The Greatest Jazz Singers of All Time: 20 Voices from Ella to Esperanza

These are the 20 greatest jazz singers of all time in our selection: women and men from the 1920s to today, arranged by era and chosen for their records and their influence on the singers who followed. Louis Armstrong, Billie Holiday, Ella Fitzgerald and Sarah Vaughan are the four we consider essential, and the list ends with five singers still recording, among them Samara Joy and Esperanza Spalding. Separate guides, linked below, go deeper on female, male, modern, Black and 1920s jazz singers.

What Makes a Great Jazz Singer

A jazz singer treats a song the way a jazz instrumentalist treats a tune: as material to reshape. Three things set the best apart. The first is time, placing words ahead of or behind the beat so that the phrasing carries the feeling. The second is improvisation, from small changes in the melody to scat, the wordless singing Louis Armstrong made famous in 1926. The third is sound: a tone you recognize within a few notes.

Some singers go further with vocalese, lyrics written to recorded instrumental solos, a style Eddie Jefferson pioneered and Jon Hendricks and Kurt Elling extended. The 20 below are numbered by era, not ranked against each other, and each entry names a record to start with.

The First Great Jazz Singers: 1920s to 1940s

1. Louis Armstrong (1901-1971)

Armstrong sang the way he played trumpet, bending melodies and placing words off the beat. He was not the first to scat on record, but his Hot Five side “Heebie Jeebies” (Okeh, 1926) made scat famous, and Billie Holiday named his “West End Blues” (1928) as her first experience of scat singing. Start with: “West End Blues” and Louis Armstrong Plays W.C. Handy (Columbia, 1954).

2. Billie Holiday (1915-1959)

Holiday’s phrasing, modeled on jazz instrumentalists, changed how singers handle melody and tempo. Her 1930s sides with pianist Teddy Wilson, often with Lester Young, who named her “Lady Day,” are the core of her catalog, and “Strange Fruit” (Commodore, 1939) became her biggest-selling record. Start with: “Strange Fruit” and Lady in Satin (Columbia, 1958).

3. Ella Fitzgerald (1917-1996)

Fitzgerald won an Apollo amateur night at 17 and found fame with Chick Webb’s orchestra on “A-Tisket, A-Tasket” (1938). For Verve she recorded eight Song Book sets (1956 to 1964), and she won 13 Grammys, becoming the first African American woman to win one in 1959. Start with: Ella Fitzgerald Sings the Cole Porter Song Book (Verve, 1956) and Ella in Berlin (Verve, 1960).

4. Nat King Cole (1919-1965)

Cole was a first-rate jazz pianist before he was a star singer, and his King Cole Trio became a model for small jazz groups. From 1950 he worked mainly as a singer, and his diction and warm, even tone made No. 1 hits of “Nature Boy” (1948) and “Mona Lisa” (1950). Start with: After Midnight (Capitol, 1957).

Postwar Voices: 1940s to 1960s

5. Sarah Vaughan (1924-1990)

Vaughan toured in 1943 with Earl Hines’s band, alongside Dizzy Gillespie and Charlie Parker, and sang bebop’s harmonies with a wide range and an almost perfect ear. In 1957 New York Times critic John S. Wilson credited her with “what may well be the finest voice ever applied to jazz.” Start with: Sarah Vaughan (EmArcy, 1955), her only album with Clifford Brown.

6. Frank Sinatra (1915-1998)

Sinatra modeled his long, unbroken phrases on Tommy Dorsey’s trombone, and at Capitol in the 1950s he and arranger Nelson Riddle built albums around a single mood. He did not improvise the way Fitzgerald did, so critics still argue about whether Sinatra was a jazz singer, but Sinatra at the Sands (1966), with Count Basie’s orchestra, swings hard. Start with: In the Wee Small Hours (Capitol, 1955).

7. 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 includes “My Funny Valentine,” the song most associated with him, and entered the Grammy Hall of Fame in 2001. Start with: Chet Baker Sings (Pacific Jazz, 1954).

8. Mel Tormé (1925-1999)

Tormé, a singer, drummer, arranger and co-writer of “The Christmas Song,” disliked his nickname, “the Velvet Fog.” His best jazz work came with arranger Marty Paich on Bethlehem in the 1950s and with pianist George Shearing on Concord, where he won Grammys in 1983 and 1984. Start with: Mel Tormé with the Marty Paich Dek-Tette (Bethlehem, 1956).

9. Johnny Hartman (1923-1983)

Hartman sang with Earl Hines and Dizzy Gillespie in the late 1940s, but one day in 1963 made his name: John Coltrane and Johnny Hartman is the only album Coltrane made as a leader with a singer, and Hartman’s dark, unhurried baritone carries “Lush Life” and “My One and Only Love.” Start with: John Coltrane and Johnny Hartman (Impulse!, 1963).

10. Carmen McRae (1920-1994)

McRae worked as a pianist, including in Benny Carter’s big band, before DownBeat named her best new female vocalist of 1954. She is remembered for behind-the-beat phrasing and an ironic reading of lyrics, and she considered Billie Holiday her main influence. Start with: Carmen McRae Sings Lover Man and Other Billie Holiday Classics (Columbia, 1962).

11. Nina Simone (1933-2003)

Simone trained as a classical pianist and was turned down by the Curtis Institute of Music, a rejection she attributed to racism. Her singing drew on jazz, blues, gospel and folk, and her first single, “I Loves You, Porgy” (1959), reached the Billboard top 20. Start with: Nina Simone in Concert (Philips, 1964), which introduced “Mississippi Goddam.”

12. Tony Bennett (1926-2023)

Bennett began as a Columbia pop hitmaker and moved steadily toward jazz, recording with Art Blakey in 1957 and with the Count Basie Orchestra in 1959. He won 19 competitive Grammys and became an NEA Jazz Master in 2006. Start with: The Tony Bennett/Bill Evans Album (Fantasy, 1975).

Carrying the Tradition: 1970s to 1990s

13. Betty Carter (1929-1998)

Carter sang with Lionel Hampton from 1948 to 1951, where Hampton’s wife named her “Betty Bebop,” and she became known for improvisation and scat that reshaped melodies freely. Refusing to sing pop, she founded her own label, Bet-Car, in 1969, and pianists Mulgrew Miller and Benny Green came through her groups. Start with: The Audience with Betty Carter (Bet-Car, 1980).

14. Cassandra Wilson (1955-2026)

Wilson came up in Steve Coleman’s M-Base collective. Her Blue Note debut, Blue Light ’til Dawn, set songs by Robert Johnson and Joni Mitchell alongside jazz and reached listeners far beyond jazz. She won two Grammys, became an NEA Jazz Master in 2022 and died in September 2026, at 70, as WBGO reported. Start with: Blue Light ’til Dawn (Blue Note, 1993).

15. Dianne Reeves (born 1956)

Reeves grew up in Denver, was invited by trumpeter Clark Terry to sing with him while still in high school, and signed with Blue Note in 1987. Her five Grammys for Best Jazz Vocal Album are the most of any singer in the category; one is for the soundtrack of Good Night, and Good Luck, in which she appears on screen. Start with: The Calling: Celebrating Sarah Vaughan (Blue Note, 2001).

Jazz Singers Today

16. Kurt Elling (born 1967)

Elling left divinity school one credit short of a degree to sing in Chicago clubs. He writes his own vocalese and has won the Grammy for Best Jazz Vocal Album twice: in 2010 for Dedicated to You, a tribute to the Coltrane and Hartman album, and in 2021. Start with: “Nature Boy” from The Messenger (Blue Note, 1997).

17. Gregory Porter (born 1971)

Porter turned to music after a shoulder injury ended his college football career, and he was singing weekly in Harlem when his debut, Water (2010), earned a Grammy nomination. His gospel-rooted baritone has since won Best Jazz Vocal Album twice, in 2014 and 2017. Start with: Liquid Spirit (Blue Note, 2013).

18. Cécile McLorin Salvant (born 1989)

Salvant, born in Miami to a Haitian father and a French mother, studied classical and baroque voice in France and won the Thelonious Monk International Jazz Competition in 2010. She sings in English and French, from 19th-century songs to her own, has won Best Jazz Vocal Album three times and received a MacArthur Fellowship in 2020. Start with: Dreams and Daggers (Mack Avenue, 2017).

19. Samara Joy (born 1999)

Joy grew up in a Bronx gospel family and discovered Sarah Vaughan and Ella Fitzgerald as a student at SUNY Purchase. In 2023 she won the Grammys for Best New Artist and Best Jazz Vocal Album, and she now has six Grammys, including the vocal album award again in 2025 and 2026. Start with: Linger Awhile (Verve, 2022).

20. Esperanza Spalding (born 1984)

Spalding is a bassist as well as a singer, and her music draws on jazz, Brazilian song and funk. Chamber Music Society (2010) led to the 2011 Grammy for Best New Artist, and she has won Best Jazz Vocal Album three times, for Radio Music Society, 12 Little Spells and Songwrights Apothecary Lab. Start with: Chamber Music Society.

More Jazz Singers by Group

Twenty names leave out many great singers. These guides go further:

• The greatest female jazz singers: our ranking of the women who defined jazz singing, from the swing era to today.
• The 20 greatest male jazz singers: Armstrong, Cole and Sinatra on top, plus Billy Eckstine, Jon Hendricks, Joe Williams and Bobby McFerrin.
• Modern jazz singers: 15 singers recording now, including Jazzmeia Horn, Gretchen Parlato, Veronica Swift, José James and Michael Mayo.
• Black jazz singers: 27 African American vocalists by era, from Ma Rainey and Bessie Smith to Samara Joy.
• 1920s jazz singers: the voices of the Jazz Age, when Mamie Smith’s “Crazy Blues” (1920) opened the record business to Black blues singers.

Frequently Asked Questions

Who is the greatest jazz singer of all time?

There is no objective answer, but the strongest cases are Ella Fitzgerald, for her range, her swing and 13 Grammy Awards; Billie Holiday, whose phrasing changed how jazz is sung; and Louis Armstrong, who made scat singing famous in 1926. For sheer voice, our pick is Sarah Vaughan.

Who are the best jazz singers today?

Samara Joy, Cécile McLorin Salvant and Esperanza Spalding have each won the Grammy for Best Jazz Vocal Album three times, and Kurt Elling and Gregory Porter have won it twice each. Dianne Reeves holds the record in the category with five wins.

What is the difference between a jazz singer and a pop singer?

Mostly improvisation and time. A jazz singer changes the melody, rhythm and phrasing from one performance to the next, may scat and responds to the band as it plays; a pop singer usually stays close to the written melody and a fixed arrangement. Tony Bennett and Frank Sinatra worked on both sides of that line.