Meet Watch Awards Talent Judge Wilson Cleveland

Unboxd founder sounds off on his favorite video projects

Actor and producer Wilson Cleveland has been in oodles of different projects, but he’ll never forget playing the world’s unluckiest vlogger in the season 5 premiere of BlackBoxTV.

The horror series webisode, titled How To Quit YouTube, told the part cautionary-part commentary tale of diving headfirst into YouTube culture.

“I'm really proud of it. It's so rare for an online series to maintain its audience for more than one season, let alone five, but I'd been a huge fan since the first episode and loved working with Tony Valenzuela. He's a good friend and a great director,” Cleveland told Adweek.

Cleveland, who also founded digital media and branded entertainment studio Unboxd, is one of the jury members for the talent section of the Adweek Watch Awards.

If you want to get on his good side, you’ll probably want to emulate some of the actors he thinks are killing it online. He cited his friend Milo Ventimiglia on Chosen and the cast of Wigs—which includes Julia Stiles, Virginia Madsen, Allison Janney, Josh Malina and Michael C. Hall—as some of his top favorites.

“I love seeing so many traditional film and TV actors doing digital projects,” he said. “For a scripted drama with a mostly female cast, that show did exceptionally well on YouTube but I've gotten into it a lot more since it's been on Hulu.”

Cleveland himself is best known for portraying Derek, one of the memorable characters on the Silicon Valley comedy Leap Year.

“Derek just wants people to like him so he seeks validation in all the wrong places which gets him into trouble,” Cleveland explained. “Over 2 seasons he's gotten himself sued, fired (twice) and blackmailed by Eliza Dushku's character, in the back of (a) pedicab no less.”

“He comes off as selfish but he means well and just wants to feel accepted as part of the team. He's flawed like every human, except he's not well-equipped to hide it,” he added. 

The Adweek Watch Awards will be accepting entries through April 14.