The Washington Post found the film disappointing: "What we have here is a brilliant concept, but unfortunately, Harris just isn't a filmmaker — not even in the most rudimentary sense.

"[4] Similarly, the Hartford Courant wrote "Chameleon Street feels like a series of improvised skits, some imaginative and funny, some hackneyed...[Harris] writes with élan and wit, but his sense of structure is minimal, so Chameleon Street feels jumpy and disjointed.

"[6] Jonathan Rosenbaum of The Chicago Reader praised it as a "highly original existential dark comedy," writing that "it took two years for this provocative independent feature to reach Chicago, yet it’s as intellectually ambitious as any new American picture I’ve seen this year...Harris explores his subject in a number of ways: as an essay of sorts on the mysteries and paradoxes of acting, as the source of some very funny comedy, as an exploration of the invisibility of blacks in America that often suggests Ralph Ellison’s Invisible Man, and as a disturbing yet compelling rogue’s progress that often calls to mind an 18th-century picaresque novel.

[8] In the years since its original release, the film's reputation has grown, with Richard Brody of The New Yorker in 2021 calling it an "overlooked masterpiece" while lamenting Harris's subsequent struggles in Hollywood, observing that "the very exclusions [Harris] dramatized in this great film were inflicted on him in real life.

[12][13] In 2008, a festival press release described it as "one of the first films to examine how mellifluously race, class, and role-playing morph into the social fabric of America.