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MAD REWIND with Brandee Stilwell

Brandee Stilwell

Ep 8: Orlando Jones on Creating MAD TV Legends, Cut Sketches, and Going Hollywood

Jul 1, 20261h 1m
Summary

In this episode of MAD REWIND, host Brandee Stilwell sits down with actor and writer Orlando Jones to reflect on his foundational experience as an original cast member and writer on MADtv. Jones shares his unique journey into comedy, tracing his roots from a public speaking champion in his youth to landing his first professional writing gig on A Different World while still in his teens. The conversation dives deep into the high-energy, unpredictable environment of the show’s first two seasons. Jones discusses his creative process for developing memorable characters like Dexter St. Croix and Ivan Hicks, emphasizing how his background as a sitcom writer helped him understand the specific cadences of his castmates. He recounts the chaotic joy of being part of the original ensemble, the challenge of navigating corporate networks, and the occasional friction that arose when his satirical sketches pushed too many boundaries. Ultimately, Jones provides a candid perspective on the complexities of being both a writer and a performer, explaining why he eventually moved on to pursue other artistic evolutions, proving that for him, the best is always yet to come.

Updated Jul 4, 2026

About This Episode

In this episode of Mad Rewind, host Brandee Stillwell sits down with the incredibly talented Orlando Jones! As an original cast member and writer for MAD TV's first two seasons, Orlando pulls back the curtain on the show's chaotic early days. He shares his incredible journey from writing for A Different World as a teenager to his wild 160-person audition for Quincy Jones.

We dive deep into the origins of iconic characters like Dexter St. Croix, Ivan Hicks, and Reverend Lamont Nixon Fatback. Orlando also spills the tea on the sketches that got cut (and got him called into a meeting with Bill Cosby), the real reason he left the sketch comedy world, and his seamless transition into blockbuster films like The Replacements. Plus, get the inside scoop on his magical first Comic-Con experience and the upcoming MAD TV reunion panel!

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