Chris Messina is used to being the “nice guy.” From portraying the lovable-but-curmudgeonly OBGYN Danny Castellano on The Mindy Project to the Republican lawyer who wins Claire’s heart on Six Feet Under to the sweet husband in Julie & Julia, the 44-year-old actor has built a career on his heart-stealing roles. But Messina admits he’s been looking for more challenges after more than 20 years in the entertainment business. His latest character, for starters, is quite the departure from his typical roles: In Jean-Marc Vallée’s HBO adaptation of Gillian Flynn’s debut novel Sharp Objects, he plays outside investigator Detective Richard Willis, who finds himself in Wind Gap looking for Natalie Keene’s murderer while also uncovering the Missouri town's violent past.

In person, Messina looks more like a world-weary musician, clad in a black-and-white Bob Dylan screen-print t-shirt (he bought it at a Seattle music museum) sans the sweaty button-down he sports on his current series. “I was actually looking for a Nirvana shirt,” he says. “I feel like you need a Nirvana shirt when you’re in Seattle, but they didn’t have my size. Can’t beat Dylan. How can you not like Dylan?”

In conversation, Messina speaks humbly about his success in his raspy Long Island accent. On a rainy morning on the Lower East Side, GQ talked to him about his role in Sharp Objects, why he’s a “dinosaur” when it comes to technology, and how he ranks the Hollywood Chris’s.

GQ: You’ve been acting for the past 20 years. Is that always what you wanted to do?

Chris Messina: My mom was a dance teacher, so I danced as a kid. I wanted to be Baryshnikov. Obviously I didn’t have that skill or talent, and in high school, I found there was a theater class and English credit I had this incredible teacher where we did all these improvisational plays about sex, drugs, and rock ‘n’ roll. It was really progressive in high school, and I fell in love with it.

When did you feel like you had your big break?

I feel like I still haven’t had my big break. Six Feet Under definitely was a nice moment for me. I come from New York Theater where I did plays uptown in the Bronx or in the Lower East Side and a lot of off Broadway stuff. A lot of stuff no one saw. I was on the last season of Six Feet Under. That was a beloved show, and that job really helped me. Since I played the Republican nice guy lawyer, I was kind of trapped in the nice guy suit which was difficult to break out of, which was a blessing and a curse, but I’m very grateful to Alan Ball for letting me play that part. When I was in New York, I was playing so many complicated characters, so when I got a Republican lawyer my friends here were like, “What?” But then if you do something decent in Hollywood, they want you to keep repeating it over and over again. It’s been a quest to show other sides, but I think that’s the plight of every actor, constantly being, “You don’t know what I can do, and you don’t know me. I can go here and I can go there.” It’s the frustration of it, but the fun of it too: pushing yourself and scaring the shit out of yourself, trying things even you don’t know what you can do but taking big swings.

Richard Willis is a departure from your “nice-guy” roles over the years, though. How did you prepare for and approach playing someone more rough around the edges?

I read the book, obviously, which is awesome. [Gillian Flynn] is a fantastic writer. It was pretty clear from the book what I needed to do and what my job was—very cinematic storytelling. I met with a bunch of police officers and detectives and did a lot of ride-alongs. It was really important for me—because you don’t find out too much about Richard—to come to Wind Gap with a lot of his own baggage. I kind of saw him as the other side of the coin that Camille is on. He’s not as severely damaged as she is—or in the same kind of pain. But he has pain. He’s an outsider. He’s lonely, and I think his heart has been broken and shattered. I think he wants to be seen and heard. So I think it was important to come to the story with my own skeletons in my closet because a lot of people have skeletons in their closet in the show. The scripts were so good, and when you act opposite Amy [Adams], Patricia [Clarkson], Elizabeth [Perkins] or any of them, my job is taken care of because they’re so good that I have to shut up, listen, and respond to them.