Music

The Best Frank Sinatra Songs of All Time 

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Updated July 13, 2020 40.1k votes 3.6k voters 94.7k views 110 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
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Strangers in the Night
2
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My Way
3
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Songs for Swingin' Lovers, Songs for Young Lovers, Masterworks The 1954-61 Albums
4
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It Might as Well Be Swing, A Man and His Music
5
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September of My Years, That's Life
6
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Frank Sinatra Sings Days of Wine and Roses, Moon River and Other Academy Award Winners
7
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Trilogy, Strangers in the Night
8
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9
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10
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A Man and His Music
11
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Songs for Young Lovers, Masterworks The 1954-61 Albums
12
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It Might as Well Be Swing
13
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JimKrantz added Frankly Sentimental
14
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A Man and His Music
15
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Sinatra's Sinatra, Masterworks The 1954-61 Albums, Duos
16
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Nice 'n' Easy, Songs for Young Lovers, Masterworks The 1954-61 Albums
17
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Songs for Young Lovers, Masterworks The 1954-61 Albums
18
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Ring-a-Ding-Ding!, Masterworks The 1954-61 Albums
19
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Sugar, The World We Knew
20
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The Concert Sinatra
21
High Hopes is listed (or ranked) 21 on the list The Best Frank Sinatra Songs of All Time
JonahGiacalone added
22
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September of My Years
23
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A Man and His Music
24
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Frank Sinatra Sings Days of Wine and Roses, Moon River and Other Academy Award Winners, Sinatra's Sinatra
25
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A Man and His Music, Sinatra's Sinatra