Singers The Greatest Crooners of All Time  

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Who are the greatest crooners of all time? This list of crooners includes many of the greatest male singers ever, in any genre, and there are some modern day, popular crooners included as well. Put simply, a crooner is a singer, typically male, who sings softly, slowly, and, often, sentimentally. Some of the best crooners of all time were masters of jazz standards. Crooning certainly emphasizes strong vocals.

Picture a huge, smoky ballroom full of people swaying to the music, as crooner singers stand on the stage, serenading them with the standards – many with themes of lost love, found love and other heartfelt sentiments. Romantic? You bet. “Croon” does rhyme with “swoon,” after all.  If you’re a fan, you’ll likely find your favorite crooners listed here – but you may also find some new favorites to check out.

Back in the day - and by “day” this means the 1930s, '40s, and '50s, good crooners were a staple of popular music. By the mid-1960s, crooning had lost a bit of its luster. It is by no means dead, however. While many of the top crooners are no longer with us (Frank Sinatra, Bing Crosby, Dean Martin), some still are: Tony Bennett still tours, as does Johnny Mathis. And there are plenty of new modern-era crooners available for you to discover. Harry Connick, Jr., Michael Buble, and Michael Feinstein are all contemporary crooners, putting their own, unique spin on the classics.

Are these the greatest crooners ever? You decide, with your votes. Vote for the best crooners of all time, and let’s see who comes out on top.

list ordered by

1
705 489
Frank Sinatra is listed (or ranked) 1 on the list The Greatest Crooners of All Time
Christmas With the Rat Pack, In the Wee Small Hours, Christmas Songs by Sinatra

2
423 207
Sammy Davis, Jr. is listed (or ranked) 2 on the list The Greatest Crooners of All Time
Christmas With the Rat Pack, Sammy & Friends, Our Shining Hour

3
655 447
Dean Martin is listed (or ranked) 3 on the list The Greatest Crooners of All Time
Christmas With the Rat Pack, Dino / You're the Best Thing That Ever Happened to Me, A Winter Romance

4
523 350
Nat King Cole is listed (or ranked) 4 on the list The Greatest Crooners of All Time
Merry Christmas, The Magic of Christmas, The Nat King Cole Christmas Album

5
512 345
Bing Crosby is listed (or ranked) 5 on the list The Greatest Crooners of All Time
Merry Christmas, Bing Crosby's Christmas Classics, White Christmas

6
306 210
Andy Williams is listed (or ranked) 6 on the list The Greatest Crooners of All Time
We Need a Little Christmas, The Andy Williams Christmas Album, Moon River

7
377 276
Tony Bennett is listed (or ranked) 7 on the list The Greatest Crooners of All Time
Snowfall: The Tony Bennett Christmas Album, I Left My Heart in San Francisco, A Swingin' Christmas

8
254 197
Johnny Mathis is listed (or ranked) 8 on the list The Greatest Crooners of All Time
Merry Christmas, Christmas With Johnny Mathis, A Personal Collection: The Christmas Music of Johnny Mathis

9
327 237
Perry Como is listed (or ranked) 9 on the list The Greatest Crooners of All Time
Greatest Christmas Songs, Perry Como Sings Merry Christmas Music, Christmas With Perry Como

10
306 225
Bobby Darin is listed (or ranked) 10 on the list The Greatest Crooners of All Time
Beyond the Sea: The Very Best of Bobby Darin, You're the Reason I'm Living / I Wanna Be Around, Bobby Darin Sings Doctor Doolitle / Born Walden Robert Cassotto

11
277 252
Louis Armstrong is listed (or ranked) 11 on the list The Greatest Crooners of All Time
Hot Fives and Hot Sevens, American Freedom, C'est si bon

12
191 137
Mel Tormé is listed (or ranked) 12 on the list The Greatest Crooners of All Time
Complete Concord Recordings, Christmas Songs, Lulu's Back In Town

13
293 218
Michael Bublé is listed (or ranked) 13 on the list The Greatest Crooners of All Time
Call Me Irresponsible, White Christmas, First Dance

14
185 156
Harry Connick, Jr. is listed (or ranked) 14 on the list The Greatest Crooners of All Time
What a Night! A Christmas Album, When My Heart Finds Christmas, Blue Light

15
232 169
Ray Charles is listed (or ranked) 15 on the list The Greatest Crooners of All Time
The Birth of Soul, Modern Sounds in Country and Western Music, The Spirit of Christmas

16
301 365
George Michael is listed (or ranked) 16 on the list The Greatest Crooners of All Time
Milla added Faith, Listen Without Prejudice, Volume 1

17
134 154
Engelbert Humperdinck is listed (or ranked) 17 on the list The Greatest Crooners of All Time
Love Rollercoaster, The Magic of Christmas, Hello Out There

18
181 149
Tom Jones is listed (or ranked) 18 on the list The Greatest Crooners of All Time
Praise & Blame, Live, She's a Lady

19
130 137
Matt Monro is listed (or ranked) 19 on the list The Greatest Crooners of All Time
Yesterdays, Matt Monro Sings, The Greatest

20
97 101
Robert Goulet is listed (or ranked) 20 on the list The Greatest Crooners of All Time
Camelot (1960 original Broadway cast), 16 Most Requested Songs, Greatest Hits

21
154 137
Fred Astaire is listed (or ranked) 21 on the list The Greatest Crooners of All Time
"Nice Work": Fred Astaire Sings Gershwin, They Can't Take That Away From Me / Beginner's Luck, The Complete London Sessions

22
92 106
Eddie Fisher is listed (or ranked) 22 on the list The Greatest Crooners of All Time
The Very Best of Eddie Fisher, I'm Yours, Games That Lovers Play

23
82 72
Jerry Vale is listed (or ranked) 23 on the list The Greatest Crooners of All Time
horseplayer added Christmas Greetings From Jerry, Jerry Vale 17 Most Requested Songs, Great Italian Hits

24
123 136
Paul Anka is listed (or ranked) 24 on the list The Greatest Crooners of All Time
Rock Swings, Three Great Guys, 32 Greatest Hits

25
120 133
Barry Manilow is listed (or ranked) 25 on the list The Greatest Crooners of All Time