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Jason Segel Talks About Playing Author David Foster Wallace In 'End Of The Tour'

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David Foster Wallace won accolades for his 1,000-page tome “Infinite Jest” in 1996. Then he saddened fans by committing suicide just over a decade later. Actor Jason Segel talks about playing the late writer in the new film “End of the Tour."

Actor and writer Jason Segel first got on people’s radar in 1999 when he was cast in Judd Apatow’s TV show Freaks and Geeks. He cemented his fame in 2008 when he starred in and wrote the Apatow produced comedy Forgetting Sarah Marshall. Three years later he helped the Muppets re-establish themselves on the big screen with The Muppets, a new film musical about getting the Muppet gang back together. In it he got to sing the Oscar-winning song, Man or Puppet written by Flight of the Conchords’ Bret McKenzie. In 2013, he announced he was co-writing a series of young adult novels, the first one entitled Nightmares.

With The End of the Tour, Segel attempts his most serious role yet as late author David Foster Wallace. The film is based on the book by Rolling Stone writer David Lipsky and it focuses on the five day road trip the two men shared in 1996 during Wallce’s book tour for Infinite Jest. I spoke with Segel last month at the Hard Rock Hotel in San Diego.

JASON SEGEL: I had access to David Lipsky’s tapes from this interview, which was really helpful. What struck me most from listening to the tapes was, for as weighty as some of the moments were and some of the discussions, there are also five minute mundane conversations about what’s on the radio and that was really important taking into the movie because you need to want to be in the back of the car on this road trip with these two guys. And if it’s just two people talking smart for four days that’s not a trip I want to be on and luckily in listening to the tapes, it was the most interesting road trip I’ve ever taken part in.

CLIP When I think of this trip I see David and me in the front seat of the car, he wants something better than he has, I want precisely what he has already… David Wallace, welcome… Hi I’m David Lipsy… Hi… We only just met. He’s writing a piece on the tour. What’s this story about in your mind?... what it’s like to be the most talked about writer in the country… you’re a nervous guy… I’m all right how are you…

JASON SEGEL: So I listened to those tapes, I had some interviews I could listen to. He did Charlie Rose around the time of this story. And then I read, I read everything I could get my hands on and I think “Infinite Jest” informs the performance more than anything.

CLIP Isn’t it reassuring to have a lot of people read you… I think if the book is about anything, it’s about the question of why? Why am I doing it and what’s so American about what I’m doing

JASON SEGEL: I had read the short form non-fiction, like the “Supposedly Fun Thing I’ll Never Do Again,” and “Consider the Lobster,” which are as funny and insightful as anything I’ve ever read but “Infinite Jest” really did it for me. It’s a challenge, I mean it’s a thousand plus pages and it’s hard, and sometimes you want to throw that book against the wall if you’re perfectly honest but getting through it makes you feel smart, it makes you feel like you’ve accomplished something and that’s part of his intent is to remind you that you’re capable of this.

JASON SEGEL: I write as well, I’ve written a few of the movies that I’ve done and I write a series of books, nothing like “Infinite Jest,” and Jesse [Eisenberg] writes as well. He writes plays and he writes pieces for the New Yorker, we’re both writers, and one of the things that I think is interesting about writing is that it’s so much time alone, it’s so much time saying no I can’t meet you for dinner, you know for months. For me that’s months if it’s a screenplay or if it’s one of these children’s novels that I write. I have a partner and we work back and forth so we’ll work over three month bursts. To write something like “Infinite Jest” is years and years of saying no I can’t meet you for dinner. And it’s something that I think is probably pretty easily lost in the sort of romantic idea of writing a novel.

CLIP The more people think you’re really great, the bigger the fear of being a fraud is… David thought books existed to stop you from feeling lonely, those days with him reminded me of what life was like, and the conversation is the best one I ever had… It’s me talking to your recorder, I’m smoking, I said I wouldn’t smoke but I’m smoking and talking to your tape recorder…

JASON SEGEL: And it’s a very particular type of person who has that sort of dedication has that sort of discipline, can tolerate the loneliness and can also hold onto this idea that what I am writing is worth it. That people are going to want to read this and they are going to want to devote their attention to it. It’s a very particular personality type. And so I tried to bring some of that into it because I’ve experienced it. I think any artist is operating under the idea that what they are trying to express is worthy of people focusing their attention on and listening to it, hopefully you are right and if you are wrong, it’s a terrible delusion.

JASON SEGEL: When all you want to do is be part of the group but you are almost always if not always the biggest brain in the room, it’s a pretty tough thing. You know to be constantly aware of what everyone is doing, [repeats “doing” with air quotes] and just trying to be present is probably a tricky thing, your interior life is not matching your exterior life.

JASON SEGEL: It’s the interesting dichotomy of a writer is that you are constantly on the job.

CLIP You know what I would love to do man, I would love to do a profile on one of you guys who’s doing a profile on me, is that too cute? I’m sorry man, you’re just going to go back to NY and sit at your desk and shape this thing however you want and to me it’s just extremely disturbing because I’d like to shape the impression of me that’s coming across, I don’t even know if I like you yet. More interested in if you like me.

JASON SEGEL: The only way to counter your feelings of loneliness from the job is to be a part of something that you could never fully be in the moment with.

What was important for you to convey about him?

JASON SEGEL: Well I think there is a tendency to want to deify your idols or somebody like David Foster Wallace who spoke so beautifully to so many people. I think what’s really important about David Foster Wallace is he’s one of us.

CLIP If they are responding to your work and your work is really personal, reading you is another way of meeting you… that’s so good. I think if there’s a sadness for people under 45 it has something to do with pleasure and achievement and entertainment, a sort of emptiness at the heart of what they thought was going on… I have a serious fear of being a certain way. I treasure my regular guyness… people don’t crack open a 1000 page book because they think the author is a regular guy, they do because they think he’s brilliant…. What is with you… what is with you…I’m not so sure you want to be me. Just be a good guy.
JASON SEGEL: And I think that is what was really important to him and his writing is that if you read “Infinite Jest” or if you read his short form stuff too, it’s like someone saying hey, for the next 1000 pages or for the next ten pages, I am you. And allow me to sort of illuminate something that maybe you haven’t noticed or let’s talk about some things that maybe you didn’t even know that you were feeling. So I think one of the things that I really wanted to communicate is, this is one of us: flawed, brilliant, imperfect.

CLIP Can you do me a favor, can you tell me about that poster over there… Alanis?... Yeah… I don’t know, I guess I am susceptible like everyone else, why?... I mean she’s pretty… She is pretty. She’s pretty in a very sloppy, very human way. She has this squeaky, orgasmic quality to her voice, here’s what it is. A lot of women in magazines are pretty in a way that is not erotic because they don’t look like anybody you know. You can’t imagine them putting a quarter in a parking meter or eating a bologna sandwich whereas Alanis Morissette, I can imagine her like chowing down on a bologna sandwich and I’m absolutely riveted.

Do you think this film would be a richer experience if people had read his work or can you come to it cold and still appreciate it?

JASON SEGEL: It’s a really good question. I think the answer is both. I think if you know who David Foster Wallace is and if you know David Lipsky, it adds to the fun of the movie because you are sort of familiar with the themes but what I think the movie is really about has nothing to do with David Foster Wallace or David Lipsky. I think what the movie is about is this terrifying moment when things go as well as they can possibly go and you realize you still feel the same. And I think that’s a very universal moment. I think people arrive at it in their mid-thirties. Because in your twenties you are really working toward something, if I just get there, I am going to feel a certain way and you’re able to sort of work under the illusion that maybe I feel this way because I’m not there yet. And then finally in your mid-thirties you realize oh maybe there’s no there. And that’s the moment this movie is about.

There are some scenes where he directly talks about being a writer so as a writer yourself, did any of those scenes really click for you and hit a note of truth.

JASON SEGEL: There was one line that made me want to do the movie when I first read the script and it was now I have to face the reality, I’m 34-years-old and I’m in a room with a piece of paper. That’s before the book tour has even ended. That’s I think the reality of being a writer or any pursuit, any endeavor, as soon as you do the thing you’ve been trying to do, it’s time to do it again. Unless maybe you place your values someplace else.

One of the scenes that I thought was really effective was when he talked about jumping from a burning building. That was really strong, what was it like to do.

JASON SEGEL: It was scary. That was the second day of shooting. It was really interesting. It was, that was one of the most beautiful passages from “Infinite Jest,” that analogy, he talks really beautifully about depression in that book and another thing he says in that book is a girl is brought into a hospital after a failed suicide attempt and the doctor says why did you want to hurt yourself and she shakes her head and she says you’ll never be able to help me, you think I did this to hurt myself? I was trying to end the pain. And I think that it really informed the performance, it really spoke to me to that this was a man that this is a man that was willing to go to places that we try to suppress. Because I know that if you are watching this, you have had feelings in your own way that that relates to, this I can’t take it any more kind of feeling and I think you walk away from the movie with some interesting conversations to be had.

I had read that this is one of the screenplays that was highly rated as one of the best unproduced screenplays for a long time, why do you think it sat on the shelf for so long and why it might have been more attractive to be made?

JASON SEGEL: The script is written by Donald Margolies, an amazing writer, he’s won the Pulitzer Prize, I think a script like this probably sits on the shelf because it’s not a giant tent pole movie, there aren’t explosions, and that’s the kind of movie is profitable these days and I think that why a movie like this would get made now is I think that there is some reaction and I think there is a hunger for movies that serve a different artistic function than those movies, those movies are escapism and there’s definitely a great place for them, I like watching them, but I think that this serves a different function where you watch the movie and you walk away with whoever you saw it with and you go to dinner and talk. That’s a really important function of film, of art in general, and it’s really exciting to be a part of that.

And what are you most proud of in the film?

JASON SEGEL: I feel most proud of everybody involved gave everything that they had to the movie. That’s a really special thing when you’re working at this kind of budget and in these kind of conditions, it was Grand Rapids, MI in the dead of winter, it was 15 degrees, you’re doing it because you love it and it reminded me of being in high school thinking I want to do this someday and I’m gonna make it happen no matter what it takes, that’s what the process of mam=king this movie felt like and it was really special.

Thank you very much for talking with me.

JASON SEGEL: Thank you, it was my pleasure.

I’m Beth Accomando your resident Cinema Junkie, thanks for listening to my interview with Jason Segel about The End of the Tour. This week you can also find my review of the film on my new KPBS Cinema Junkie podcast. This is a new endeavor for me so please subscribe to the podcast on iTunes and give it a rating or send me your feedback on Twitter @cinebeth or on the Cinema Junkie Facebook page. Each week I’ll be reviewing new films and serving up new interviews or ones pulled from my 3 decades of archives. Check out Sir Ian McKellan talking about adapting Shakespeare or Simon Pegg discussing the pop culture references for Hot Fuzz. Satisfy your celluloid addiction with my Cinema Junkie podcast where you can mainline film 24/7.

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Cinema Junkie

Satisfy your celluloid addiction with the Cinema Junkie podcast, where you can mainline film 24/7. This film and entertainment series is run by KPBS Film Critic Beth Accomando. So if you need a film fix, want to hear what filmmakers have to say about their work, or just want to know what's worth seeing this weekend, then you've come to the right place