Anita O'Day's unique sound and swinging rhythmic sense put her in the upper echelon of jazz singers, as skillful with ballads as with scatting and liberal interpretations of standard songs. Her career spanned the late swing and bebop eras, inspiring many singers who followed her, such as June Christy, Chris Connor, and Helen Merrill. She began her performing career as a ballroom dance contest winner in the 1930s, which is when she adopted the stage name O'Day. At 19, she began singing professionally in clubs around Chicago.
In 1941 she joined Gene Krupa's big band, recording a memorable duet with Roy Eldridge on "Let Me Off Uptown," one of the first interracial vocal duets on record. She also may have been the first feminist big band singer, refusing to appear in the standard gown and gloves, instead opting for a band jacket and short skirt. She stayed with the Krupa band until 1943. In 1944 she joined Stan Kenton's band. She then re-joined Krupa in 1945, remaining there until 1946, when she began a solo career. In the mid-1950s she made a few notable albums for the Verve label, demonstrating the power of her vocals.
In 1958 her appearance at the Newport Jazz Festival, replete with characteristic big hat, caused a sensation. She provided one of the highlights of the subsequent film of the festival, Jazz on a Summer's Day. From that point on she worked mainly on the club circuit with her own groups.
Always a hit in Japan, she made her first tour there in 1964, returning on several occasions. Frustrated with record label indifference to her artistry, she developed her own record labels. In the 1980s and 1990s, she continued to work the club and jazz festival circuits, including a concert at Carnegie Hall in 1985 to celebrate her 50 years in jazz and notable performances at the Vine Street Bar & Grill in Los Angeles in 1992.
A documentary about the singer's life, Anita O'Day: The Life of a Jazz Singer, won a 2008 Satellite Award from the International Press Academy.
The Complete Recordings, 1949-50, Baldwin Street Music, 1949-50
Swings Cole Porter with Billy May, Verve, 1952-59
Anita Sings the Winners, Verve, 1956-62
Anita Sings the Most, Verve, 1957
Rules of the Road, Pablo, 1993