Born in Chicago,[1] Kirby broke into show business in the 1940s at the Club DeLisa, a South Side establishment that employed a variety-show format and preferred to hire local singers, dancers, and comedians.

Kirby was also a bebop piano player and did song and vocal impressions of jazz greats Louis Armstrong, Nat King Cole, Ella Fitzgerald, and Joe Williams.

The series was in many ways an uneasy compromise between Kirby's natural gifts and what the public would accept of Black actors at the time; a regular feature was a shaggy dog story entitled the "Funky Fable".

HBO did include him in their On Location With comedian series in the late 1970s, filming one of his many appearances at Grossinger's in the NY Catskills, a club he had played regularly since 1961.

[2] Diagnosed with Parkinson's disease in his later years, Kirby made his last public appearance at an all-star benefit in May 1995 given by his friends for his mounting medical bills.