The 20 Greatest Male Jazz Singers of All Time

These are the 20 male jazz singers who did the most to shape how jazz is sung, ranked on phrasing, improvisation and the recordings other singers learned from rather than on sales. Louis Armstrong is No. 1: his 1926 Hot Five record “Heebie Jeebies” made scat singing a hit, and his phrasing was a formative influence on Bing Crosby and the crooners who followed. The list runs from the 1920s to today, and its second half covers the men who came up from the 1990s on, including Harry Connick Jr., Kurt Elling, Gregory Porter and José James.

The 20 Greatest Male Jazz Singers

1. Louis Armstrong (1901-1971)

Armstrong sang the way he played trumpet, bending the melody and placing words off the beat. He was not the first to scat on record, but “Heebie Jeebies” (Okeh, 1926) made the style famous, and his gravelly tone became one of the most imitated sounds in American music. In 1964 his “Hello, Dolly!” knocked the Beatles off No. 1 on the Billboard Hot 100 and won him a Grammy. See also our ranking of Armstrong's best recordings.

Start with: Louis Armstrong Plays W.C. Handy (Columbia, 1954) and Ella and Louis (Verve, 1956).

2. Nat King Cole (1919-1965)

Cole was a first-rate jazz pianist before he was a star singer, and his King Cole Trio of piano, guitar and bass became a model for small jazz groups. From 1950 he worked mainly as a solo vocalist, and his diction and warm, even tone made No. 1 hits of “Nature Boy” (1948) and “Mona Lisa” (1950). His NBC series The Nat King Cole Show (1956 to 1957) was one of the first network shows hosted by a Black American.

Start with: the small-group session After Midnight (Capitol, 1957).

3. Frank Sinatra (1915-1998)

Sinatra idolized Bing Crosby and modeled his long, unbroken phrases on Tommy Dorsey’s trombone while singing in Dorsey’s band (1940 to 1942). At Capitol in the 1950s, with arranger Nelson Riddle, he made albums built around a single mood. He did not improvise the way Armstrong did, so critics still argue about whether Sinatra counts as a jazz singer, but Sinatra at the Sands (1966), with the Count Basie Orchestra conducted by Quincy Jones, swings as hard as anything here.

Start with: In the Wee Small Hours (Capitol, 1955) and Songs for Swingin’ Lovers! (Capitol, 1956).

4. Billy Eckstine (1914-1993)

Eckstine’s bass-baritone made him a star with Earl Hines’s orchestra (1939 to 1943). In 1944 he formed what is generally considered the first bebop big band, with Charlie Parker, Dizzy Gillespie, Dexter Gordon, Art Blakey, Miles Davis and Sarah Vaughan passing through. His ballads “A Cottage for Sale” and “Prisoner of Love” each sold a million in 1945, and his full-throated style inspired Johnny Hartman, Joe Williams and Lou Rawls.

Start with: his 1940s big-band sides, then the live No Cover, No Minimum (Roulette, 1960).

5. Jon Hendricks (1921-2017)

Hendricks wrote words to instrumental solos and sang them note for note. With Dave Lambert and Annie Ross he multitracked voices in place of the Basie band’s horns on Sing a Song of Basie (1958), and Lambert, Hendricks & Ross won a Grammy for High Flying in 1962. Time magazine called him the “James Joyce of jive,” as its 2017 obituary recalled. He shared the 1986 Grammy for best male jazz vocal with Bobby McFerrin and became an NEA Jazz Master in 1993.

Start with: Sing a Song of Basie (ABC-Paramount, 1958).

6. Mel Tormé (1925-1999)

Tormé was a singer, drummer, arranger and songwriter who co-wrote “The Christmas Song” and hated his nickname, “the Velvet Fog.” His best jazz work came on seven Bethlehem albums with arranger Marty Paich (1955 to 1957) and on six Concord albums with George Shearing, two of which won him Grammys in 1983 and 1984. The Recording Academy lists 2 wins from 14 nominations.

Start with: Mel Tormé with the Marty Paich Dek-Tette (Bethlehem, 1956).

7. Joe Williams (1918-1999)

Williams was the Count Basie Orchestra’s singer from 1954 to 1961, and his 1955 recording of “Every Day I Have the Blues” with Basie entered the Grammy Hall of Fame in 1992. He could shout the blues over a full brass section, then turn to a ballad. Later he worked with Cannonball Adderley and George Shearing, among others, and won a Grammy for Nothin’ but the Blues (Delos, 1983).

Start with: Count Basie Swings, Joe Williams Sings (Clef, 1955).

8. Johnny Hartman (1923-1983)

Hartman sang with Earl Hines and Dizzy Gillespie in the late 1940s, but one day in 1963 made his name. At Rudy Van Gelder’s studio he recorded John Coltrane and Johnny Hartman, the only album Coltrane made as a leader with a singer; Hartman said all but one song were single takes. His dark, unhurried baritone carries “Lush Life” and “My One and Only Love,” and Kurt Elling recorded a full tribute to the album in 2009.

Start with: John Coltrane and Johnny Hartman (Impulse!, 1963).

9. Chet Baker (1929-1988)

Baker became famous in 1952 as the trumpeter in Gerry Mulligan’s quartet, and his soft, close-miked singing matched the restraint of West Coast cool jazz. Chet Baker Sings entered the Grammy Hall of Fame in 2001 and includes “My Funny Valentine,” the song most associated with him. He died in Amsterdam in May 1988 after a fall from his hotel window, four months before the documentary Let’s Get Lost was released.

Start with: Chet Baker Sings (Pacific Jazz, 1954).

10. Tony Bennett (1926-2023)

Bennett began as a Columbia pop hitmaker in the early 1950s and moved steadily toward jazz: The Beat of My Heart (1957) featured Art Blakey and Herbie Mann, and in 1959 he recorded two albums with the Count Basie Orchestra. The Recording Academy lists 19 competitive Grammy wins plus a 2001 Lifetime Achievement Award; his last album, Love for Sale (2021) with Lady Gaga, won Best Traditional Pop Vocal Album. He was named an NEA Jazz Master in 2006.

Start with: The Tony Bennett/Bill Evans Album (Fantasy, 1975).

11. Bing Crosby (1903-1977)

Crosby was one of the first singers to use the microphone for intimacy rather than volume. He came up in the late 1920s as one of Paul Whiteman’s Rhythm Boys, recording alongside Bix Beiderbecke, and Armstrong shaped his phrasing. His jazz side is clearest on those early records and on later work with Armstrong, Ellington and Ella Fitzgerald. In 1963 he became the first recipient of the Grammy Lifetime Achievement Award.

Start with: “From Monday On” (1928), recorded with Whiteman’s orchestra and Beiderbecke.

12. Mark Murphy (1932-2015)

Murphy links Hendricks’s generation to today’s vocalese singers. He recorded Rah with Bill Evans and Clark Terry in the band, moved to London in 1963, and built much of his audience in Europe. From 1972 he made roughly an album a year for Muse, and his own lyric to Oliver Nelson’s “Stolen Moments” became one of his most popular recordings. He won the DownBeat readers’ poll for male vocalist in 1996, 1997, 2000 and 2001.

Start with: Rah (Riverside, 1961) and Stolen Moments (Muse, 1978).

13. Jimmy Scott (1925-2014)

Kallmann syndrome, a rare genetic condition, left Scott with a high contralto voice, which he used with extreme patience, holding phrases far behind the beat. He sang “Everybody’s Somebody’s Fool” with Lionel Hampton’s band, a 1950 R&B hit that did not credit him. Contract disputes then stalled his career for decades. His comeback brought a scene in the final episode of Twin Peaks (1991), a Grammy nomination and an NEA Jazz Master award in 2007.

Start with: All the Way (Sire, 1992), produced by Tommy LiPuma.

14. Bobby McFerrin (born 1950)

McFerrin uses his voice as a whole band, jumping between bass line, melody and percussion. The Voice (1984) was recorded solo with no accompaniment or overdubs, and “Don’t Worry, Be Happy” (1988) became the first a cappella song to top the Billboard Hot 100. He won the Grammy for best male jazz vocal four years running (1986 to 1989), and the Recording Academy lists 10 wins in all.

Start with: The Voice (1984) and the live Spontaneous Inventions (Blue Note, 1986).

15. Kurt Elling (born 1967)

Elling left the University of Chicago Divinity School one credit short of a degree to sing in Chicago clubs, and Blue Note signed him from a demo that became his Grammy-nominated debut. He writes his own vocalese lyrics, in a line that runs from Hendricks through Murphy, and has won the Grammy for Best Jazz Vocal Album twice (2010 and 2021). He is still active, with the Wildflowers duo albums (2024 and 2025) and a 2025 Broadway debut in Hadestown.

Start with: Close Your Eyes (Blue Note, 1995) and Dedicated to You (Concord, 2009).

16. Gregory Porter (born 1971)

Porter came to music late: a shoulder injury ended his college football career, and he was cooking in his brother’s Brooklyn restaurant and singing weekly in Harlem before his debut, Water (Motéma, 2010), earned a Grammy nomination. Liquid Spirit won the Grammy for Best Jazz Vocal Album and reached the UK top 10, and Take Me to the Alley (2016) won the same award in 2017.

Start with: Liquid Spirit (Blue Note, 2013).

17. Andy Bey (1939-2025)

Bey had a four-octave baritone. At 17 he formed Andy and the Bey Sisters, who toured Europe and recorded for RCA Victor and Prestige. He then sang with Horace Silver and Gary Bartz. After years out of view, Ballads, Blues & Bey (1996) brought him back, the Jazz Journalists Association named him Jazz Vocalist of the Year for 2003, and American Song (2004) was nominated for a Grammy.

Start with: Ballads, Blues & Bey (Evidence, 1996) and American Song (Savoy Jazz, 2004).

18. Harry Connick Jr. (born 1967)

Connick trained in New Orleans with Ellis Marsalis and James Booker and was in his early twenties when Rob Reiner asked him to record the standards for When Harry Met Sally… (1989). That soundtrack and the big-band album We Are in Love (1990) won him the Grammy for best male jazz vocal two years running and both went double platinum, bringing Sinatra-era swing to a young audience.

Start with: When Harry Met Sally… (1989) and We Are in Love (1990).

19. Kevin Mahogany (1958-2017)

Mahogany played clarinet and baritone saxophone before he concentrated on singing, and his warm baritone and fluent scat drew comparisons with Eckstine, Williams and Hartman. The Kansas City singer debuted in 1993, played a singer modeled on Big Joe Turner in Robert Altman’s Kansas City (1996), and in 2003 toured as one of the “Four Brothers” with Hendricks, Elling and Murphy.

Start with: Double Rainbow (Enja, 1993).

20. José James (born 1978)

After studying at the New School, James was signed by DJ Gilles Peterson, whose Brownswood label released his 2008 debut, which set jazz singing over hip-hop production. He has moved between those worlds since, from a duo album with pianist Jef Neve (For All We Know, Impulse!, 2010) to Blue Note tributes to Billie Holiday and Bill Withers. His recent albums, 1978 (2024) and its 2025 follow-up, came out on Rainbow Blonde.

Start with: The Dreamer (Brownswood, 2008) and Yesterday I Had the Blues (Blue Note, 2015).

Male Jazz Singers from the 1990s to Today

The 1990s were a revival decade for male jazz vocals: Connick won Grammys in 1990 and 1991, Kevin Mahogany (1993) and Kurt Elling (1995) debuted on jazz labels, and Jimmy Scott and Andy Bey made late comebacks. In the 2000s the biggest sellers came from the pop side of the standards repertoire: Jamie Cullum’s Twentysomething (2003) went platinum in the UK and earned a Grammy nomination, and Michael Bublé’s self-titled 2003 album began a career that has brought him five Grammys.

Five of the twenty are living: McFerrin, Connick, Elling, Porter and James. Elling, Porter and James have all released new music since 2023, so start with them to hear male jazz singing as it sounds now. For younger voices, including Michael Mayo, see our guide to contemporary jazz singers.

Honorable Mentions

• Eddie Jefferson (1918-1979), credited as an innovator of vocalese, wrote the lyric of “Moody’s Mood for Love,” a 1952 hit for King Pleasure.
• Jimmy Rushing (1901-1972), “Mr. Five by Five,” sang the blues with Count Basie’s orchestra from 1935 to 1948.
• Al Jarreau (1940-2017), the “Acrobat of Scat,” won Grammys in both jazz (Look to the Rainbow) and pop (Breakin’ Away).
• Freddy Cole (1931-2020), Nat King Cole’s younger brother, recorded for almost 70 years and earned several Grammy nominations.

For the other half of jazz vocal history, see our ranking of the greatest female jazz singers, or our list of the greatest jazz singers of all time for men and women together.

Frequently Asked Questions

Who is the greatest male jazz singer of all time?

On this list it is Louis Armstrong, because his scat singing and his habit of phrasing like a horn player set the template for jazz singing from the 1920s on. Nat King Cole and Frank Sinatra are the strongest alternatives: Cole for his jazz piano background and diction, Sinatra for his phrasing and his records with the Count Basie Orchestra.

Who are the best male jazz singers today?

Kurt Elling, Gregory Porter and José James are the most prominent male jazz singers still releasing new music. Elling and Porter have each won the Grammy for Best Jazz Vocal Album twice, Elling in 2010 and 2021 and Porter in 2014 and 2017. Harry Connick Jr. and Bobby McFerrin, both on this list, are also living.

Who were the best male swing singers?

Most of them came out of the big bands. Bing Crosby sang with Paul Whiteman in the late 1920s, Frank Sinatra with Tommy Dorsey from 1940 to 1942, Billy Eckstine with Earl Hines from 1939 to 1943, and Jimmy Rushing with Count Basie from 1935 to 1948. Joe Williams sang with Basie from 1954 to 1961, and Harry Connick Jr. revived big-band swing singing around 1990.