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.

1
551 275
Frank Sinatra is listed (or ranked) 1 on the list The Greatest Crooners of All Time
Frank Sinatra Christmas With the Rat Pack, In the Wee Small Hours, Christmas Songs by Sinatra

2
500 243
Dean Martin is listed (or ranked) 2 on the list The Greatest Crooners of All Time
Dean Martin Christmas With the Rat Pack, Dino / You're the Best Thing That Ever Happened to Me, A Winter Romance

3
408 214
Nat King Cole is listed (or ranked) 3 on the list The Greatest Crooners of All Time
Nat King Cole Merry Christmas, The Magic of Christmas, The Nat King Cole Christmas Album

4
384 210
Bing Crosby is listed (or ranked) 4 on the list The Greatest Crooners of All Time
Bing Crosby Merry Christmas, Bing Crosby's Christmas Classics, White Christmas

5
300 204
Tony Bennett is listed (or ranked) 5 on the list The Greatest Crooners of All Time
Tony Bennett Snowfall: The Tony Bennett Christmas Album, I Left My Heart in San Francisco, A Swingin' Christmas

6
249 180
Bobby Darin is listed (or ranked) 6 on the list The Greatest Crooners of All Time
Bobby Darin 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

7
250 183
Perry Como is listed (or ranked) 7 on the list The Greatest Crooners of All Time
Perry Como Greatest Christmas Songs, Perry Como Sings Merry Christmas Music, Christmas With Perry Como

8
226 200
Louis Armstrong is listed (or ranked) 8 on the list The Greatest Crooners of All Time
Louis Armstrong Hot Fives and Hot Sevens, American Freedom, C'est si bon

9
188 161
Johnny Mathis is listed (or ranked) 9 on the list The Greatest Crooners of All Time
Johnny Mathis Merry Christmas, Christmas With Johnny Mathis, A Personal Collection: The Christmas Music of Johnny Mathis

10
222 172
Andy Williams is listed (or ranked) 10 on the list The Greatest Crooners of All Time
Andy Williams We Need a Little Christmas, The Andy Williams Christmas Album, Moon River

11
144 112
Mel Tormé is listed (or ranked) 11 on the list The Greatest Crooners of All Time
Mel Tormé Complete Concord Recordings, Christmas Songs, Lulu's Back In Town

12
190 124
Sammy Davis, Jr. is listed (or ranked) 12 on the list The Greatest Crooners of All Time
Sammy Davis, Jr. Christmas With the Rat Pack, Sammy & Friends, Our Shining Hour

13
277 314
George Michael is listed (or ranked) 13 on the list The Greatest Crooners of All Time
Milla added George Michael Faith, Listen Without Prejudice, Volume 1

14
141 127
Harry Connick, Jr. is listed (or ranked) 14 on the list The Greatest Crooners of All Time
Harry Connick, Jr. What a Night! A Christmas Album, When My Heart Finds Christmas, Blue Light

15
219 180
Michael Bublé is listed (or ranked) 15 on the list The Greatest Crooners of All Time
Michael Bublé Call Me Irresponsible, White Christmas, First Dance

16
183 148
Ray Charles is listed (or ranked) 16 on the list The Greatest Crooners of All Time
Ray Charles The Birth of Soul, Modern Sounds in Country and Western Music, The Spirit of Christmas

17
107 131
Engelbert Humperdinck is listed (or ranked) 17 on the list The Greatest Crooners of All Time
Engelbert Humperdinck Love Rollercoaster, The Magic of Christmas, Hello Out There

18
102 117
Matt Monro is listed (or ranked) 18 on the list The Greatest Crooners of All Time
Matt Monro Yesterdays, Matt Monro Sings, The Greatest

19
135 132
Tom Jones is listed (or ranked) 19 on the list The Greatest Crooners of All Time
Tom Jones Praise & Blame, Live, She's a Lady

20
72 93
Eddie Fisher is listed (or ranked) 20 on the list The Greatest Crooners of All Time
Eddie Fisher The Very Best of Eddie Fisher, I'm Yours, Games That Lovers Play

21
70 91
Robert Goulet is listed (or ranked) 21 on the list The Greatest Crooners of All Time
Robert Goulet Camelot (1960 original Broadway cast), 16 Most Requested Songs, Greatest Hits

22
175 239
David Bowie is listed (or ranked) 22 on the list The Greatest Crooners of All Time
lisatyd added David Bowie The Rise and Fall of Ziggy Stardust and the Spiders From Mars, Hunky Dory, Diamond Dogs

23
113 121
Fred Astaire is listed (or ranked) 23 on the list The Greatest Crooners of All Time
Fred Astaire "Nice Work": Fred Astaire Sings Gershwin, They Can't Take That Away From Me / Beginner's Luck, The Complete London Sessions

24
61 58
Jerry Vale is listed (or ranked) 24 on the list The Greatest Crooners of All Time
horseplayer added Jerry Vale Christmas Greetings From Jerry, Jerry Vale 17 Most Requested Songs, Great Italian Hits

25
92 111
Barry Manilow is listed (or ranked) 25 on the list The Greatest Crooners of All Time

26
69 109
Luther Vandross is listed (or ranked) 26 on the list The Greatest Crooners of All Time
Todd Howard added Luther Vandross This Is Christmas, Every Year, Every Christmas

27
99 124
Paul Anka is listed (or ranked) 27 on the list The Greatest Crooners of All Time
Paul Anka Rock Swings, Three Great Guys, 32 Greatest Hits

28
87 145
Rod Stewart is listed (or ranked) 28 on the list The Greatest Crooners of All Time
Michele Masi added Rod Stewart Every Picture Tells a Story, Gasoline Alley, Downtown Train – Selections from the Storyteller Anthology

29
77 95
Frankie Avalon is listed (or ranked) 29 on the list The Greatest Crooners of All Time
Frankie Avalon Venus & Other Hits, The Teen Idols: The Very Best Of, Best of Frankie Avalon [MCA]

30
72 89
Frankie Laine is listed (or ranked) 30 on the list The Greatest Crooners of All Time
Frankie Laine This Is Country, 40 Great Performances, 50 Legendary Recordings

31
72 95
Al Martino is listed (or ranked) 31 on the list The Greatest Crooners of All Time
Al Martino Spanish Eyes, The Very Best of Al Martino (disc 2), Evergreen Selection

32
18 12
Steve Lawrence is listed (or ranked) 32 on the list The Greatest Crooners of All Time
ThePapasmurf1946 added Steve Lawrence Steve Lawrence Sings Sinatra, Go Away Little Girl / If You Love Her Tell Her So, The Steve Lawrence Sound

33
59 118
Scott Walker is listed (or ranked) 33 on the list The Greatest Crooners of All Time
lili added Scott Walker Tilt, The Drift, Scott 3

34
68 101
Pat Boone is listed (or ranked) 34 on the list The Greatest Crooners of All Time
Pat Boone In a Metal Mood: No More Mr. Nice Guy, Love Letters in the Sand, The Best Of Pat Boone

35
56 85
Billy Eckstine is listed (or ranked) 35 on the list The Greatest Crooners of All Time
Billy Eckstine Stormy / Feel the Warm, Now Singing in 12 Great Movies, Billy Eckstine Sings With Benny Carter

36
5 4
Louis Prima is listed (or ranked) 36 on the list The Greatest Crooners of All Time
SteveLevine added Louis Prima Louis Prima: Capitol Collector's Series, The Wildest!, Buona Sera

37
6 6
Johnny Mercer is listed (or ranked) 37 on the list The Greatest Crooners of All Time
Lauren Spainhoward added Johnny Mercer Personality, My Huckleberry Friend

38
67 113
John Legend is listed (or ranked) 38 on the list The Greatest Crooners of All Time
John Legend Get Lifted, Once Again, Evolver

39
1 5
John Gary is listed (or ranked) 39 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

40
28 82
Gene Austin is listed (or ranked) 40 on the list The Greatest Crooners of All Time
Gene Austin Ya Gotta How to Love / Bye Bye Blackbird, Someday Sweetheart / Forgive Me, Five Foot Two Eyes of Blue / Sleepy Time Gal

41
52 90
Chris Isaak is listed (or ranked) 41 on the list The Greatest Crooners of All Time
Chris Isaak Heart Shaped World, Christmas, Wicked Game

42
28 83
Al Bowlly is listed (or ranked) 42 on the list The Greatest Crooners of All Time
Al Bowlly Say, Don't You Remember...?, Essential Collection

43
9 16
José Feliciano is listed (or ranked) 43 on the list The Greatest Crooners of All Time
ThePapasmurf1946 added José Feliciano Feliz Navidad, And the Sun Will Shine.... Hits, Rarities

44
7 13
John Raitt is listed (or ranked) 44 on the list The Greatest Crooners of All Time
ThePapasmurf1946 added John Raitt Carousel (1945 original Broadway cast), Mediterranean Magic, Broadway Legend

45
8 15
Leon Redbone is listed (or ranked) 45 on the list The Greatest Crooners of All Time
ThePapasmurf1946 added Leon Redbone Christmas Island, Double Time, On the Track

46
49 92
Jimmy Durante is listed (or ranked) 46 on the list The Greatest Crooners of All Time
Jimmy Durante Jimmy Durante's Way of Life, Hello, Young Lovers / One of Those Songs

47
44 86
Rudy Vallée is listed (or ranked) 47 on the list The Greatest Crooners of All Time
Rudy Vallée As Time Goes By, The Voice That Had Them Fainting, Collection

48
27 88
Michael Feinstein is listed (or ranked) 48 on the list The Greatest Crooners of All Time
Michael Feinstein The Power of Two, Hopeless Romantics, Pure Gershwin

49
34 82
Johnny Hartman is listed (or ranked) 49 on the list The Greatest Crooners of All Time
Johnny Hartman The Voice That Is!, John Coltrane and Johnny Hartman, Songs From the Heart

50
17 80
Art Gillham is listed (or ranked) 50 on the list The Greatest Crooners of All Time
Art Gillham I'm Sitting on Top of the World / You're More Than a Pal to Me