For the big screen, Hudlin expanded his thesis film into "House Party" (1990), starring the rap duo Kid N' Play (Christopher Reid and Christopher Martin). The low-budget comedy about 24 hours in the life of a grounded teenager who sneaks off to a big party earned praise for its realistic depiction of black life and its visual style. The success of the film, which featured the late comic Robin Harris as the teen's strict father, led to two sequels (which did not involve the Hudlins).

"Boomerang" (1992), starring Eddie Murphy, Robin Givens, Eartha Kitt and Halle Berry, was a successful romantic comedy about a womanizing marketing expert who meets his match in a predatory female executive. Later that year, the Hudlin brothers co-executive produced the animated musical comedy "Bebe's Kids", for which Reginald wrote the screenplay and provided three songs, based on the comic monologues of Robin Harris.

Working for the first time without his brother, Hudlin directed the satirical comedy "The Great White Hype" (1996), about a flamboyant boxing promoter (Samuel L Jackson) who arranges for a lackluster fighter (Peter Berg) to have a shot at the black heavyweight champion (Damon Wayans).

For TV, the brothers worked on the acclaimed HBO anthology "Cosmic Slop" (1994), which combined fantasy and social issues. Hudlin created the concept and directed the segment, "Space Traders", a parable in which space aliens offer to solve all the problems in the US in exchange for all the black residents. Hudlin also co-executive produced, wrote and directed the unsuccessful pilot "The Last Days of Russell" for ABC in 1995. Hudlin continued to obtain projects that called for him to utilize his acting and producing skills. His voice was used in the musical comedy "Joe's Apartment" (1996), as the character Rodney Roach. He then produced the 1998 comedy "The Ride", a feature about a group of young inner-city musicians who drive across country to be participant in a music video. After directing several episodic series, Hudlin put his focus back on the big screen directing the comedy feature "The Ladies Man" (2000) and "Servicing Sara" (2002), a feature comedy about a process server (Matthew Perry) who is convinced by a New York wife (Elizabeth Hurley) to serve her husband divorce papers.