Chicago soul vocalist Holly Maxwell started singing with the Tourjourettes while attending Parker High School; she studied classical music at Chicago Musical College in 1965 and never considered herself a soul singer. A deal with Constellation Records ended her schooling. The release of "Happiness Will Cost You One Thin Dime" b/w "It's Impossible" in June 1965 set her on a lifelong musical career; the recording did nothing regionally or nationally, but sold locally. Two months later, Constellation issued another local hit, the pretty "Only When You're Lonely" b/w "Let Him Go for Himself." She went with Star Records for at least two releases in 1966: the dancer "Philly Barracuda" and "Don't Say You Love Me Until You Do" b/w "Blueberry Hill."
One single resulted from a deal with Curtom Records in 1969, "Suffer" b/w "No One Else." Patti Labelle & the Blue Belles remade "Suffer" on Atlantic Records in 1969; Curtis Mayfield later cut the song on his Sweet Exorcist album; the Impressions originally recorded "No One Else." In addition to her solo gigs in Chicago clubs, Maxwell occasionally sang background for Barbara Acklin. In 1970, she cut a single for Smit-Whit Records: "Never Love Again" b/w "Winter Go Away."
Maxwell moved to California in the '70s and worked with Ike Turner as Tina Turner's fill-in. In California she owned a club and sang jazz, but by 1985 had resettled in Chicago. She never stopped performing, and was a regular at Maxwell's Cafe (no relation) in Paris, France; she has appeared with the Fins, Lee "Shot" Wiliams, Johnny Mars, and guitarist/singer Charles Love. She has also been a nightclub figure in London and other European countries.