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Who plays rec center boss Theo on Will & Grace? Derek Gaines is a successful comedian with plenty of TV and movie roles

Derek Gaines
Derek Gaines, seen here on MTV’s show Broke A$$ Game Show, is guest starring on Will & Grace. Pic credit: MTV

On tonight’s episode of Will & Grace, Derek Gaines will guest star as Jack’s rec center boss. During the episode, Jack, played by Sean Hayes, will get into a fight with Gaines, who plays the role of Theo.

This isn’t the first time that Derek is appearing on Will & Grace. He also played the role of Theodore back in 2017 on an episode called How To Succeed in Business Without Really Crying. On his Instagram Live, Gaines shared the news of his role on Will & Grace last night, revealing he was coming back to the show as Theo.

Derek Gaines is from California, but he grew up in Philadelphia. This is where he started exploring comedy.

According to his personal website where people can find dates for his upcoming comedy shows, he is currently living in New York City, where he’s often on stage, performing comedy shows and filming television and films.

His first break came in a comedy competition called Bill Bellamy’s Who’s Got Jokes in 2010. At the time, he reached the finals.

That same year, he was also a finalist in Philadelphia’s Funniest Competition. But it wasn’t until four years later that he got in front of the cameras for the AXS TV’s Gotham Comedy Live, which you can find clips from on YouTube.

His hilarious sets and his relatable personality landed him work on Just For Laughs and various MTV shows, such as Broke Ass Game Show, and Joking Off.

According to IMDB, Derek believes that God has given him the gift of comedy, something he doesn’t hide. And while he worked hard to get where he is, working through Pennsylvania, New Jersey, and New York with his comedy shows, he has still completed several years of education.

Derek attended the Overbrook Regional Senior High School and graduated in 2002, and then graduated in 2005 from the Camden County College.

In 2013, he starred as Mike Watts in What Would Dylan Do, which is a TV movie. In 2017, he starred in Training Day, a television series.

Other than Will & Grace, he’s also worked on Relatively Happy, another television movie, and the TV series, The Last O.G. Here, he had a more prominent role, playing Jaybird for 8 episodes.

He just wrapped a short called Yous Got Somethin’, Right There, alongside Sydney David and Shane Gillis.

As for Derek Gaines’ personal life, little is known. He seems to keep his family and personal relationships out of the spotlight. His social media profiles are dedicated to his acting and comedy career.

Will & Grace airs on Thursdays at 9/8c on NBC.

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