Jason Woliner Photo: courtesy of Adult Swim

Before YouTube existed, the writer/director had teamed up with Upright Citizens Brigade Theater dwellers Aziz Ansari, Paul Scheer, and Rob Huebel to make some videos. They were not officially a sketch group, nor were they Internet sensations. They were four guys with a handful of funny videos, like the Criss Angel-skewering Illusionators, that caught the right people’s attention at the precise moment before YouTube and Funny or Die democratized sketch comedy. As the main director of Human Giant, which ran on MTV for two seasons before ending on the creators’ own terms, Woliner had to figure out, on the job, nearly everything he would’ve learned in film school–like how to work with a crew that consists of more than one other person, editing technique, and just what a cinematographer does. He rose to the occasion and went on to establish himself as one of the handful of go-to names for directing TV comedy, as well as a writer and executive producer in his own right.

In advance of the latest special he’s co-written and directed, Dinner With Family, With Brett Gelman And Brett Gelman’s Family, which premieres February 13 at 12:30 a.m. on Adult Swim, Woliner talked to Co.Create about carving a path through TV comedy, the inherent honesty of a live audience, and how creative freedom must be earned.

Very few people start making truly funny films or shorts right out of the gate. In order to get really good at what he does, Jason Woliner had to be really not-so-good at it for a while–and learn from the experience.

“I think there’s such a supportive community in comedy right now, which is great, but I don’t know if that’s the right environment to be hard on yourself in,” he says. “I dropped out of college and ended up making this feature film I wrote when I was 19 with some friends. It was terrible. Making something that I saw was bad, though, and seeing all the wrong things that led me to that, is something I think is still valuable to this day. I made a lot of stuff I knew was bad right away, and I had to figure out why it was not working so I could make stuff that was better. It’s very easy to see something you make and say, ‘Okay, it’s good enough,’ but getting it from a place of ‘good enough’ to making it right is the step that makes things stand out.”

Human Giant Photo: courtesy of MTV, Viacom

After the amiable disbanding of Human Giant, Woliner worked as a director for hire for several years, launching pilots like Jon Glaser’s Delocated and overseeing a variety of sitcom episodes. Some of these opportunities came his way through MTV collaborators.

“We wrote together [on Human Giant], and it was important for me because I didn’t want to just be thought of as the director,” Woliner says. “It was important for me to write as much as everyone else in the group. [Show producer] Tom Gianas had a lot of connections in the comedy world and so these Conan writers would come by, pitch whatever sketch ideas they had lying around, and we’d write them together. From having met Jon Glaser there, a year later he asked me to do the pilot for Delocated. Jon Benjamin wrote and acted on the show and then we worked together later too. Human Giant, for me, was like directing school and comedy writing school at the same time.”