Jason Segel gets serious playing David Foster Wallace in The End of the Tour

Interview enough actors and you’ll start to hear certain tropes over and over again. Like how they were very shy as children. Or just how grateful they are to be in this project with that director. Another tried-and-true chestnut: They only want to take roles that push them out of their comfort zones. So when Jason Segel says, “I try to do things that scare me,” one could be forgiven for thinking he’s steering the conversation into well-worn territory. But talk to Segel for any length of time, and it becomes clear that fear — as an emotion, a concept, a tool — is something that preoccupies him. Scaring himself, after all, is what led him to write and star in 2008’s Forgetting Sarah Marshall (a project that he calls one of his most honest performances and includes what was surely a scary-to-film full-frontal nude scene); it was what helped bolster him when he decided to bring back our favorite felted figures in 2011’s The Muppets; and it’s what inspired him to write Nightmares!, the children’s book series about facing your fears. And it was that same mixture of angst and nerves that propelled him — less than 24 hours after ending his nine-year run as Marshall on How I Met Your Mother — to tackle the role of author David Foster Wallace in The End of the Tour (July 31).

His startling dramatic turn will stun audiences used to seeing Segel as a comic foil. The humor remains, but Segel goes darker than he ever has to transform into the complicated, conflicted, brilliant literary figure who committed suicide in 2008. Based on journalist David Lipsky’s 2010 book, Although of Course You End Up Becoming Yourself, the film focuses on the five days in 1996 when Rolling Stone sent Lipsky (played by Jesse Eisenberg) to accompany Wallace on his last book-tour stop in support of Infinite Jest, the critically acclaimed 1,079-page book that made Wallace a reluctant literary rock star.

Over the course of 106 minutes, the two men spar over everything from Alanis Morissette and cheeseburgers to talent, ambition, and depression — managing to forge a fragile intimacy in the process. It’s a career-changing performance for Segel and one that will surely start early Oscar chatter. “I watched the movie and I was so proud of him,” says Judd Apatow, who gave the actor his first break as Nick on the 1999 cult series Freaks and Geeks. “I could tell how deeply he related to David Foster Wallace and it all felt very personal to me. It made me cry.”

On a cool and rainy recent afternoon, Segel sprawls his long limbs over a sofa in New York City’s Bowery Hotel. In an industry where nearly every celebrity is essentially doll-size, the lanky 6’ 4″ actor is a towering anomaly. “I am right at the limit of being able to buy clothes at normal stores,” he says with a grin. “Anything taller would be trouble.”

Despite his size, Segel has an approachable, gentle-giant quality. “He has an inherent likability,” says The End of the Tour’s director, James Ponsoldt (The Spectacular Now), who’d been a fan of Segel’s since Freaks and Geeks. “Jason was the emotional anchor of that show. He was the one I felt like I knew — the one I wanted to spend time with. You watch early Tom Hanks, early Jack Lemmon or Jimmy Stewart performances — you just like hanging out with those guys regardless of the context or the film they’re in. I felt that way about Jason.”

While filming Tour in Michigan in the winter of 2014, Ponsoldt discovered many people felt the same way. “Jason is a very recognizable guy,” the director says. “If you’re on people’s TV sets several times a day, people think that they know you. Jason has a grace and kindness — it’s natural to him — but I think he works hard to be compassionate with people. I can’t imagine what it’s like to not be able to be alone in public.”

Segel, 35, has been acting since the age of 17 and recently figured out that he’s been in the public eye longer than he hasn’t. “I’ve made friends with it,” he says. “I figure out the parts I don’t like and I do my best to either eliminate those or acknowledge that I have no control over them.”

The End of the Tour explores one of the most tricky by-products of being famous: that total strangers bring their own ideas and expectations when they meet you. In the film, Lipsky arrives at his interview with Wallace with a set of preconceived notions — a bittersweet amalgam of admiration and envy — and Wallace is alternately amused, frustrated, and despondent at the disconnect between Lipsky’s idea of him and his true self. “There are certain things I could really relate to,” Segel says. “Specifically the idea that you never know the fundamental anyone. You know how you perceive them, but you don’t know what it’s like to sit in their skin at home when they’re alone at night.”

When Segel first read Donald Margulies’ script, he instantly loved it but wondered why Ponsoldt thought of him for the role. While he’s turned in quiet, poignant performances in smaller films such as Jeff Who Lives at Home, he’s still known mainly as the lovable lug in broad comedies like I Love You, Man and The Five-Year Engagement.

But for Ponsoldt — a hardcore David ­Foster Wallace devotee — it wasn’t a leap at all. “People who had a knee-jerk response to Jason being cast didn’t really understand who David Foster Wallace was. They knew he wrote a really challenging book and that he died tragically, so they assumed he must be a depressed intellectual,” he says. “Jason completely understands what it’s like to be open and vulnerable and honest with people who want a story from him. He gets it on a deeply fundamental level, what it is to live a creative life and to have your privacy feel stepped upon, and to try to find boundaries.”

To prepare for the role, Segel asked a few guys at his local bookstore to create an Infinite Jest book club; he listened to Lipsky’s original interview tapes; and he watched as much footage of Wallace as he could find. Then he left for the shoot’s Grand Rapids, Mich., location the day after he filmed the HIMYM finale.

Tour’s shoot was, by anyone’s definition, a bare-bones affair. “It really was just Jesse and me for 15 hours a day,” says Segel. “We drove to work together every day and would leave set, go to a drive-through or something, and then go to sleep and do it again.” It definitely made an impression on his costar. “It reminds me of the first movie I ever did, Roger Dodger — that good feeling, that camaraderie,” Eisenberg says. “We were in one of the coldest cities in America during one of their coldest winters on record, and I’ll remember this experience with that same fondness. A lot of that had to do with working with Jason.”

The movie came at a time when Segel was trying to figure things out careerwise, and it helped him focus. “I had arrived at a moment which is like, ‘Okay, if I’m lucky I have 60 more years of this. I better make friends with that other part of myself that either tells you that you’re doing great or you’re a piece of s—,’ ” he says. “We all have that Other Us that is with us at all times — you can’t get rid of that.”

Segel brushes off Oscar talk (“If Jason were the type of person that engaged with that too much, I think he might’ve been the wrong person to play the role,” says his director) and insists he’s just excited for the rest of the world to see Tour. “When they said, ‘That’s a wrap,’ I felt like I had done everything I possibly could to do my job well,” he says. “That’s a great feeling. My father asked me how things went and I said I did the best that I could. He said, ‘Oh, I’m sure you did better than that.’ I said to him, ‘No, I mean it in the right way.” He smiles. “I did the best that I could.”