Wilson Cleveland: ‘Leap Year’ Co-Creator, Actor And The Hardest Working Man In Digital Video [#ProudToLove YouTube Series]


Wilson Cleveland is one of the most humble, yet prolific people working in digital media right now. Starting out as a film and television actor, Cleveland moved on from traditional television to carve out his own successful niche in digital video.

Leap Year” — a show Cleveland produced and acted in — refocused the common drama series paradigm of either 1) a show about rich guys being awful or 2) a show about the grunts working under those rich guys. Instead, the series shined the spotlight on a tech startup, a place where returns are rarely guaranteed, but when they are, they are massive.

Wilson’s character Derek in “Leap Year” also shifted that common digital drama series formula as the show subtly revealed he was gay in season two with little to no fanfare. Cleveland explains: “I wanted Derek’s sexuality to be a subtle layer to the character and not make him ‘the gay guy.’”

NMR caught up with Cleveland recently to talk about how digital media has influenced the Supreme Court’s decision to continue gay marriage in California and about the amazing, open community that is YouTube.

As someone working extensively in the digital medium, how have you seen platforms like YouTube influence the LBGT community?

Online video provides a platform for members of any community traditionally underserved by mainstream media to share their stories and voices with each other and the world. “Anyone But Me,” “Husbands,” Michael Buckley, Hannah Hart are just a few of the outstanding series and personalities to “come out” of the gay community and be enjoyed by millions online.

Do you feel as if digital video is opening new avenues for LBGT performers that would otherwise be closed in traditional platforms like film and television?

I feel digital video is opening new avenues for all creators and performers, gay or straight. Let’s be honest — there are plenty of gay men and women working in film and television just as there are in new media, but that doesn’t mean they choose to be open about it. Michael Buckley guest co-hosted ‘Live’ with Kelly Ripa not because he’s gay but because he’s incredibly talented and won a public vote by a landslide.

You have always seemed very open about your sexuality — have you found that this changes how audiences view you or your work online?

I don’t know if it changes anybody’s perception one way or the other. I don’t define myself by my sexuality but I don’t hide it either. I try to live my life as authentically as possible, and being gay is just one of many parts that make me who I am. That’s just my reality. As an actor I always look for the similarities between myself and the characters I play. When Yuri and I were talking about revealing my “Leap Year” character Derek as being gay, it was important to me not to make it some big plot twist or its own storyline. I wanted Derek’s sexuality to be a subtle layer to the character and not make him ‘the gay guy’ which is why we waited on the reveal until mid-way through season two.