Lovers, Masterworks The 1954-61 Albums

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171 86
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Didn't We My Way

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165 82
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Love Is Here to Stay Songs for Young Lovers, Songs for Swingin' Lovers, Masterworks The 1954-61 Albums

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73 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

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156 78
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BobScannell added Angel Eyes