A talented actor and writer who landed a host of career-making roles in the late 1990s, Orlando Jones got his start in the business with behind-the-scenes creative work on popular African-American sitcoms before gaining attention as a stand out member of the ensemble cast of Fox's irreverent sketch comedy series "Mad TV". Tall and thin, with remarkable onscreen energy and ease, the actor possessed intense malleable features that he used to good effect in both dramatic and comedic roles. Despite this gift, he surprisingly began his career with off-screen pursuits. Jones worked as writer and story editor for NBC's college-set comedy "A Different World" from 1991 to 1992. In 1992 he took a place on Fox's network roster working on the sitcom "Roc" as a writer and executive story editor. The series, following a working-class Baltimore family, would employ him until 1993 when he began working on the network's "The Sinbad Show" as co-producer and executive story editor.
Apart from a 1992 brief guest shot on the Fox sitcom "Herman's Head", Jones didn't appear before the camera until 1994, when, following the demise of "The Sinbad Show", he became a host of the daily music magazine series "Sound fX", on the Fox cable outlet FX. From there he landed a regular role on the especially irreverent sketch comedy series "Mad TV", where he took on such varied characters as laid back hip hop superstar Snoop Dogg, wacky sports celebrity Dennis Rodman and the more nefarious Ike Turner and O.J. Simpson to great comedic consequence. Additionally, fans of the series would undoubtedly remember Jones' flamboyant character Dexter, the scantily-clad drummer and musical director for the surrealistic talk show sketch "Cabana Chat".
While "Mad TV" offered the actor exposure and valuable experience, it was Jones' film work that would prove his versatility and endurance. In 1997, he lensed a featured role as a brush salesman caught in the crossfire of a vampire battle in "From Dusk Till Dawn 3: The Hangman's Daughter" (released direct-to-video in 2000). Supporting turns in "Sour Grapes" (as a homeless man embroiled in an outlandish murder plot) and "Woo" came in 1998, followed by an appearance in Mike Judge's live-action directorial debut "Office Space" (co-starring fellow former "Mad TV" cast member David Herman) in 1999. Later that year Jones went from one highly-anticipated ensemble drama to another, when was featured as a slightly sinister drug dealer in Barry Levinson's acclaimed "Liberty Heights", a drama set in turbulent 1954 Baltimore, to Paul Thomas Anderson's "Magnolia". In 2000, he took on roles in two sports-themed features set in the recent past in "The Replacements" (set during the 1987 NFL strike) and the mockumentary "New Jersey Turnpikes", a comedy following a fictional basketball team's struggle through the 1976 ABA-NBA merger. He was additionally featured in the star-studded comedy "Chain of Fools" that year, and teamed up with director Brett Ratner in developing "Sticky Fingers", a comedy feature about a thief, to star and be produced by Jones.
In 2002, Jones portrayed a band director (at the fictional Atlanta A & T University) out to prove that he has the best band/drumline that the historical black colleges and universities have to offer in the drama "Drumline," a feature loosely based on the life of music producer Dallas Austin. He then joined Laurence Fishburne and Derek Luke for the much anticipated motorcycle drama "Biker Boyz' (2003).