Gregory has hosted several events, such as the BET Anniversary and Achievement Awards with Debbie Allen and Shirley Moore, the Black Stuntwomen Beach Competition, and the Elite Lee Jeans Model Look with Roshumba Williams and Angelica Bridges. He has also hosted a radio show on black writers, supports minority filmmakers, and appeared at high school dedications to support better educational opportunities. He is a founding member of Epiphany Theater Group, established by writer/producer/director Bill Duke. In 2010, Gregory made an impromptu appearance on The Tonight Show with Jay Leno in the "Jaywalking segment". Jay Leno was apparently unaware of who Gregory was until Gregory informed him.
