Refusing to pander to any female stereotype, O'Day presented herself as a "hip" jazz musician, wearing a band jacket and skirt as opposed to an evening gown.

[1] She started out as a chorus girl in such Uptown venues as the Celebrity Club and the Vanity Fair, and then found work as a singer and waitress at the Ball of Fire, the Vialago, and the Planet Mars.

Her first big break came in 1938 when DownBeat editor Carl Cons hired her to work at his new club at 222 North State Street, the Off-Beat, which became a popular hangout for musicians.

In 1942, she appeared with the Krupa band in two "soundies" (short musical films originally made for jukeboxes), singing "Thanks for the Boogie Ride" and "Let Me Off Uptown".

When Krupa's band broke up,[1] after he was arrested in 1943 for marijuana possession, O'Day joined Woody Herman for a month-long gig at the Hollywood Palladium, followed by two weeks at the Orpheum.

[1] During her 11 months with Kenton, O'Day recorded 21 sides, both transcription and commercial, and appeared in a Universal Pictures short Artistry in Rhythm (1944).

While living with husband Carl Hoff in Los Angeles in March 1947, two undercover policemen came to their home, during a party at which Dizzy Gillespie was playing from the branches of a tree in their front yard.

Her career was back on the upswing in September 1948 when she sang with Count Basie at the Royal Roost in New York City, resulting in five airchecks.

The case was dismissed by a jury for lack of evidence, but while awaiting her trial, O'Day was introduced to sniffing heroin by Harry the Hipster.

O'Day wrote in her 1981 autobiography that when Goodman's attempts to upstage her failed to diminish the audience's enthusiasm, he cut all but two of her numbers from the show.

O'Day went back to touring as a solo artist and appeared on such TV specials as the Timex All-Star Jazz Show and The Swingin' Years hosted by Ronald Reagan.

[1] In November 1980, she was a headliner along with Clark Terry, Lionel Hampton and Ramsey Lewis, during the opening two-week ceremony performances celebrating the short-lived resurgence of the Blue Note Lounge at the Marriott O'Hare Hotel near Chicago.

[1] Following a life-threatening fall down a staircase at the end of 1996, she made a comeback in 1999, resuming her career with the help of long-time manager Alan Eichler.

The feature-length documentary Anita O'Day: The Life of a Jazz Singer, directed by Robbie Cavolina and Ian McCrudden, premiered at the Tribeca Film Festival on April 30, 2007.

[11][13] O'Day cited Martha Raye as the primary influence on her vocal style, also expressing admiration for Mildred Bailey, Ella Fitzgerald, and Billie Holiday.