As a massive comedy nerd, I was nervous about interviewing Donnell Rawlings for his latest show,Unchained, which he’s bringing to the Sydney Fringe in September. I’d been following the veteran comedian’s work since his days as Ashy Larry onChappelle’s Show, and was fully prepared to make an arse out of myself.

Despite my trepidations, what ensued was one of the funniest conversations of my life, including everything from the “Great Barrier Reef getting shit on” to his unique and hilarious comedic beginnings.

“I used to go to comedy clubs with my co-workers and I started as a heckler. I was the guy who was trying to take the piss out of you,” Rawlings laughs. “I started to build an audience and a following and people would be like, ‘Is that asshole guy going to show up? Because he was funny last week.’ Eventually, I was challenged to go onstage and what they thought was going to be a horrible show turned out to be a good one.”

So basically, Rawlings got his break by being a jerk to people? He laughs and replies, “You don’t know the level of jerk I was. Before I’d even told a joke I tried to work a door deal with the club. I was like, ‘Listen, there has to be a fee for somebody being a jerk at the level that I am.’”

Rawlings continued to take chances in order to establish his career as a comedian. “The first television show that I did was Def Comedy Jam. A friend gave me this business card for the talent executive of the show. So as the cocky person that I am, when the receptionist answered the phone I acted like I’d known the dude for 20 years,” he laughs. “When she answered I was like, ‘Where’s Bob? Put Bob on the phone. Is Bob there?’ She was so nervous and scared that I was somebody she was like, ‘Oh I’m sorry, one second!’ Two weeks later I was performing in New Jersey and my friend told me that I’d booked Def Comedy Jam.”

Besides scaring the shit out of administrative staff, Rawlings says he doesn’t have a specific brand when it comes to his comedy.

“If there’s something that happens in pop culture that’s really relevant, something that’s excited me about politics or something that upsets me about race, I’ll try and put my spin on it. I think that comics are the best people to take you to a place that you wouldn’t normally go, or you’d be afraid to go to. One of the beauties of working on Chappelle’s Show was that we talked about racial issues, but we did it in a funny way. You can laugh people into anything. I don’t consider myself to be a preacher, but with my style of comedy I want people to leave with some kind of message.”

This idea is certainly relevant for his latest show title, which was inspired by Quentin Tarantino’s Django Unchained.

“The movie is about a guy that’s breaking away from the norm, breaking tradition and going to avenge something because he wants to prove a point. For me, that title just resonated with what I do. I’m an outspoken person, I want to take chances and I want to break away from what you think is normal. How do you do that? You gotta break the chains.”

Unchained, as part of Sydney Fringe Festival 2014 atGiant Dwarf Theatre, Redfern onWednesday September 17, tickets online.

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