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The Greatest Jazz Singers Of All Time

Narrowing down a list of the greatest jazz singers of all time would have to include Frank Sinatra, Ella Fitzgerald, Louis Armstrong, Billie Holiday, and Nat “King” Cole. Other important names to consider include Sarah Vaughan, Dinah Washington, and Ray Charles. Here’s a look at some of the top jazz singers over the past century.

Frank Sinatra (1916-1998)

In the 1940s Sinatra was one of the hottest rising young stars in movies and music. His career developed from singing on radio shows with big bands such as those headed by Harry James and Tommy Dorsey. His career blossomed after signing with Capitol Records in 1953 in which his vocals began to emulate the style of horn phrasing. This unique style influenced singers across multiple genres. His recordings ranged from soft to vibrant. One of his most-loved hits was “Theme from New York, New York.”

Ella Fitzgerald (1917-1996)

Known as the “First Lady of Song,” Fitzgerald was a leading vocal force in jazz from the forties through the sixties. Her career initially developed with Chick Webb’s band in the late thirties then working with Norman Granz. She stressed sharp diction in her vocals so that the storytelling was vivid as she fueled recordings with natural upbeat energy. Some of her most popular recordings were “A-Tisket, A-Tasket,” “All of Me” and “It’s Only a Paper Moon.”

Louis Armstrong (1901-1971)

One of the first African-American superstars in the United States, Armstrong helped popularize jazz in the 1920s after performing with King Oliver’s band. Starting in 1929 he began to add skat to his raspy vocal style in his early recordings. The song “All of Me,” which became a standard covered by many artists of the big band era, was a major hit for him in 1932, leading to a consistent string of smash hits through the sixties. His biggest hit was “Hello Dolly” in 1964.

Billie Holiday (1915-1959)

Known as “Lady Day,” Holiday was considered one of the greatest female jazz singers of her time, alongside Ella Fitzgerald. After recording with Benny Goodman in 1933, she went on to have several hits, working with jazz artists such as Teddy Wilson, Count Basie, and Arty Shaw. One of her biggest hits was “Carelessly” in 1937. Her 1939 recording “Strange Fruit” was banned from many radio stations at the time for its controversial lyrics pointing to civil rights reform. It’s now considered a jazz classic in the NARAS Hall of Fame.

Nat “King” Cole (1919-1965)

Cole started out as a jazz pianist then formed the King Cole Trio in 1939 as an instrumental combo. Once Cole began singing on his recordings, his solo career advanced with a long string of hits. He began appearing in movies in 1953 and later hosted a TV series. His soft and smooth singing style made him one of the most popular vocalists of the 20th century. His notable hits included “(I Love You) For Sentimental Reasons,” “Nature Boy” and “Keep Your Kicks On Route 66.” The duet of “Unforgettable” created after his death with daughter Natalie Cole remains one of the most popular jazz recordings ever made.


The world of jazz is very diverse and has been going strong for over a century. When identifying the greatest jazz singers of all time, it’s important to take into account the pioneers who made the music an integral part of American culture. The vocalists listed here are undisputed by jazz authorities as among the greatest.