In the early 1990s, he formed a four-piece band called The Negro Problem which in 1995 released a box set collection of singles including an innovative cover of "MacArthur Park" and a multi-part pop operetta entitled "Miss Jones".
Solo career
He later went on to release albums under his own name. His 2000 release Guest Host was named Album of the Year by Entertainment Weekly and his 2002 album, The Naked Dutch Painter and Other Songs, repeated that feat. He toured in support of Love's Arthur Lee in 2002 and in 2003 he was invited to take part in the Lincoln Center's American Songbook series of concerts. Starting in 2004, he began writing the book, lyrics and music for his semi-autobiographical rock musicalPassing Strange, produced with the support of the Sundance Institute and The Public Theater, which won him the Drama Desk Award for Outstanding Lyrics. Also in 2004, he wrote and performed "Gary's Song" for the SpongeBob SquarePants episode "Have You Seen This Snail? ", which aired the following year. In 2006, he and Rodewald continued to produce Passing Strange as well as working on a film project with The Sundance Institute. Passing Strange had successful runs at the Berkeley Repertory Theatre in Berkeley, California, in the fall of 2006, and off-Broadway at The Public Theater in New York City during the spring of 2007. It received critical praise from both the New York Times and Variety and opened on Broadway at the Belasco Theatre in February 2008 under the aegis of producer Liz McCann and the Shubert Organization. The play garnered seven Tony nominations in 2008, with Stew receiving four nominations and winning the award for Best Book. The play closed in July 2008, with Spike Lee filming the final performances for a feature film which screened at the Sundance Festival in January 2009.
As Stew & The Negro Problem
Stew and Heidi debuted a new show, "Making It," at St. Ann's Warehouse in Brooklyn in February 2010. In December 2011, The Repertory Theatre of St. Louis announced that its 2012 new theatre series, Ignite!, would feature a reading of a stage musical adaptation of the graphic novel, Stagger Lee, with a book by the graphic novel's author, Derek McCulloch, and music and lyrics by Stew and Heidi Rodewald. He is current airing a live show and accompanying album titled Notes from a Native Song, inspired by the writings of James Baldwin, with Heidi Rodewald and members of The Negro Problem.