Gregg was born in Portsmouth, Virginia to parents Constance Gregg and Melvin Vaughan. He has six sisters. After graduating from I.C. Norcom High School, he studied marketing at Old Dominion University for 2 years before changing his career path and moved to Los Angeles in 2011 to pursue acting.
Gregg came to prominence by creating and sharing comedic content in which he starred, wrote, and produced on Vine. He amassed more than 7 million followers in the course of 3 years, becoming one of the top 100 personalities on the platform.
His first credited role was in the web series Whatever, The Series. in 2011 where he earned union eligibility. Following Vine’s decline in 2015, Gregg transitioned into film and TV roles. In 2018 he earned roles in the Netflix mockumentary series American Vandal and in the film High Flying Bird. Gregg's performance as DeMarcus Tillman garnered him praise from outlets such as Film School Rejects and a comparison from Live Mint to actor Will Smith in The Fresh Prince of Bel-Air. Entertainment Weekly and Vulture have described the role as a breakout one for Gregg.

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