Songs The Best Frank Sinatra Songs of All Time  

Voteable
Originally by
37.6k votes 3.3k voters 88.3k 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".

1
1,033 194
Ranker Video
I've Got You Under My Skin Songs for Swingin' Lovers, Songs for Young Lovers, Masterworks The 1954-61 Albums

2
1,097 216
Ranker Video
Fly Me to the Moon It Might as Well Be Swing, A Man and His Music

3
1,159 211
Ranker Video
Summer Wind Strangers in the Night

4
875 166
Ranker Video
That's Life September of My Years, That's Life

5
744 174
Ranker Video

6
830 157
Ranker Video
Come Fly With Me A Man and His Music

7
1,220 258
Ranker Video
My Way My Way

8
786 197
Ranker Video

9
646 154
Ranker Video
My Kind of Town A Man and His Music

10
933 120
Ranker Video
The Way You Look Tonight Frank Sinatra Sings Days of Wine and Roses, Moon River and Other Academy Award Winners

11
413 44
Ranker Video
SheilaBrewer added I've Got the World on a String Songs for Young Lovers

12
733 136
Ranker Video
Luck Be a Lady A Man and His Music

13
658 126
Ranker Video
I Get a Kick Out of You Songs for Young Lovers, Masterworks The 1954-61 Albums

14
890 154
Ranker Video
It Was a Very Good Year September of My Years

15
634 112
Ranker Video
All the Way Frank Sinatra Sings Days of Wine and Roses, Moon River and Other Academy Award Winners, Sinatra's Sinatra

16
527 134
Ranker Video
The Best Is Yet to Come It Might as Well Be Swing

17
548 101
Ranker Video
Witchcraft A Man and His Music, Sinatra's Sinatra

18
485 82
Ranker Video
Young at Heart Sinatra's Sinatra, Masterworks The 1954-61 Albums, Duos

19
750 177
Ranker Video
New York, New York (thème du film) Trilogy, Strangers in the Night

20
515 95
Ranker Video
JimKrantz added One for My Baby Frankly Sentimental

21
439 85
Ranker Video
They Can't Take That Away From Me Songs for Young Lovers, Masterworks The 1954-61 Albums

22
499 124
Ranker Video
In the Wee Small Hours of the Morning In the Wee Small Hours, Songs for Young Lovers, Masterworks The 1954-61 Albums

23
368 82
Ranker Video
All of Me Songs for Young Lovers, Swing Easy!, Masterworks The 1954-61 Albums

24
357 124
Ranker Video
Nice 'n Easy Nice 'n' Easy, Songs for Young Lovers, Masterworks The 1954-61 Albums

25
428 110
Ranker Video
Night and Day Songs for Young Lovers, A Swingin' Affair!

26
341 138
Ranker Video
My Funny Valentine Songs for Young Lovers, Masterworks The 1954-61 Albums

27
239 86
Ranker Video
Let's Fall in Love Ring-a-Ding-Ding!, Masterworks The 1954-61 Albums

28
312 96
Ranker Video
All or Nothing at All Sinatra & Strings

29
312 101
Ranker Video
Come Rain or Come Shine Sinatra & Strings

30
208 80
High Hopes is listed (or ranked) 30 on the list The Best Frank Sinatra Songs of All Time
JonahGiacalone added High Hopes

31
233 101
Ranker Video
Ol' Man River The Concert Sinatra

32
300 150
Ranker Video
Somethin Stupid Sugar, The World We Knew

33
309 111
Ranker Video
Autumn Leaves Where Are You?, Songs for Young Lovers

34
108 24
Ranker Video
DouglasBelardi added Someone to Watch Over Me The Voice of Frank Sinatra

35
282 112
Ranker Video
Softly, as I Leave You A Man and His Music

36
292 178
Ranker Video
Love and Marriage A Man and His Music

37
254 116
Ranker Video
The Second Time Around Sinatra's Sinatra

38
236 108
Ranker Video
Stardust Sinatra & Strings

39
97 40
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
217 102
Ranker Video
Here's That Rainy Day No One Cares, Songs for Young Lovers, Masterworks The 1954-61 Albums

41
218 104
Ranker Video
(Love Is) The Tender Trap Sinatra-Basie: An Historic Musical First

42
192 89
Ranker Video
On the Sunny Side of the Street Come Swing With Me!, Songs for Young Lovers, Masterworks The 1954-61 Albums

43
183 88
Ranker Video
Sentimental Journey Come Swing With Me!, Songs for Young Lovers, Masterworks The 1954-61 Albums

44
211 115
Ranker Video
You'll Never Walk Alone The Concert Sinatra

45
185 97
Ranker Video
Misty Sinatra & Strings

46
177 91
Ranker Video
Blue Moon Sinatra's Swingin' Session!!!, Songs for Young Lovers, Masterworks The 1954-61 Albums

47
167 84
Ranker Video
Love Is Here to Stay Songs for Young Lovers, Songs for Swingin' Lovers, Masterworks The 1954-61 Albums

48
171 88
Ranker Video
Didn't We My Way

49
158 78
Ranker Video
BobScannell added Angel Eyes

50
74 42
Learnin' the Blues is listed (or ranked) 50 on the list The Best Frank Sinatra Songs of All Time
agmla added Learnin' the Blues Sinatra-Basie: An Historic Musical First