Troupe is the son of baseball catcher Quincy Trouppe (who added a second “P” to the family name while playing in Mexico to accommodate the Spanish pronunciation “Trou-pay”). As a teenager in 1955, he recalled hearing Miles Davis at a St. Louis, Missouri fish joint, where some fellow patrons identified the 78 rpm juke box record as “Donna” which was Davis’ first recorded composition (The record is most likely to have been the Charlie Parker Quintet session recorded for Savoy Records, May 8, 1947).

When he returned to civilian life, Troupe moved to Los Angeles where he became a regular presence at the Watts Writers Workshop and began working in a more jazz-based style. It was on a tour with the Watts group that he first began his academic life as a teacher. The Watts Writers Workshop was located in a building that also had a theater, allowing members to do readings, workshops, plays and presentations. It was a meeting point for many in the Black Power movement, Black Arts Movement and the civil rights movement and through it Troupe met many individuals involved in other cities including Ishmael Reed (Umbra Group), James Baldwin. In 1968, he edited the anthology, Watts Poets: A Book of New Poetry and Essays.

According to the Poetry Foundation, his work is associated with Black Arts Movement writers such as Amiri Baraka, Nikki Giovanni, Wanda Coleman, Haki Madhubuti and Ismael Reed, who were also friends. Their work was diverse but was strongly informed by world literature and jazz music. Some time later it emerged that the Workshop had been a target of the covert FBI counterintelligence program COINTELPRO, and that the Workshop, along with its theater were burned to the ground, in 1973 by the FBI informant and infiltrator, Darthard Perry (a.k.a. Ed Riggs). It also emerged that Riggs had not only been sabotaging equipment at the Workshop but also used his association with it to infiltrate the Los Angeles chapter of the Black Panthers, and numerous other organizations that promoted black culture, ultimately being instrumental in their demise.

In 1985 Spin magazine hired Troupe to write an exclusive two-part interview with Miles Davis, which led Simon & Schuster to him as coauthor for Davis’s autobiography.

Miles: the Autobiography was published in 1990 and won an American Book Award for the authors, garnering them numerous positive reviews and accolades.

From 1991 to 2003 Troupe was professor of Caribbean and American literatures and creative writing at the University of California, San Diego, in La Jolla, California.

On June 11, 2002, Troupe was appointed California’s first poet laureate by then Governor Gray Davis. A background check related to the new political appointment revealed that Troupe had, in fact, never possessed a degree from Grambling; he attended for only two semesters in 1957–58 and then dropped out. After admitting that he had not earned a degree, he made the decision to resign, rather have it become a political issue for the Democratic Governor. As a consequence, he resigned from the poet laureate’s position in October 2002 and retired from his post at UCSD.

The year 2006 saw the publishing of his collaboration with self-made millionaire Chris Gardner on the latter’s autobiography, The Pursuit of Happyness. The book served as the inspiration for a film of the same name later that year starring Will Smith.