Ri'chard appeared in films Coach Carter and House of Wax in 2005.[3] From 2006 to 2007 he had a recurring role in the CW series Veronica Mars and from 2009 to 2010 in the TBS sitcom Meet the Browns as Derek Porter, a buffoonish frat student who lived next door to Brown Meadows. He debuted in season 3 as a recurring character, and in the fourth season, was promoted to a main character. Ri'chard was set to star in a series entitled Eight Days a Week, starring Christina Milian and Mario Lopez on the CW Television Network during the fall 2007 season, but it was canceled due to the 2007 Writers Strike before airing. On November 16, 2011, it was announced that Robert Ri'chard was cast as Jamie in the CW series The Vampire Diaries.[4]
In 2015, Ri’chard played stripper in the comedy-drama film, Chocolate City.[3] He later returned to its sequel, Chocolate City: Vegas Strip (2017). In 2018 he starred in the erotic film, Kinky.[5] He later appeared in films Bolden (2019), Alone (2020) and Sweetwater (2023).[6] On television, he appeared in Lucifer and iZombie. He had the recurring roles during the final season of Fox soap opera, Empire, and the Amazon comedy series, Harlem alongside Cousin Skeeter co-star, Meagan Good.[7][8]