After high school, Wolfe enrolled at Kentucky State University, a historically black college and the alma mater of his parents.

In 1977, Wolfe gave C. Bernard Jackson, the executive director of the Inner City Cultural Center in the Los Angeles, the first scene of a play he was working on.

In 1990, however, Wolfe won an Obie Award for a best off-Broadway director for his play Spunk, an adaptation of three stories by Zora Neale Hurston.

After a Los Angeles opening, the play moved to Broadway, where it received 11 Tony nominations and won the Drama Desk Award for Outstanding Book of a Musical.

In the summer of 2006, Wolfe directed a new translation of Bertolt Brecht's Mother Courage and Her Children at the time Delacorte Theatre in Central Park, starring Meryl Streep, Kevin Kline, and Austin Pendleton.

Wolfe directed the film Nights in Rodanthe, starring Richard Gere and Diane Lane, which opened in theaters in September 2008.

Wolfe is bringing his artistic talent to the design of the upcoming Center for Civil & Human Rights in Atlanta as its new chief creative officer.

[3] In August 2017, Wolfe was the only one of the 17 private members of the President's Committee on the Arts and Humanities who did not sign on to a letter of mass resignation in the wake of Donald Trump's remarks on the Unite the Right rally incident in Charlottesville, Virginia.