If heroes and villains existed in the world of stand-up comedy, Tony Hinchcliffe would definitely be a bad guy. The Ohio native has gotten pretty good and picking people apart as a writer for the Comedy Central Roasts series, so crowds shouldn’t expect any mercy when he stops by The Sinclair on Sunday night. We caught up with Hinchcliffe to chat about his love of playing the heel and why he’s not afraid to perform pro-Donald Trump jokes.
What are some comedy lessons you’ve learned from your mentor and Boston University alum Jeff Ross?
He taught me to enjoy the process. The second where my competitive nature makes me uncomfortable, I take a step back now and remind myself I’m a comedian, young and should be having the time of my life. Jeff Ross is just a priceless mentor to be able to have over these years, not just as a comedian, but as a neurotic artist at all. This is a guy whose mentors are the great Buddy Hackett, Don Rickles, so the stuff that I’m getting is generational, Jedi knowledge.
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Which comic would you like to face the most in a roast battle?
I’m a better judge than I am a battler. The actual battling part is based on likeability, and honestly, I’m more of a villain. If I was cast in a movie, I don’t think I’d be the good guy. I’d be the Joker, a Bond villain or King Joffrey, even.
As a WWE fan, do you enjoy playing the heel?
Absolutely. 100 percent. I fully embrace it. It makes it more fun for me. I feel like the angles that I’m taking on a lot of my jokes are completely different than most stand-up comedians. I sort of go against the grain. I have some pro-Trump material, even though I’m not specifically pro-Trump. The material is. I’m pretty much looking at the positives of things. The evolution of my persona is definitely more heelish than ever before. That definitely derives from my fandom of professional wrestling.
Do you think Trump’s rise and popularity stem from a heel mindset?
Yeah. People want their hearts to flutter sometimes. They want to hear real talk. Sometimes it’s thoughts that everybody has but nobody wants to publicly say. When you take that angle of heel, you can write something different, angles that nobody could ever think of because some people are so used to wanting people on their side and wanting people to like them. By taking a completely different side of the spectrum, you can stumble across something. Those are my favorite jokes.
If you go:
Aug. 27, 9 p.m., The Sinclair, 52 Church St., Cambridge, $25, sinclaircambridge.com