Leon appeared in a 1989 episode of the NBC series Midnight Caller, in which he played an athlete who falls victim to crack cocaine.

Leon's early film roles included a football teammate of Tom Cruise in All the Right Moves (1983) as Shadow Nading, and the Notre Dame-bound basketball-playing co-worker of Matt Dillon, in The Flamingo Kid (1984).

That same year, he co-starred as John Lithgow's henchman in Renny Harlin's Cliffhanger and followed with a turn as a disillusioned ex-jock in New Line Cinema's Above the Rim (1994).

Leon also appeared as Lela Rochon's married lover in 1995's Waiting to Exhale directed by Forest Whitaker and starring Whitney Houston.

He co-starred as "Stoney", best friend of Joaquin Phoenix, in Miramax's military drama Buffalo Soldiers and had an uncredited role as "Joseph 13 X" in Michael Mann's award-winning biopic, Ali, starring Will Smith.

These tours were of Friends and Lovers (2005), based on Eric Jerome Dickey's New York Times bestselling book; of 3 Ways to Get A Husband (2009 and 2010), as a soldier returning from Iraq, co-starring Billy Dee Williams; and the revival of Why Do Good Girls Like Bad Boys (2012).

Leon and the Peoples' single "Love Is A Beautiful Thing'" was featured on the BET/Centric TV show Culture List, which premiered on July 21, 2013.