His music career began in the late 1920s, when, under his real name, he played stride piano in Dixieland jazz bands in Harlem.

[5] He punctuated his piano stylings with a running line of jive patter, which can be traced directly to recordings of the late-1930s jazz personality Tempo King (1915–1939), who was described by columnist Walter Winchell as "the white Fats Waller".

During one audition for a nightclub engagement, where he played piano for a girl singer, he gave his true name of Harry Raab.

He took the boogie woogie beat of his predecessors, but he made it frantic, similar to the rock and roll music of the 1950s.

Other songs that he recorded were "Handsome Harry, the Hipster", "I Stay Brown All Year 'Round", 4-F Ferdinand the Frantic Freak", "Get Your Juices at the Deuces" and "Stop That Dancin' Up There".

He preceded white rock-and-rollers by a decade: the Soundies he recorded are similar to Jerry Lee Lewis's raucous piano numbers of the 1950s.

[9] Like Mezz Mezzrow, Gibson consciously abandoned his ethnicity to adopt black music and culture.

He grew up near Harlem in New York City, and his constant use of black jive talk was not an affectation; it was something he picked up from his fellow musicians.

"After I did the Carnegie Hall concert, I got a write-up in Downbeat and he said the best thing in the whole program was Harry Gibson, the guy that went up and played Bix Beiderbecke solos.

'"[13] Musicraft signed Gibson on the spot, and he recruited drummer Big Sid Catlett and bassist John Simmons for a recording session the next morning, resulting in the hit album Boogie Woogie in Blue.

[16] Although his mainstream movie appearance in Junior Prom was released that year, it could not overcome the notoriety of the "Benzedrine" record.

His comeback resulted in three new albums: Harry the Hipster Digs Christmas, Everybody's Crazy but Me, (its title taken from the lyrics of "Stop That Dancin' Up There") (Progressive, 1986), and Who Put the Benzedrine in Mrs. Murphy's Ovaltine (Delmark, 1989).

The only constants were his tendency to play hard-rocking boogie woogie and his tongue-in-cheek references to drug use.

In 1991, shortly before his death, his family filmed a biographical featurette on his life and music, Boogie in Blue, published as a VHS video that year.