Top 20 Crooners of All Time

Crooners: Top 20

According to Wikipedia, “crooners are singers who sing in a soft, intimate style made possible by the introduction of microphones and amplification.” This technological breakthrough made it possible to pick up quieter sounds and a greater frequency range. Prior to such breakthroughs, singers had to be able to project through a very loud vocal style. Crooners often performed in front of big bands. The style grew to its height in popularity in the 1940s through the late ‘60s. It has, however, continued through modern day artists such as Michael Bublé and Harry Connick, Jr. who sing vocal jazz in a style which has come to be labeled as “traditional pop.” This list was created by aggregating 10 lists focused on the best crooners of all time. See other lists of Acts/Music Makers by Categories. Frank Sinatra 1. Frank Sinatra 2. Bing Crosby 3. Nat “King” Cole 4. Tony Bennett 5. Dean Martin 6. Perry Como 7. Johnny Mathis 8. Bobby Darin 9. Sammy Davis, Jr. 10. Mel Tormé 11. Michael Bublé 12. Harry Connick, Jr. 13. Matt Monro 14. Andy Williams 15. Charles Aznavour 16. Louis Armstrong 17. Barry Manilow 18. Tom Jones 19. Eddie Fisher 20. Vic Damone Resources/Related Links: Wikipedia: List of Crooners Dave’s Music Database: Top 25 Traditional Pop/Vocal Jazz Albums Dave’s Music Database: Lists of Acts/Music Makers by Categories First posted 6/29/2026.

 

Dave's Music Database Hall of Fame: Music Maker Inductees (June 2020)

Top 20 Pre-Rock-Era Acts Originally posted 6/22/2020. January 22, 2019 marked the 10-year anniversary of the DMDB blog! To honor that, Dave’s Music Database announced its own Hall of Fame. This sixth batch of music maker inductees celebrates the top Pre-Rock-Era Acts, as determined by rankings in Joel Whitburn’s Pop Memories 1890-1954 (see the list here). These are the top 20 from that list, minus previous inductees, which included Henry Burr, Arthur Collins, Bing Crosby, Tommy Dorsey, Byron Harlan, Guy Lombardo, Billy Murray, Frank Sinatra, and Paul Whiteman. See the full list of music maker inductees here.

The Andrews Sisters (active 1938-1951) Inducted June 2020 as “Top 20 Pre-Rock-Era Act.”

The most popular female vocal group of the pre-rock era. The trio of Patty, Maxene, and LaVerne appeared in many '40s movies and their unmistakable sound helped define the wartime. Had six #1 songs, including “Bei Mir Bist Du Schöen (Means That You’re Grand),” “Ferryboat Serenade,” “Shoo-Shoo Baby,” “Rum and Coca Cola,” “I Can Dream, Can’t I?,” and “I Wanna Be Loved.” However, they are probably best remembered for “Boogie Woogie Bugle Boy.” Read more.

Perry Como (1912-2001) Inducted June 2020 as “Top 20 Pre-Rock-Era Act.”

Italian-American traditional pop crooner born Pierino Ronald Como in Canonsburg, PA. Left his hometown barber shop to sing with Freddie Carlone’s local band in 1933; about four years later Ted Weems hired him as a featured vocalist. When the Weems band broke up in 1942, he secured a local CBS radio show. Once he started recording the following year there was no stopping him. Como’s relaxed style and romantic vocals made his TV series a popular favorite from the early ‘50s to 1963. His version of “Some Enchanted Evening” is featured in the DMDB book The Top 100 Songs of the Pre-Rock Era, 1890-1953. Read more.

Jimmy Dorsey (1904-1957) Inducted June 2020 as “Top 20 Pre-Rock-Era Act.”

Bandleader born in Shenandoah, PA. Used his vast skills as alto-saxophonist and clarinetist with a multitude of bands during the late ‘20s and early ‘30s. He and his brother Tommy Dorsey played with others and each other as the Dorsey Brothers before Jimmy struck out on his own in 1935. “Amapola (Pretty Little Poppy),” “Tangerine,” and “Besame Mucho” are in the DMDB’s top 1% of songs. Read more.

Benny Goodman (1909-1986) Inducted June 2020 as “Top 20 Pre-Rock-Era Act.”

Jazz clarinetist and bandleader born in Chicago, Illinois. Known as "The King of Swing" for ushering in more dance-oriented jazz. Was in a band by age 14. Worked with multiple noted artists before forming his own band in 1934. He launched the careers of many other jazz musicians including guitarist Charlie Christian and drummer Gene Krupa and was one of the first to lead integrated jazz groups. His 1/16/1938 Carnegie Hall concert in New York is, as All Music Guide’s Bruce Eder called it, “the single most important jazz or popular music concert in history.” Read more.

Al Jolson (1886-1950) Inducted June 2020 as “Top 20 Pre-Rock-Era Act.”

Jazz singer born Asa Yoelson in St. Petersburg, Russia. One of the greatest popular entertainers in American history, becoming a star with minstrel shows, vaudeville, Broadway, and movies, specifically in 1927’s The Jazz Singer, which ushered in the age of sound motion pictures. “You Made Me Love You, I Didn't Want to Do It,” “Rock-a-Bye Your Baby with a Dixie Melody,” “Swanee,” “April Showers,” and “Sonny Boy” are featured in the DMDB book The Top 100 Songs of the Pre-Rock Era, 1890-1953. Read more.

Sammy Kaye (1910-1987) Inducted June 2020 as “Top 20 Pre-Rock-Era Act.”

Jazz/big band leader born Samuel Zamocay, Jr. in Lakewood, Ohio. Durable leader of popular “sweet” dance band with the slogan “Swing and Sway with Sammy Kaye.” Also clarinet and alto saxman, as well as a composer (“Remember Pearl Harbor”). His song “Daddy” is in the DMDB’s top 1% of songs. Read more.

Ted Lewis (1890-1971) Inducted June 2020 as “Top 20 Pre-Rock-Era Act.”

Bandleader, clarinetist, and singer born Theodore Friedman in Circleville, Ohio. Sometime songwriter (his theme “When My Baby Smiles at Me”) whose showmanship was honed during early years in vaudeville. His famous slogan was “Is everybody happy?” “On the Sunny Side of the Street” is featured in the DMDB book The Top 100 Songs of the Pre-Rock Era, 1890-1953. Read more.

Harry Macdonough (1871-1931) Inducted June 2020 as “Top 20 Pre-Rock-Era Act.”

Tenor singer born John Scantlebury MacDonald in Ontario, Canada. Second only to Henry Burr among the great ballad singers of recordings’ pioneer pre-1920 era. Worked with the Edison Male Quartette, Haydn Quartet, Orpheus Quartet, Lyric Quartet, and Victor Light Opera Co. Was a top record company executive after World War I. “Shine on, Harvest Moon” and “Down by the Old Mill Stream” are featured in the DMDB book The Top 100 Songs of the Pre-Rock Era, 1890-1953. Read more.

Glenn Miller (1904-1944) Inducted June 2020 as “Top 20 Pre-Rock-Era Act.”

Jazz/big band leader born Alton Glenn Miller on 3/1/1904 in Clarinda, IA. Led of the most universally beloved of all big bands. Played trombone and did arrangements for others before starting his own band in 1937. He enlisted in the Army Air Force in September 1942, and formed the war’s most famous service band. Died on 12/15/1944 when his plane was lost over the English Channel. “In the Mood” and “Chattanooga Choo Choo” are featured in the DMDB book The Top 100 Songs of the Pre-Rock Era, 1890-1953. Read more.

Peerless Quartet (active 1907-1928) Inducted June 2020 as “Top 20 Pre-Rock-Era Act.”

All-time great vocal group which began as the Columbia Male Quartet. Members included Henry Burr, Albert Campbell, Steve Porter, Frank Stanley, Arthur Collins, John Meyer, and Frank Croxton. Their song “Let Me Call You Sweetheart” is featured in the DMDB book The Top 100 Songs of the Pre-Rock Era, 1890-1953. Read more.

Charles Adams Prince (1869-1937) Inducted June 2020 as “Top 20 Pre-Rock-Era Act.”

Band leader, pianist and celesta player. Musical director of Columbia Records from the turn of the century to the early 1920s. During that period, his band accompanied virtually every singer recording for Columbia. His orchestra charted 82 times between 1905 and 1923, including the #1 hits “Ballin’ the Jack” (DMDB’s 1914 song of the year), “Hello, Hawaii, How Are You?,” and a version of “The Star-Spangled Banner.” Read more.

Ben Selvin (1898-1980) Inducted June 2020 as “Top 20 Pre-Rock-Era Act.”

Jazz/big band leader and violinist. His 2000+ recordings were more than any other bandleader. He charted more than 100 times, including eight #1 hits. “Dardanella,” “Blue Skies,” and “Happy Days Are Here Again” are featured in the DMDB book The Top 100 Songs of the Pre-Rock Era, 1890-1953. Read more.

Popular Music Hall of Fame: years unknown

This Hall seems to be defunct now. Web searches only turn up the more recent America’s Pop Music Hall of Fame and the pophall.org link is now dead. The Hall had 25 inductees from the pre-rock era. See other Hall of Fames. The Andrews Sisters Tony Bennett Irving Berlin Hoagy Carmichael Rosemary Clooney Nat “King” Cole Perry Como Bing Crosby Dr. Lee DeForest Walt Disney Tommy Dorsey Thomas Edison Judy Garland George Gershwin Benny Goodman Al Jolson Jerome Kern Glenn Miller The Mills Brothers Patti Page Cole Porter David Sarnoff Frank Sinatra Kate Smith Ed Sullivan Resources/Related Links: Dave’s Music Database: “Hall of Fames” Popular Music Hall of Fame First posted 12/19/2012; last updated 7/12/2025.

The Top 100 Music Makers of the Pre-Rock Era (1890-1953)

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After a couple treks WAY down memory lane this last week (Duke Ellington’s 1941 “Take the ‘A’ Train” and Tommy Dorsey and Frank Sinatra’s 1940 “I’ll Never Smile Again”), the timing was right for a glimpse at the biggest music makers of the pre-rock era. Music makers is an all-encompasing term used to embrace individual performers, groups, songwriters, and others involved in the creation of music. This list is dominated by performers, but there are some notable songwriters and composers on the list. Music makers who debuted from 1954 on were disqualified from this list so don’t look for Elvis Presley and his ilk here! Click on names to see their entries in the Dave’s Music Database Music Makers Encyclopedia.

1. Bing Crosby
2. Frank Sinatra
3. Paul Whiteman Orchestra
4. Tommy Dorsey
5. Benny Goodman
6. Billy Murray
7. Guy Lombardo
8. Louis Armstrong
9. Perry Como
10. Nat “King” Cole



Bing Crosby

11. Glenn Miller
12. Duke Ellington
13. Henry Burr
14. Al Jolson
15. Fats Domino
16. Jimmy Dorsey
17. The Andrews Sisters
18. Byron G. Harlan
19. Arthur Collins
20. Peerless Quartet/Columbia Male Quartet



Frank Sinatra

21. Billie Holiday
22. Ella Fitzgerald
23. Sammy Kaye
24. Harry MacDonough
25. Ben Selvin
26. Ted Lewis & His Band
27. Patti Page
28. Fats Waller
29. Frankie Laine
30. Jo Stafford



Paul Whiteman

31. Mills Brothers
32. Freddy Martin
33. Harry James
34. Eddy Arnold
35. Dinah Shore
36. Muddy Waters
37. Robert Johnson
38. Isham Jones
39. Kay Kyser
40. Leo Reisman



Tommy Dorsey

41. Haydn Quartet
42. Vaughn Monroe Orchestra
43. Rudy Vallee
44. Irving Berlin
45. Glen Gray & The Casa Loma Orchestra
46. George Gershwin
47. Eddie Fisher
48. Ada Jones
49. Gene Austin
50. American Quartet



Benny Goodman

51. Eddy Duchin
52. Artie Shaw
53. Hal Kemp
54. Ray Noble
55. Count Basie
56. Charles Adams Prince/Prince’s Orchestra
57. Jan Garber Orchestra
58. Russ Morgan
59. Ink Spots
60. John McCormack



Billy Murray

61. Fred Waring
62. Ruth Etting
63. Igor Stravinsky
64. Woody Herman
65. George Olsen & His Orchestra
66. Marion Harris
67. Richard Rodgers
68. Doris Day
69. Louis Jordan
70. Enrico Caruso



Guy Lombardo

71. Les Paul
72. Thelonious Monk
73. Gene Autry
74. Dick Haymes
75. Woody Guthrie
76. Albert Campbell
77. Nat Shilkret
78. Cab Calloway
79. Jerome Kern
80. Oscar Hammerstein II



Louis Armstrong

81. Teddy Wilson & His Orchestra
82. Bessie Smith
83. Margaret Whiting
84. Ted Weems Orchestra
85. Dizzy Gillespie
86. Peggy Lee
87. Fred Astaire
88. Rosemary Clooney
89. Horace Heidt
90. Len Spencer



Perry Como

91. Charlie Parker
92. Eddy Howard Orchestra
93. Bob Crosby
94. Shep Fields
95. Marty Robbins
96. Jimmie Rodgers
97. Ira Gershwin
98. Ozzie Nelson
99. Roy Acuff
100. Ben Bernie



Nat “King” Cole

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Resources and Related Links:

• Dave’s Music Database Music Makers Encyclopedia
  

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100 years ago: Henry Burr took “I Wonder Who’s Kissing Her Now” to #1

I Wonder Who’s Kissing Her Now Henry Burr

Writer(s): Joseph E. Howard and Harold Orlob (music), Frank R. Adams and Will M. Hough (lyrics) (see lyrics here) First Charted: September 4, 1909 Peak: 18 US, 12 GA, 14 SM (Click for codes to singles charts.) Sales (in millions): 3.0 (sheet music) Airplay/Streaming (in millions): -- radio, -- video, -- streaming

Awards: Click on award for more details.

About the Song: This “evergreen standard” JA is “one of the most popular songs in the history of Tin Pan Alley… Considered cliche today, the number’s flowing music, and heartbreaking lyric made it one of the first conversational and down-to-earth torch songs.” RCG It was, however, also controversial because it described a promiscuous relationship. SM The song was selected by ASCAP as one of only sixteen in its All-Time Hit Parade. TY2 Joe Howard claimed he heard a college student in Chicago utter the title phrase and then turned to Frank Adams to write words. RCG The song appeared in the Broadway musical The Prince of Tonight, performed by Henry Woodruff, SMbut it really took off when Howard sang it in the show Miss Nobody from Starland (1910). There was, however, also a claim that it originated from a different musical, The Goddess of Liberty, performed by Edward Abeles as Lord Jack Wyngate. SM Henry Burr’s chart-topping version was followed by two top ten versions by Billy Murray, #4) and (Manuel Romain, #6) the next year. In 1947, the song was revived in a 1947 biopic of the same name about Howard, resulting in three more charted versions – Perry Como with Ted Weems (#2), Ray Noble (#11), and Dinning Sisters (#12). The song sold three million in sheet music sales. The renewed interest in the song also brought about a court case in which musical arranger Harold Orlob sued Howard. JA The case established that Howard had commissioned Orlob to compose the song and then published it as his own. However, Howard had already received royalties for 38 years and although Orlob was given the lead songwriting credit, he didn’t receive any additional money since he’d already been compensated for his work. TY1 Resources: DJ David Jasen (2002). A Century of American Popular Music: 2000 Best-Loved and Remembered Songs (1899-1999). Routledge: Taylor & Francis, Inc. Page 91 SM Sharon Mawer Charts (1900-1968) RCG RimChiGuy.com The Old Songs (1900-1929) TY1 Don Tyler (1985). Hit Parade 1920-1955. New York, NY: Quill. Page 132. TY2 Don Tyler (2007). Hit Songs, 1900-1955. McFarland & Company, Inc.: Jefferson, North Carolina. Pages 42-3. Related Links: First posted 9/11/2016; last updated 12/15/2022.

100 years ago: “When You Were Sweet Sixteen” hit #1

When You Were Sweet Sixteen George J. Gaskin

Writer(s): James Thornton (see lyrics here) First Charted: November 10, 1900 Peak: 18 US, 2 GA (Click for codes to singles charts.) Sales (in millions): 1.0 (sheet music) Airplay/Streaming (in millions): -- radio, -- video, -- streaming

Awards: Click on award for more details.

About the Song: James Thornton was a songwriter and vaudeville performer born in Dublin, Ireland, in 1861. He started out as a singing waiter before finding success doing comedy in music halls. However, he also composed songs, eventually becoming one of the greatest Tin Pan Alley songwriters. WT He was inspired by his wife, Bonnie, to write “When You Were Sweet Sixteen.” She tried to keep him from spending all his money on alcohol and when he came home drunk on Independence Day, WT she tearfully questioned if he still loved her. He replied that he loved her as much as he did when she was sixteen. She encouraged him to turn it into a song. TY2 He did, and she introduced the song in her act. The ballad became a hit vaudeville song and became a standard for barbershop quartets. WW George J. Gaskin, nicknamed the “silver-voiced Irish tenor,” WG had the most successful recording of the song. He was born in Belfast, Ireland, in 1863 but came to the United States as a teenager. He started recording with the Edison North American Phonograph Company in 1891, specializing in Tin Pan Alley songs and sentimental Irish ballads. WG He landed twenty #1 hits over the next decade. His final chart-topper was “When We Were Sweet Sixteen.” Gaskin wasn’t the first to chart with the song, or even the first to hit #1. In March 1900, Jere Mahoney charted with it, taking it to #1 for five weeks. The following year J.W. Myers and Harry MacDonough both reached #3 with their versions. The song saw a revival in 1947 after it appeared in The Jolson Story. Al Jolson took it to #1 in Australia. Perry Como’s million-selling version reached #2 in the United States, followed by top 20 versions by Dick Jurgens and the Mills Brothers. The song resurfaced again in 1981 when the Fureys went to #14 with it in the UK. The song was also featured in the Shirley Temple film Little Miss Broadway (1938), The Strawberry Blond (1941), and Bing Crosby sang it on the soundtrack for The Great John L. (1945). TY2 Resources: DMDB encyclopedia entry for George J. Gaskin TY2 Don Tyler (2007). Hit Songs, 1900-1955. McFarland & Company, Inc.: Jefferson, North Carolina. Pages 12-3. WG Wikipedia page for George J. Gaskin WT Wikipedia page for James Thornton WW Wikipedia page for “When You Were Sweet Sixteen” First posted 12/2/2022; last updated 12/14/2022.