1. TBT

How Jason Segel landed a plum role

For years, Jason Segel has proved himself a reliably funny dude, a comic foil and sometimes-leading man in rom-coms, brom-coms, and a sitcom, too. Knocked Up, Forgetting Sarah Marshall, I Love You Man, The Five-Year Engagement, and nine seasons' worth of the CBS hit How I Met Your Mother —the guy's comedy cred is without question.

But Segel was itching to try something different, something with more heft, more meaning.

Few projects have more heft and meaning than playing David Foster Wallace, the author of the 1,079-page Infinite Jest, a novel full of endless endnotes and encyclopedic digressions that brought the American writer huge acclaim. Wallace was a lumbering, self-deprecating guy, a double major in English and philosophy, a dog lover, a depressive. In 2008, at age 46, with two novels and three short story collections to his name, he hanged himself on the patio of the California house where he lived with his wife.

In The End of the Tour, Segel plays Wallace in the winter of 1996, just as Infinite Jest — a book about addiction, recovery, family, language, science, identity, tennis, and truth — was published and he embarked on a series of readings around the country. David Lipsky, a writer for Rolling Stone, talked his editor into a Wallace profile. For five days, the journalist tagged along, recording their conversations in cars, planes, diners, and hotels.

James Ponsoldt's film is based on Lipsky's book, Although of Course You End Up Becoming Yourself, which was published after Wallace's death. Jesse Eisenberg stars as Lipsky. The heart of the film is the back-and-forth between the two men, transcribed from the original cassette tapes.

"I got the script sent to me," says Segel. "I was about to get on an airplane and it arrived, and I read it on the plane. And when I landed, I called my agent and said, 'Look, this is a beautiful script, but they're never going to let me play this part.' And she said, 'No, James Ponsoldt wants to talk to you. I think he is thinking about you for it.' ''

So Segel and Ponsoldt talked. The actor asked the director what gives, why me? The director brought up Freaks and Geeks, the short-lived NBC sitcom Segel was in for its 1999-2000 season. Segel says Ponsoldt told him that "even when you were doing comedy, I thought I saw something sad behind your eyes." It was a quality Ponsoldt thought essential for anyone who was going to portray Wallace.

"I think what was important about David Foster Wallace is that he was one of us," Segel says. "James didn't want to do a movie where (Wallace) felt like something other than us . . .. He wanted it to be somebody who was in the trenches with us who happened to be gifted with an amazing vocabulary.

"It's the same way you feel about Salinger when you read Catcher In the Rye in high school. You're like, 'Whoa, this guy is able to express that feeling that I've been trying to express but all I've been capable of is, 'Get out of my room!' ''

As he prepared to play Wallace, Segel listened to Lipsky's tapes. He studied recordings of Wallace lectures. And, of course, he read Infinite Jest. It took him 10 weeks — 100 pages a week, and a group of friends to discuss what they'd just read. "Accountability is helpful," he jokes.

What Segel didn't do, though, was talk to Lipsky.

"I made a conscious decision that it was really important not to hear too much from David Lipsky about his thoughts on David Foster Wallace or there would be no tension in the film. Because both Jesse and I would both be playing David Lipsky's perspective. Do you see what I mean? Jesse playing David Lipsky and me playing David Foster Wallace as seen by David Lipsky — and there goes the tension."

And tension there is, aplenty. Professional jealousy (Lipsky's), professional and personal doubts (mostly Wallace's), a fear of presenting oneself as smarter, more talented, above the fray (Wallace, definitely).

"A lot of the scenes are Jesse and I alone together, Segel said. "And it's interesting, because sometimes they're getting along and sometimes they're not. It's a little like playing a friendly tennis match, in that you need each other to keep the volley going, but you also want to win the points. And so there's some question of how long am I going to volley with this person before I lay the smackdown?"

Wallace was 34 at the time captured in The End of the Tour. Segel was the same age when he and Eisenberg and Ponsoldt were filming. Yet, the suicide that loomed ahead of Wallace back then was something Segel couldn't help but consider.

"I've learned that trying to guess what's in somebody else's mind is not a good idea," Segel says. "But I do think that if you read Infinite Jest, he writes very eloquently about suicide and depression. And, you know, honestly, everything I felt like I needed to learn about David Foster Wallace during this period I learned from Infinite Jest. I felt like even though it was fiction, it was just incredibly personal.''