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.

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list ordered by
1
645 439
Nat King Cole is listed (or ranked) 1 on the list The Greatest Crooners of All Time
Merry Christmas, The Magic of Christmas, The Nat King Cole Christmas Album
2
863 617
Frank Sinatra is listed (or ranked) 2 on the list The Greatest Crooners of All Time
Christmas With the Rat Pack, In the Wee Small Hours, Christmas Songs by Sinatra
3
799 562
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
562 308
Sammy Davis, Jr. is listed (or ranked) 4 on the list The Greatest Crooners of All Time
Christmas With the Rat Pack, Sammy & Friends, Our Shining Hour
5
385 239
Andy Williams is listed (or ranked) 5 on the list The Greatest Crooners of All Time
We Need a Little Christmas, The Andy Williams Christmas Album, Moon River
6
458 302
Tony Bennett is listed (or ranked) 6 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
7
583 412
Bing Crosby is listed (or ranked) 7 on the list The Greatest Crooners of All Time
Merry Christmas, Bing Crosby's Christmas Classics, White Christmas
8
377 249
Bobby Darin is listed (or ranked) 8 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
9
298 220
Johnny Mathis is listed (or ranked) 9 on the list The Greatest Crooners of All Time
Merry Christmas, Christmas With Johnny Mathis, A Personal Collection: The Christmas Music of Johnny Mathis
10
365 262
Perry Como is listed (or ranked) 10 on the list The Greatest Crooners of All Time
Greatest Christmas Songs, Perry Como Sings Merry Christmas Music, Christmas With Perry Como
11
314 274
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
348 250
Michael Bublé is listed (or ranked) 12 on the list The Greatest Crooners of All Time
Call Me Irresponsible, White Christmas, First Dance
13
209 165
Mel Tormé is listed (or ranked) 13 on the list The Greatest Crooners of All Time
Complete Concord Recordings, Christmas Songs, Lulu's Back In Town
14
268 182
Ray Charles is listed (or ranked) 14 on the list The Greatest Crooners of All Time
The Birth of Soul, Modern Sounds in Country and Western Music, The Spirit of Christmas
15
215 178
Harry Connick, Jr. is listed (or ranked) 15 on the list The Greatest Crooners of All Time
What a Night! A Christmas Album, When My Heart Finds Christmas, Blue Light
16
156 170
Engelbert Humperdinck is listed (or ranked) 16 on the list The Greatest Crooners of All Time
Love Rollercoaster, The Magic of Christmas, Hello Out There
17
207 159
Tom Jones is listed (or ranked) 17 on the list The Greatest Crooners of All Time
Praise & Blame, Live, She's a Lady
18
321 398
George Michael is listed (or ranked) 18 on the list The Greatest Crooners of All Time
Milla added Faith, Listen Without Prejudice, Volume 1
19
153 148
Matt Monro is listed (or ranked) 19 on the list The Greatest Crooners of All Time
Yesterdays, Matt Monro Sings, The Greatest
20
120 113
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
172 153
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
153 146
Paul Anka is listed (or ranked) 22 on the list The Greatest Crooners of All Time
Rock Swings, Three Great Guys, 32 Greatest Hits
23
102 123
Eddie Fisher is listed (or ranked) 23 on the list The Greatest Crooners of All Time
The Very Best of Eddie Fisher, I'm Yours, Games That Lovers Play
24
102 83
Jerry Vale is listed (or ranked) 24 on the list The Greatest Crooners of All Time
horseplayer added Christmas Greetings From Jerry, Jerry Vale 17 Most Requested Songs, Great Italian Hits
25
145 150
Barry Manilow is listed (or ranked) 25 on the list The Greatest Crooners of All Time