Spears would next be known for taking a particularly stinging smack from Regina King while playing Cuba Gooding Jr.'s brother in the Cameron Crowe comedy "Jerry Maguire" (1996). That same year he began voicing characters on "C-Bear and Jamal", a Fox animated series featuring an inner-city protagonist, In 1997, Spears joined forces with John Leguizamo, another veritable whirlwind of comedic energy, for the feature "The Pest". 1997 also marked the beginning of Spears' run on the Fox sketch comedy series "Mad TV", a showcase for the performer's talent that would prove his skills and further his career considerably. His impersonations of such celebrities as Eddie Murphy, Tito Jackson, and most memorably James Brown added significantly to the show's appeal.
While starring on "Mad TV", Spears continued to work in film. In 1998, he was given the opportunity to play one of his own idols when he was cast as legendary comic Redd Foxx in the Frankie Lymon biopic "Why Do Fools Fall in Love". In 2001 he got laughs as "The Other Carson Daly" (as opposed to the white-bread host of MTV's teen scream-fest "TRL") in "Josie and the Pussycats" and co-starred in the college comedy "Higher Ed" as a chronic pot smoker who has a bad influence on his roommate (rapper-turned-actor Pras), a former burnout trying hard to be studios.