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
522 265
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
471 231
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
383 209
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
367 201
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
282 201
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
241 180
Perry Como is listed (or ranked) 6 on the list The Greatest Crooners of All Time
Perry Como Greatest Christmas Songs, Perry Como Sings Merry Christmas Music, Christmas With Perry Como

7
234 175
Bobby Darin is listed (or ranked) 7 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

8
213 192
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
178 154
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
213 169
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
276 303
George Michael is listed (or ranked) 11 on the list The Greatest Crooners of All Time
Milla added George Michael Faith, Listen Without Prejudice, Volume 1

12
136 107
Mel Tormé is listed (or ranked) 12 on the list The Greatest Crooners of All Time
Mel Tormé Complete Concord Recordings, Christmas Songs, Lulu's Back In Town

13
176 120
Sammy Davis, Jr. is listed (or ranked) 13 on the list The Greatest Crooners of All Time
Sammy Davis, Jr. Christmas With the Rat Pack, Sammy & Friends, Our Shining Hour

14
132 124
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

Famous Crooners

15
207 174
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
174 144
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
103 126
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
90 114
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
172 229
David Bowie is listed (or ranked) 19 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

20
124 130
Tom Jones is listed (or ranked) 20 on the list The Greatest Crooners of All Time
Tom Jones Praise & Blame, Live, She's a Lady

21
110 114
Fred Astaire is listed (or ranked) 21 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

The Best Convertibles of All Time

22
67 91
Eddie Fisher is listed (or ranked) 22 on the list The Greatest Crooners of All Time
Eddie Fisher The Very Best of Eddie Fisher, I'm Yours, Games That Lovers Play

23
63 86
Robert Goulet is listed (or ranked) 23 on the list The Greatest Crooners of All Time
Robert Goulet Camelot (1960 original Broadway cast), 16 Most Requested Songs, Greatest Hits

24
56 53
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
87 137
Rod Stewart is listed (or ranked) 25 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

26
75 90
Frankie Avalon is listed (or ranked) 26 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]

27
94 119
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
70 83
Frankie Laine is listed (or ranked) 28 on the list The Greatest Crooners of All Time
Frankie Laine This Is Country, 40 Great Performances, 50 Legendary Recordings

The (Male) Singer You Most Wish You Could Sound Like

29
86 107
Barry Manilow is listed (or ranked) 29 on the list The Greatest Crooners of All Time

30
63 105
Luther Vandross is listed (or ranked) 30 on the list The Greatest Crooners of All Time
Todd Howard added Luther Vandross This Is Christmas, Every Year, Every Christmas

31
68 90
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
66 94
Pat Boone is listed (or ranked) 32 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

33
58 113
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
12 9
Steve Lawrence is listed (or ranked) 34 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

35
67 105
John Legend is listed (or ranked) 35 on the list The Greatest Crooners of All Time
John Legend Get Lifted, Once Again, Evolver

16 Songs That Don't Mean What You Think They Do

36
0 0
John Gary is listed (or ranked) 36 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

37
9 10
José Feliciano is listed (or ranked) 37 on the list The Greatest Crooners of All Time
ThePapasmurf1946 added José Feliciano Feliz Navidad, And the Sun Will Shine.... Hits, Rarities

38
49 79
Billy Eckstine is listed (or ranked) 38 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

39
7 8
John Raitt is listed (or ranked) 39 on the list The Greatest Crooners of All Time
ThePapasmurf1946 added John Raitt Carousel (1945 original Broadway cast), Mediterranean Magic, Broadway Legend

40
28 77
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
8 10
Leon Redbone is listed (or ranked) 41 on the list The Greatest Crooners of All Time
ThePapasmurf1946 added Leon Redbone Christmas Island, Double Time, On the Track

42
2 1
Johnny Mercer is listed (or ranked) 42 on the list The Greatest Crooners of All Time
Lauren Spainhoward added Johnny Mercer Personality, My Huckleberry Friend

43
50 86
Chris Isaak is listed (or ranked) 43 on the list The Greatest Crooners of All Time
Chris Isaak Heart Shaped World, Christmas, Wicked Game

44
27 79
Al Bowlly is listed (or ranked) 44 on the list The Greatest Crooners of All Time
Al Bowlly Say^! Don't You Remember...?, Essential Collection, Ray Noble - Midnight the Stars and You^! in London 1930-34

45
44 82
Rudy Vallée is listed (or ranked) 45 on the list The Greatest Crooners of All Time
Rudy Vallée As Time Goes By, The Voice That Had Them Fainting, Collection

46
27 84
Michael Feinstein is listed (or ranked) 46 on the list The Greatest Crooners of All Time
Michael Feinstein The Power of Two, Hopeless Romantics, Pure Gershwin

47
46 88
Jimmy Durante is listed (or ranked) 47 on the list The Greatest Crooners of All Time
Jimmy Durante Jimmy Durante's Way of Life, Hello^! Young Lovers / One of Those Songs, September Song

48
31 78
Johnny Hartman is listed (or ranked) 48 on the list The Greatest Crooners of All Time
Johnny Hartman The Voice That Is!, John Coltrane and Johnny Hartman, Songs From the Heart

49
17 76
Art Gillham is listed (or ranked) 49 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

50
8 40
Jamie Cullum is listed (or ranked) 50 on the list The Greatest Crooners of All Time
TobiasBrammerKristensen added Jamie Cullum Catching Tales, Twentysomething, Momentum