Bythewood segued successfully to off-camera creative pursuits working as a writer and producer on "A Different World" from 1991 to 1993, where he met his future wife, fellow filmmaker Gina Prince. Set at Hillman College, a fictional, predominately African-American university, "A Different World" offered Bythewood the opportunity to effect the ways in which blacks were portrayed in series television, a topic he would later address in his first feature, the Sundance-screened "Dancing in September" (2001). The writer-producer moved on to the Fox police drama "New York Undercover" in 1994, and stayed with the hard-hitting crime series with an exceptionally racially-diverse cast until 1997, when network pressure forced writers to kill off lead character Eddie Torres (played by Michael DeLorenzo) in order to make room for additional white characters in major roles. Bythewood next created the short-lived NBC action series "Players" (1997-98), a more lighthearted look at crime fighting.
Seemingly silent after his acclaimed screenplay for "Get on the Bus", Bythewood received his next big screen credit for Hi-8 footage contributed to his wife's celebrated directorial debut "Love & Basketball" (2000). His own debut came with "Dancing in September", a TV industry-set romance that paired an African-American writer (Nicole Ari Parker) with a TV executive (Isaiah Washington) who hit the jackpot with a network-pleasing series that is a realistic take on the black American experience. Unfortunately the honeymoon is short-lived, as the show is faced with cancellation if changes aren't made to the lead characters, changes that would make them the one-dimensional, stereotypical representations all too common on screens big and small. Dealing with many of the same issues as Spike Lee's more sensationalistic "Bamboozled" (2000), Bythewood went for the heart rather than the jugular with "Dancing in September", and proved a director with a skilled hand. Well-paced with a nice flow, Bythewood made the most of limited resources with this independent feature. Screened at Sundance in January 2001, the film made its debut on HBO the following month. Bythewood's career was on the ascent, and he snared the director's chair on a big-budget Hollywood project on which he shared story credit: DreamWorks' "Biker Boys" (2003), a high-octane action drama that played like a post-modern Western on wheels, featuring a host of African American professionals by day who take to the streets as motorcycle-riding desperados by night.