Wilson Cleveland

In 2006, Cleveland created and starred as the character Nick Chiapetta in The Temp Life, a comedy web series which debuted on YouTube on November 29, 2006 and ended January 24, 2011 after 5 seasons. In 2012, The Temp Life won the Webby Award for Best Comedy Series.

In 2011, Cleveland executive produced an 8 episode web series called Bestsellers. Cleveland created, executive produced and starred in Suite 7, a seven-episode branded web series sponsored by the Better Sleep Council and distributed by Lifetime.

Cleveland is the co-creator, executive producer and co-star of Leap Year, a comedy-drama series about five former co-workers starting a tech company in Silicon Valley, that aired for two seasons on Hulu from 2011 to 2012. It was revealed during the second season that Cleveland's character, Derek Morrison is gay. Cleveland, himself openly gay, explained in a June 28, 2013 NewMediaRockstars interview, "I wanted Derek’s sexuality to be a subtle layer to the character" and "not make it some big plot twist or its own storyline." In 2013, Leap Year won the Webby Award for Best Branded Entertainment (Scripted), the Streamy Award for Best Branded Series and the IAWTV Award for Best Dramatic Series.