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
569 280
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
515 246
Dean Martin is listed (or ranked) 2 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

3
419 218
Nat King Cole is listed (or ranked) 3 on the list The Greatest Crooners of All Time
Merry Christmas, The Magic of Christmas, The Nat King Cole Christmas Album

4
398 212
Bing Crosby is listed (or ranked) 4 on the list The Greatest Crooners of All Time
Merry Christmas, Bing Crosby's Christmas Classics, White Christmas

5
306 209
Tony Bennett is listed (or ranked) 5 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

6
259 187
Perry Como is listed (or ranked) 6 on the list The Greatest Crooners of All Time
Greatest Christmas Songs, Perry Como Sings Merry Christmas Music, Christmas With Perry Como

7
253 183
Bobby Darin is listed (or ranked) 7 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

8
197 165
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
232 205
Louis Armstrong is listed (or ranked) 9 on the list The Greatest Crooners of All Time
Hot Fives and Hot Sevens, American Freedom, C'est si bon

10
232 174
Andy Williams is listed (or ranked) 10 on the list The Greatest Crooners of All Time
We Need a Little Christmas, The Andy Williams Christmas Album, Moon River

11
197 127
Sammy Davis, Jr. is listed (or ranked) 11 on the list The Greatest Crooners of All Time
Christmas With the Rat Pack, Sammy & Friends, Our Shining Hour

12
148 115
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
278 321
George Michael is listed (or ranked) 13 on the list The Greatest Crooners of All Time
Milla added Faith, Listen Without Prejudice, Volume 1

14
147 133
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
227 185
Michael Bublé is listed (or ranked) 15 on the list The Greatest Crooners of All Time
Call Me Irresponsible, White Christmas, First Dance

16
186 152
Ray Charles is listed (or ranked) 16 on the list The Greatest Crooners of All Time
The Birth of Soul, Modern Sounds in Country and Western Music, The Spirit of Christmas

17
111 135
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
105 123
Matt Monro is listed (or ranked) 18 on the list The Greatest Crooners of All Time
Yesterdays, Matt Monro Sings, The Greatest

19
140 133
Tom Jones is listed (or ranked) 19 on the list The Greatest Crooners of All Time
Praise & Blame, Live, She's a Lady

20
75 92
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
77 96
Eddie Fisher is listed (or ranked) 21 on the list The Greatest Crooners of All Time
The Very Best of Eddie Fisher, I'm Yours, Games That Lovers Play

22
121 123
Fred Astaire is listed (or ranked) 22 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

23
176 245
David Bowie is listed (or ranked) 23 on the list The Greatest Crooners of All Time
lisatyd added The Rise and Fall of Ziggy Stardust and the Spiders From Mars, Hunky Dory, Diamond Dogs

24
63 61
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
102 125
Paul Anka is listed (or ranked) 25 on the list The Greatest Crooners of All Time
Rock Swings, Three Great Guys, 32 Greatest Hits

26
94 114
Barry Manilow is listed (or ranked) 26 on the list The Greatest Crooners of All Time

27
71 113
Luther Vandross is listed (or ranked) 27 on the list The Greatest Crooners of All Time
Todd Howard added This Is Christmas, Every Year, Every Christmas

28
81 96
Frankie Avalon is listed (or ranked) 28 on the list The Greatest Crooners of All Time
Venus & Other Hits, The Teen Idols: The Very Best Of, Best of Frankie Avalon [MCA]

29
75 90
Frankie Laine is listed (or ranked) 29 on the list The Greatest Crooners of All Time
This Is Country, 40 Great Performances, 50 Legendary Recordings

30
88 151
Rod Stewart is listed (or ranked) 30 on the list The Greatest Crooners of All Time
Michele Masi added Every Picture Tells a Story, Gasoline Alley, Downtown Train – Selections from the Storyteller Anthology

31
21 13
Steve Lawrence is listed (or ranked) 31 on the list The Greatest Crooners of All Time
ThePapasmurf1946 added Steve Lawrence Sings Sinatra, Go Away Little Girl / If You Love Her Tell Her So, The Steve Lawrence Sound

32
74 97
Al Martino is listed (or ranked) 32 on the list The Greatest Crooners of All Time
Spanish Eyes, The Very Best of Al Martino (disc 2), Evergreen Selection

33
71 103
Pat Boone is listed (or ranked) 33 on the list The Greatest Crooners of All Time
In a Metal Mood: No More Mr. Nice Guy, Love Letters in the Sand, The Best Of Pat Boone

34
59 122
Scott Walker is listed (or ranked) 34 on the list The Greatest Crooners of All Time
lili added Tilt, The Drift, Scott 3

35
56 87
Billy Eckstine is listed (or ranked) 35 on the list The Greatest Crooners of All Time
Stormy / Feel the Warm, Now Singing in 12 Great Movies, Billy Eckstine Sings With Benny Carter

36
9 8
Johnny Mercer is listed (or ranked) 36 on the list The Greatest Crooners of All Time
Lauren Spainhoward added Personality, My Huckleberry Friend

37
3 1
Charles Aznavour is listed (or ranked) 37 on the list The Greatest Crooners of All Time
Abgar Danielian added Christmas in Vienna III, 40 Chansons d'Or (disc 1), Paris — Palais des Congrès: Intégrale du spectacle

38
6 6
Louis Prima is listed (or ranked) 38 on the list The Greatest Crooners of All Time
SteveLevine added Louis Prima: Capitol Collector's Series, The Wildest!, Buona Sera

39
70 116
John Legend is listed (or ranked) 39 on the list The Greatest Crooners of All Time
Get Lifted, Once Again, Evolver

40
2 0
Barry Manilow is listed (or ranked) 40 on the list The Greatest Crooners of All Time
A Christmas Gift of Love, In the Swing of Christmas, Because It's Christmas

41
54 92
Chris Isaak is listed (or ranked) 41 on the list The Greatest Crooners of All Time
Heart Shaped World, Christmas, Wicked Game

42
29 84
Gene Austin is listed (or ranked) 42 on the list The Greatest Crooners of All Time
Ya Gotta How to Love / Bye Bye Blackbird, Someday Sweetheart / Forgive Me, Five Foot Two Eyes of Blue / Sleepy Time Gal

43
8 14
John Raitt is listed (or ranked) 43 on the list The Greatest Crooners of All Time
ThePapasmurf1946 added Carousel (1945 original Broadway cast), Mediterranean Magic, Broadway Legend

44
28 85
Al Bowlly is listed (or ranked) 44 on the list The Greatest Crooners of All Time
Say, Don't You Remember...?, Essential Collection

45
50 93
Jimmy Durante is listed (or ranked) 45 on the list The Greatest Crooners of All Time
Jimmy Durante's Way of Life, Hello, Young Lovers / One of Those Songs

46
1 7
John Gary is listed (or ranked) 46 on the list The Greatest Crooners of All Time
John Gary Catch a Rising Star / Encore, So Tenderly / A Little Bit of Heaven, The Very Best of John Gary

47
8 17
Leon Redbone is listed (or ranked) 47 on the list The Greatest Crooners of All Time
ThePapasmurf1946 added Christmas Island, Double Time, On the Track

48
9 19
José Feliciano is listed (or ranked) 48 on the list The Greatest Crooners of All Time
ThePapasmurf1946 added Feliz Navidad, And the Sun Will Shine.... Hits, Rarities

49
45 87
Rudy Vallée is listed (or ranked) 49 on the list The Greatest Crooners of All Time
As Time Goes By, The Voice That Had Them Fainting, Collection

50
27 91
Michael Feinstein is listed (or ranked) 50 on the list The Greatest Crooners of All Time
The Power of Two, Hopeless Romantics, Pure Gershwin