- Has worked with two Academy Award winning directors, Phil Alden Robinson and Mike Nichols, on the films Sneakers and Primary Colors, respectively.
- At the age of 19, in only his second stage production, he was cast as 30-something Brick in the first all-black production of the Tennessee Williams classic Cat on a Hot Tin Roof.
- Worked as a tour guide at Universal Studios Hollywood and later as a page at NBC Burbank.
- His stage production of "Section 8" was nominated for three NAACP Theater Awards; Best Production, Best Set Design and Best Supporting Actor (Darius Dudley).
- Wrote, produced and starred in Retiring Tatiana (2000) winner "Audience Favorite" of The Pan African Film & Arts Festival.
- Wrote, produced and starred in Section 8 (2006) winner "Best Feature Film" of the 2006 Arizona Black Film Showcase.
- Uncle Robert of Robert Winters and Fall fame recorded the 80s R&B classic "Magic Man".
- Father John Winters was a founding member of the 50s singing group The Pelicans who recorded the Doo Wop hit "Aurelia".
- Once moonlighted as a limousine driver and has the dubious distinction of having chauffeured three dead rock stars: Tupac Shakur, Kurt Cobain and Lisa "Left Eye" Lopez of TLC.
- First appeared on local television as a teenager on a Detroit dance show called "The Scene".
- While in high school he worked nights and weekends as an usher at Detroit's now demolished Norwest Theater.
- His stage production of The Devil and Billy Markham by Shel Silverstein, in which he produced and starred, was nominated for Best One Person Show (Local) at the NAACP Theater Awards 2016.
- Mother Ann Verlene Winters is a retired court clerk.
- Father John Clarence Winters played in the Negro League for the Kansas City Monarchs.
- After taking the Universal Studios tour with Winters as his guide, so impressed was actor/producer Leon Isaac Kennedy that he invited him to meet Penitentiary III director Jamaa Fanaka and was offered a role in the film which launched his professional acting career.
- His scene from a 1998 episode of WB's Smart Guy entitled Get a Job has gone viral on TikTok.
- He guest starred in the two-part series finale of ABC's Coach.
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