Beginning her professional career in the late–1950s, her background includes opera training in childhood, performances as a soul balladeer in the 1960s, European tours, and appearances at the Chicago Blues Festival.

Bunky Sheppard discovered Maxwell in early 1965 and produced her first singles for Constellation Records, starting with "One Thin Dime", which received airplay in Chicago.

Star promoted the record with an appearance of deejay Herb Kent at the Crane High School, with Maxwell getting up on the table to sing the song while demonstrating how to do the dance.

[1] Maxwell reached a crossroads in her career when she made the mistake in 1967 of singing the pop song "Misty" while performing at a Chicago R&B nightclub called Peyton Place on the same bill as Hi-Fi White, a blues vocalist and transvestite comedian known for lewd jokes.

[2] When she ran crying to the dressing room after the audience threw oranges and beer bottles at her, White told her, "Honey, you ain't got no soul."

[11] She hosted an all-female performance at the 2011 Chicago Blues Festival, featuring Liz Mandeville, Demetria Taylor, Peaches Staten, and Ramblin' Rose.

American Blues News reported that her early influences included Shirley Temple, Mae West, Marian Anderson, Josephine Baker, and Dinah Shore.

[17][24] In 1978, South African reviewer Roy Christie credited the success of the Jimmy Smith show to "the electrifying performance of Holly Maxwell."

"[25] Reviewer Aaron Cohen more recently described Maxwell's rendition of Billie Holiday's "God Bless the Child" as conveying "outright defiance.

"[23] Blues critic David Whiteis stated in 2009 that Maxwell's performance style evolved from a "sweet voiced 'girl singer' who melted hearts back in the day" to "a growling, provocatively clad sex kitten.

Maxwell wrote that Turner was "a kindly man of depth and generosity" despite his dark side that included serious drug addiction and a toxic, mutually abusive relationship with his wife, Tina.

Whiteis reports that "Maxwell reminds us that Ike Turner’s life and legacy exemplify what Gordon portrayed in It Came from Memphis – 'the grit that produces the pearls'.