Interview: James Ponsoldt On THE END OF THE TOUR And Why He Needed To Make It

In the cinematic universe, James Ponsoldt is the Johnny Storm of emerging directors -- he's on fire. (That is a nerdy -- and perhaps, awful -- comic book reference. If you don't read comic books, just ignore me and know what I mean is Ponsoldt is now a go-to director for cinema.) His first film to premiere at Sundance was tender and touching movie called Smashed, starring Mary Elizabeth Winstead (whose career is flourishing fast and furious) and Breaking Bad's Aaron Paul. This film was the catalyst that set his career as a prominent filmmaker in motion. 

Every film Ponsoldt directs now turns into gold. He's puts all the heart and soul he has into every film. Currently in theaters is his latest, The End of the Tour (our review here), about the late author David Foster Wallace's brief relationship with journalist and author David Lipsky. 

It's an effective and potent observation on the fear of loneliness, and comedian Jason Segel mesmerizes as Wallace. As you'll read in the interview below, I had to keep reminding myself this is the same guy whose career started out as "Watermelon Guy" in Can't Hardly Wait, then he went on to co-star in Judd Apatow comedies and Freaks and Geeks, and made The Muppets relevant again. In short, Segel has come a long way and I hope he's enjoying all the love he deserves and is currently getting.

I saw Smashed at Sundance (review here) when it premiered, and since then Ponsoldt and I have remained in touch through social media. After seeing The End of the Tour, I had so many questions I needed answers to. So I reached out to Ponsoldt on Twitter and asked if we could do an interview. Without hesitation, he said yes and we planned a time. 

Little did I know he would be doing this on his personal time while on break from shooting his new film The Circle, starring Tom Hanks, Emma Watson, John Boyega (and from my understanding, more casting announcements will roll out soon). Ponsoldt is now a very in-demand filmmaker and hasn't lost his cool -- he took time to speak to a journalist when he's busy busy busy which says so much about his character. He's a rare breed.

I was going to introduce you to the two Davids in the film (played by Segel and Jesse Eisenberg), but Ponsoldt does a really good job of doing that himself. This is a very long interview and that's because Ponsoldt is super passionate about each film he does. The End of the Tour is already out and even though he's currently in the process of a new film, he's still taking time to talk about his previous work. That's crazy cool of him. A rare breed, I tell ya.

Grab a chair, sit down, read this interview and learn how a filmmaker genuinely discusses questions from a journalist asking them. He's a sweet man who knows what he's doing, who knows what he's saying, and most importantly, who knows what he's making.  

Hello?

Hey Chase. It's James Ponsoldt.

Hey, what's up, man?

Hey, sorry I'm calling two minutes late. My apologies.

No, no. No worries. I just glad we can do the interview. Thanks for taking some time out of your busy schedule to talk to me.

Thank you for taking time out of your busy schedule. I really appreciate it.

Oh, you got it, man. Well, cool. Well, I know you're about to get ready to shoot a super awesome movie [The Circle], so let's go ahead and jump into this.

All right. (Laughs)

Something that really fascinates me about all of your films, they deal with alcoholism in one way or another, and I'm curious about the reasoning behind that.

Well, in the case of The End of the Tour, addiction wasn't a motivating factor in doing the film. Honestly it started with my former play-writing professor, Donald Margulies just writing me an email and saying, "Hey, James. I don't know if you're a David Foster Wallace fan or if you've read this book by David Lipsky, but I've adapted it. We'd love for you to read the script." 

He has no idea ... He's was my professor 15 years ago, and we've stayed in touch, but he didn't know that I was a life-long David Foster Wallace fan, and that yes, I had in fact read David Lipsky's book pretty much the second it came out. So that was really the catalyst for it. It wasn't a preconceived notion about addiction or mental health or anything like that. That relationship and my love for David Foster Wallace, who is obviously a very, very complicated guy in many ways, with his personal life, creatively, and et cetera.

Yeah, yeah. Sorry. Maybe I wrote ... I meant all of your films, THE SPECTACULAR NOW, SMASHED, and the first one that I've forgotten the name of, with Nick Nolte -

Off the Black.

Yes! Just about alcoholism -- which they all have in them in some way -- and I'm just curious the reasoning behind that, or did it just happen?

Again, in the case of the The End of the Tour, it was a funny thing. I did think when I decided I was going to make it would just be construed as part of a larger thematic of films that I'm doing, but at the end of the day, I was like, "Well, honestly I could care less in that regard how it's construed. It was like I love the story. I have deep love for the characters and David Foster Wallace. Yeah, it's kind of one of those things. I imagine if I'm lucky enough to keep making movies, there will be characters who probably wrestle with any number of demons which I couldn't possibly predict. There's nothing premeditated, I guess sort of to say, on my part. I need to tell stories of characters who wrestle with one thing or another.

As far as my own life and the people around me, I have many, many, many people in my life who've wrestled with all types of issues of addiction. It's definitely not something foreign to me, and as I get older, it seems that everyone has their sort of demons that they wrestle with. I don't know many people that have reached ... I'm 36 now. I don't know many people that have reached this age without wrestling with something, or at least someone, if they are one of those fortunate few, then someone who's very, very close to them wrestling with something like that. It just seems very common. I don't know. I guess in a large sense, I like to depict the lives of real people as I know them in all of their reliability.

Yeah, that's what I was going to say is that's one of the many reasons why your films are so great and wonderful because they are relatable, and it helps people who are dealing with addiction in some ... Any form of addiction that you're not alone, and that's what really resonated with me with SMASHED, because I've had -

Oh, thank you.

- issues with drinking and this and that, and it just really inspired me to try and get my shit together.

Oh, thank you.

You got it.

Yeah, no it was ... Smashed was a really deeply meaningful film for me to make, and it was sort of started in writing that script with my friend Susan [Burke] who had very, very directly dealt with those issues. Then for myself, it had been sort of a recognition ... This was years ago, but I think it was my third wedding in a year where I realized that the bride and groom were both needing to almost be carried out of their own wedding. I just realized, wow, I have so many friends that have addiction issues, and it's really, really, really funny, in a way, from a distance until it's your life, your spouse, your parent. It gets very real once you start having kids and you begin a cycle, and honestly the cycle had probably began before you.

It's funny you mentioned Susan, because when I was living in LA, I actually reached out to her and let her know the screenplay really meant a lot, and we actually met up and talked about that -

Oh, that's fantastic.

- about her past and everything. Yeah, we've become friends because of you. So thank you.

Oh, oh man. No, thank you. That's actually the most beautiful I can think of that a friendship would have come out of a film that I got to work on. In my book, it doesn't get much better than that. Susan is one of the most beautiful, radiant people I know, just so funny, and wise, and genuine, and selfless, and really, really courageous, I think.

Pretty cool.

Yeah, that's great.

Thank you. Yeah. Sticking with addiction, I spoke with Bobcat Goldthwait yesterday - 

Oh, wow.

- about addiction. He went through a lot of struggles. I know Jason Segel has had some issues in the past, and he spoke very candidly about it on Marc Maron's podcast not too long ago, and how the role couldn't have come at a more perfect time. Did his past struggles come with caution tape before casting, or did you feel safe he was in the right mindset to do it? I feel like the role was very therapeutic for him and helped clear his mind even more, which is ironic, because that's the opposite of the character he's playing.

Yeah. Jason was ... It's interesting, and I thought that ... I love Marc Maron's podcast, and I especially think that episode with Jason is a really incredible one. It was interesting. Jason told me ... I guess they tape that about a week before it airs, and so I happened to be with him the night that he had recorded that thing earlier in the day, and he told me what had come up on it. Jason has been very candid with me from the first time we met about things that he struggled with personally that he didn't, at that point, talk about publicly.

It's an interesting thing. Jason ... Freaks and Geeks for me came at the tail end of my time in college. Infinite Jest during my freshman year, Freaks and Geeks came out, I think it was my junior or senior year. As far as things that I was consuming, as far as entertainment, books, television shows, et cetera, I felt Freaks and Geeks was really, really impactful for me. I thought it was one of the most beautifully cast teen ensembles I had ever seen. 

That, along with My So-Called Life and The Last Picture Show, American Graffiti, Fast at Ridgemont High, Dazed and Confused, and Segel ... There's so many phenomenal actors that came out of that show, and Jason was the emotional anchor of that show for me. I really loved him on that show, and I was thrilled when Forgetting Sarah Marshall came out, it was a show I really, really like. It was notable to me that Jason had written that script, and then he continued to write scripts. He was the guy that he wrote the Muppets film in addition to starring in it. He's got his second children's book coming out that he wrote.

There's something, as you know as well as anyone, the process of writing - the very, very humbling, lonely, isolating process of writing and having to choose to commit yourself to hours and hours and hours and hours of being alone and saying "no" to other things, and trying to get your ideas down on a page, and then never being exactly what you want them to, except for maybe like 1% of the time, and then forgetting that writing to the scrutiny of others who might be really brutal and judgmental - it usually does one of two things. 

It either makes someone double down, develop a thick skin, and know that they're a writer, and they're kind of addicted to it and can't not be, or they quit. Jason just has internalized that, and the roundabout way of saying when I actually did meet him, I didn't know him before this film, but when I did meet him and we really started to get to know each other and trust each other, and as I learned more about him, a lot of things really clicked about who he was, which was ... 

I'm stating the obvious, but he's very different than the person he was on the sitcom that he was on for nine years. Just like Tom Hanks is different than the character he played on Bosom Buddies. You go down a list of actors that came from TV, but Jason's just a remarkably bright, complicated, empathetic, and thoughtful person. When you speak he really listens. 

He tries to be present, and he seems ... At the point that I met him, which was ... I met him the fall before we shot the movie, so I met him in fall of 2013, I guess. He just seemed like someone who was really grateful, who's really taking stock now in his 30s of how he's lived with that 10 or 15 years of his life, and wanted to do something honest and brave. I just have deep admiration for him, and really continue to. In my experience with him, he's just been consistently a really kind and thoughtful person who works his ass off.

Yeah. I love it when a comedian takes on drama, because it's a hard transition and needs to be believable. Jason Segel as David Foster Wallace isn't only believable, he completely embodies him, and just like ... I kept having to remind myself when I was watching the movie, "that's Jason Segel!" That's amazing, and he just deserves all the love that he's getting for the role. He did a wonderful job.

Yeah. He's a really fantastic actor. This is a ... Honestly, I approach any movie from ... Casting is so much fun, because I think we all have, or most of us probably have a Rolodex in our mind of film and TV actors that we just really love or we would love to see in X-Y-Z type of role, or we'd love to see them act with some other actors they've never acted with. That type of thing. 

Just purely as a film goer, I'm just excited to see what Jason does in the next, say, 10 years. He's 35 now. I'm curious to see all the roles that he takes on. I fully expect for them to be unpredictable and surprising, and then bold and honest.

That's great. Yeah, me too. I think this is really going to skyrocket him on an even cooler path than what he's one now, so who knows. 

One thing, all of the actors in your films I feel were born for their respective roles. How much involvement are you in when chasing down someone you know really needs to be in the film?

Casting for me is ... There's a saying that ... It's not an original thought of mine and almost a cliché, but I happen to agree with him. Casting actors for films, or rather directing actors for film, 90% of it comes in casting the right person. When I ... Casting is just an entirely creative, it's a deeply creative part of the film making process, and casting directors ... 

The casting director they had at The End of the Tour, her name's Avy Kaufman, and I've worked with her multiple times now. She also casts for Steven Spielberg. She was the one that cast Daniel Day-Lewis as Abraham Lincoln a couple years beforehand. I think she is a real artist, and she doesn't just think in terms of, "Oh, here's an actor that's really great or really cool," in isolation and, "let's talk about the business of getting them into the movie." She really thinks like a painter, and thinks about all of the colors of the canvas and how you would organize an ensemble, and the different dynamic relationships that would occur by putting a different actor next to a different actor. 

A lot of it is ... I'm thinking what I've observed ... with the casting director, [is] a lot of that real sensitivity to performance. It's a real keen awareness of knowing these actors. Casting directors know actors so well. It's not just that they know the movies and TV shows that you and I do, it's that they've been having those people come in and audition for them probably years before they ever became famous, you know what I mean? 

They know every [actor] and probably almost that person probably almost got cast on dozens and dozens of roles that we would never know about. Casting directors know better than anyone what are the very unique skill sets that maybe haven't been explored with these actors and what their quirks are, what they're able to do, what their strengths and weaknesses are.

Anyways, so I get ... I'm in that process right now on the movie I'm doing, and it's really, really gratifying, again. It's like putting actors together who I start as a fan. Who do I think serves the character on the page? Who do I think serves this and will serve the story, and who do I just find riveting to watch? 

For me, when I work with an actor, I always tell them at the beginning that they're my collaborator in the same way that a cinematographer or a composer is my collaborator. They're my collaborator and I'm casting them A, because I think they're appropriate can do something surprising, and honest, and bold with the role, but also I'm casting them for their imagination and for their ability to make choices that are honest but can surprise me and maybe surprise themselves and the person they're working with. I want them to bring all of that, bring everything they have to that role. Yeah, it's so much fun.

I love that answer, because it was just announced that John Boyega [ATTACK THE BLOCK, STAR WARS: EPISODE VII - THE FORCE AWAKENS] is going to be your next film THE CIRCLE, and you've got Emma Watson [Harry Potter Series] and Tom Hanks, and you have the great Matthew Libatique [REQUIEM FOR A DREAM, BLACK SWAN] as the cinematographer. That's amazing. Is there anything that you could discuss about the film that you haven't already, or is it all hush, hush right now?

We're in the middle of ... We're casting the other roles. Some of them are cast but not announced. Some are kind of cast, but the deals haven't been made. Some we're still casting. And right now, and we're scouting. We're shooting all over California, mostly southern California. I'm just excited. Like with anything, I think I bring my own level of neurosis and insecurity to the table, and then I fake it. 

Part of how I'm able to get through it and really ultimately believe in it and make it feel real is by grounding myself with collaborators who really inspire me and people like Matt [Libatique] given me so many great images as a film-goer that are indelible in my mind, told so many stories that I love that collaborating with someone like him or Gerry Sullivan, the production designer who did my last film, but also who did Me and Earl and the Dying Girl and art director with Anderson, or Emma Potter, our costume designer I worked with before. All of these people are just amazing artists, and right now it's that exciting stage where anything's possible. We haven't shot a frame yet, and it's coming together, but it still could change.

Amazing.

It's exciting. Films are exciting. You have a vision, a very clear vision, but it's sort of ... You read about Yoko Ono and her happenings in the 60s, or about great jazz musicians who just put themselves in the presence of other great jazz musicians and tried to be present and tried to react to their environment, to be present and to improvise. 

When you're working with people who are that good, it's just a pleasure. You both want to have a clear, articulated vision of what it is you want, but you also want to let ... It's exciting with the idea that the greatest idea should win out, and you should let it win out, and you're not sure where it will come from, but if you have really brilliant people around you, you're creating an environment where something could come up that surprises all of you. 

That's what you hope for, these happy accidents that I think that are more apt to happen if you prepare it a lot, then at a certain point you kind of let go and give into the collaboration with people who you respect.

Yeah, so every film you make garners more and more in acclaim, which puts you in the spotlight. Do you feel intimidated that each film moving forward needs to be better than the last, or are you just trying to tell a good story, and did I just answer your question?

(Laughs) You sort of answered it. Again, I don't ... I'm sort of in the same way like to for the first first question. Maybe I should be more career minded, but I always just approach things from is this a story that I'm going to be obsessed with for the next two to three years, because that's what it is. It's a relationship from the time that you first ... 

Gosh, from the time I first read Dave Eggers's book, I'm talking about The Circle now, obviously. The time I first read it was September of 2013, and the movie would come out, what, like next year? It's something that I'll be thinking about and talking about and in dialogue with in some ways for years of my life. I just have to believe ... That's a serious relationship. If you're in a relationship with another human being for two or three or four years, that's a significant relationship right there.

I really have to believe that every morning that I wake up I'm going to want to wake up and spend my day with this story and these characters. Then when I go to bed at night, I want to dream of the story and these characters. It has to really feel like a relationship that's one that I really want commit myself to. Then if I can't sincerely say that to myself that I really will, then I'm not the right person to tell that story, and I would be approaching it from maybe a cynical perspective.

As far as the external stuff, like how people respond to what you do, I think everyone ... I think people, if they're really honest, yeah, it's preferable to have people see what you make than not see it. Of course you would probably prefer for people to like it than not like it, but at the end of the day you can't ... Of course I would like those things, but I can't control how anyone feels about anything I make, so I've tried to not obsess over it as much as I used to. 

I'm saying that as though I'm a well-balanced person. I'm probably not. I'm not like a zen person, but that's sort of what I aspire to is to let go of the desire to control things that I absolutely don't have the ability to control or to worry [about], because there's too much to worry about or to focus my energy on, like making a good movie, or loving my wife and son and parents. Those I can control.

Yeah, amazing. Okay, so back to THE END OF THE TOUR. I have hopefully just a few more questions, because I know you're short for time.

Something I'm fascinated with are three moments in the film, and they are when Lipsky invades Wallace's privacy by looking in his medicine cabinet, the hotel room, and his bedroom. I haven't read the book so I'm curious if those were in it or something Lipsky told you about later, giving you purpose of including them. What do you think those moments say about Lipsky's character? Do you think it's part of a mental one-upmanship, indulging in curiosity, or something else entirely?

That's interesting. Some of those details of where he went, what he looked at were things that Lipsky accounted for were recorded. Some of them weren't and felt like they served the truth of the story. Lipsky going into the medicine cabinet, that was in Donald's script, and Donald wrote his script entirely from David Lipsky's book, and then also talking to David. He did not listen to the actual tapes. He just used the book. 

There were many, many, many, many more hours of tapes. I did listen to all the tapes, and I did give them to the actors, but Lipsky going into Wallace's workspace and sort of not turning on the light, that was something that I believe I suggested, and it was sort of a pretty important one for me on a lot of levels. All of it ... There was none of it in the spirit of it of going around and cataloging everything, all of it was definitely in the spirit of things that Lipsky was the first to say that he did.

What's really great, I think, about David Lipsky's book is he doesn't ... he's not boastful or prideful. I don't read that book, David Lipsky's book, and think that it's someone bragging about the time they spent with David Foster Wallace. I read it as someone who is incredibly grateful that they got to spend a few days with a great writer, and in some ways listening to those tapes, which were ... 

When he played those tapes back, they were, what, 12 years old listening back to them with a sense of regret and loss, like a great loss of a great writer, a great man, but also I think a sense of regret of how he spent that time with him. Perhaps he misspent some of that time, that he was chasing certain things, and that in some ways he was probably working from a place of insecurity and chasing a story. He was only 30 years old, and he was probably intimidated, as anyone would have been in that case and just wanting to sound smart and get the right story, so to speak.

I think everyone ... The movie is David Lipsky's story. It's his ... That's the thing that's part of ... One of the reasons I wanted to tell it was it was not a bio-pic. It wasn't purporting to have an omniscient sort of point-of-view or unique insight into what made David Foster Wallace tick in his private moments. It was literally the blind spot David Lipsky. 

What we know is what David Lipsky observed and who David Foster Wallace chose to be in his company, which was as honest or dishonest ... It was him ... I think everyone can have a different interpretation on how much Wallace was performing or being honest or anything. Everyone's been in that situation where we're different people in different situations. If you had a different journalist there with Wallace, it might have been different, an older journalist. If you had a journalist who had a deep history with Wallace, it might have been a different dynamic.

This is Lipsky's experience, and I think there's something very, very relatable and human in David Lipsky's experience of having a little bit of time with someone who he didn't know, and wanting something from him. Wanting something that he probably consciously knew, and then also probably needing things that he was unconscious to him, like probably more internal personal issues of affirmation, professional affirmation and purpose, like an answer. He wanted from someone who probably was saying, "I can't give you what you need." 

But it's interesting. I think everyone has had some experience, some whether they would like to admit it or not, of doing things that Lipsky did. Maybe not in a literal way, but sort of in trying to catalog the stuff of someone's life in some slightly behind-closed-doors way to try to understand that person as though we simply can be understood by the content of our medicine cabinet or our kitchen counter.

I think there's something very human and relatable, something a bit sad about that, especially when someone is gone, because it can feel ... We've all had that experience, right, of having a relationship end, like it could be romantic relationship, and then having to move out or move their stuff out, or someone you love dying and their stuff remaining, and you having to do something with it. That's something we've all had, so I think there's a real level of surrogacy there. After the movie premiered at Sundance, it was something. Some of the journalists that I spoke to said that, in maybe a slightly cringe-inducing way for themselves, acknowledged that I've been there. I've been that guy in those moments, even if I don't want to ... I'm not proud to admit it.

Yeah. Well, sticking with journalism, you have a background in journalism. This movie is about getting a good interview, which I'm trying to do at this very moment. Now that you've made a movie based on the story about getting a good interview, and you have doing some yourself, to you, what defines a good interview?

(Laughs) The interviewers that I really love listening to or reading, someone like, say, Michael Silverblatt, who hosts Bookworm. I did a screening in LA of the movie before it opened, a local NPR sponsored, and Michael Silverblatt participated in the post-screening Q and A, along with [inaudible 00:29:51] Michael. Bookworm has been for the past 25 years ... Maybe I'm probably getting my years off, but may have been the best and definitive show for conversations with authors. Michael Silverblatt was good friends with David Foster Wallace. He had him on the show, I think, five times. Michael said something to the extent of that being a good interviewer involves generosity and being really generous to the people that you're interviewing. I think that's something that ... He articulated it better than I ever could, but I'd certainly ... The documentary that I love - the Maysles brothers [Grey Gardens], Fred Wiseman [Titicut Follies].

I always get the sense that they're able to get access and reveal the humanity of characters by not judging them and letting those people be the best advocates for their position possible, not judging their position, not judging them, but just letting them articulate themselves and reveal their own humanity and allowing them to have dignity, even if you don't agree with what they're saying. You can not agree with it, but you can at least allow them to present themselves without judging them. Yeah, I think curiosity and generosity, and obviously intelligence, and having done the work are ... When someone's clearly coming from a place of really, really doing the work and having familiarized themselves and seeming like they want to know the answer just sounds so base and obvious, but seeming like you want to know the answers to the questions ... I think we've all seen that where it's like someone's being interviewed [inaudible 00:31:27] just checking questions off a list, and they don't really, really want to know. When I sense ...

Man, there's definitely been some really great, like Charlie Rose or Tavis Smiley interviews that I've seen. I think those guys great and entertaining interviewers where it's like if you get to the end of it, it's like, man, they just seem breathless with all the questions they wanted to ask. They probably could have kept going for hours, and they just seem like they desperately needed to know these answers, you know what I mean? It's just like it gives you ... There's a sense of joy you have because you, as a viewer, are finding surrogacy in that person watching them or reading them wish that you could bring that much pleasure and curiosity and joy into all of your interactions. It's not ... John Stewart. John Stewart was amazing, like really, really, really amazing at interviewing people. I believe John Stewart raised the cultural IQ of being [inaudible 00:32:19] or whatever. I think he raised the cultural IQ of America as far as what could be just discourse on a late night show. It was a comedy show, but it was just it raised the IQ points of what could be discussed, what could be taken seriously, even in the context of a comedic show. It's pretty amazing. He clearly was smart. He clearly took the people he was interviewing very seriously, and he brought real A-game questions.

Yeah. I have a million questions to ask, but I know you're limited for time, so maybe I can email you some of them to make it easier for you. I'll go ahead -

Anything you got, send it my way. Honestly, I'm probably ... What is it, 10:10? I'm probably more likely to answer them here, because I go into a black hole once I get off the phone of just like ... it's like work, work, work, put my baby to bed, collapse.

Well, whenever you're like, "All right, man. One more question, because I got to go," let me know.

Okay, I will. I probably have 5, 10 more minutes. Yeah

Okay, cool. Well, okay, so I hope this next question makes sense. How much did you feel like you needed to modulate the meta-ness of conversations David David have in the film, because Wallace kept bringing up the weirdness of the idea of being profiled, which inherently reminds the audience that we're watching the film on a profile of a weekend?

(Laughs) This, it's a great question. It's something we thought and talked about endlessly. I think there's initial impulse if you say we're making a film, and the character is David Foster Wallace, or if it was like [Thomas] Pynchon or someone else where it's like, okay, what kind of post-modern trickery are we going to do in the narrative of the film? That's maybe some immediate question or assumption that I think feels sort of obvious, you know what I mean? You revealed they're not actually having a conversation. It's a recording of a conversation, and it's all in the memory of a baby that hasn't been born yet or something ridiculous. You can have a lot of fun with that, but I felt like it would be disrespectful to what actually happened, and wouldn't dignify what actually did happen, which was ... This was a special encounter, a unique encounter between two guys who did not know each other before, and in the case of David Lipsky, he was deeply impacted by this time.

There's a million other stories one could tell about someone as complicated as David Foster Wallace. Different time periods, you could try to tell all of those time periods, you could tell it through the lens of someone who knew him much better. You could do all these things, but this is what it is, and I think the ... Wallace was someone who was deeply complicated. He was a private person, and yet he was promoting a book that would become a big success. You know what I mean? He became a public figure through his own hard work by writing a great book, by promoting it, by being interviewed by Rolling Stone writers then going on Charlie Rose. He himself ... It's worth noting Wallace was not naïve to the pressures and the requirements of what David Lipsky was doing, because David Foster Wallace himself, I think, wrote the definitive profiles of our life. Whether he's a professional tennis player or politician, he understood acutely what was going on and what the requirements were of publishing something in a magazine.

I think Wallace ... Why I'm interested in this period in time, because this was for Wallace, this was a very good time for him. He'd worked very hard on a complicated book, and the world affirmed it. He was, as far as the things that he'd wrestled with, whether it was issues of addiction or mental health, they were in a good place. He was teaching, and he was a great teacher. This was not a histrionic high or low, like a cliché artistic quote unquote tortured artist high or low. This was him doing the work of promoting the book and him having an opportunity to talk about the themes of the book. They were fresh in his mind, because he was on tour. He was at the end of it. He was at the tail-end of this press tour, so he's maybe just beginning to have some ability to tiniest bit of objectivity, maybe, of being able to reflect on what it had meant to him, both to write the book, and to promote the book, and to have the world like the book.

The book was still very fresh, though. What he was talking about were the themes of the book, which dealt with pleasure and entertainment, the seductive power of image, all of these things, language and image, which were themes of all of his stuff. He was talking about that, but he also didn't want to be a fraud. He wanted to be genuine and genuinely represent himself. He was a complicated guy, and the things that he was talking about I think he just ... There's a really interesting story, a really fantastic story by David Foster Wallace that I would encourage you to read if you haven't called "Good Old Neon", which is in Oblivion, which if you read it, you'll probably ... I think it dovetails perfectly into sort of the question of ... The main character's someone who's profoundly intelligent person who has recognized in their life that they're able to anticipate how other people that they meet might react in every possible scenario - what they might say, what they might do. They've grown, perhaps, bored of people and also they begun to be disgusted with themselves for one, the ability to manipulate other people because they're aware of those things.

I think this encounter between the two Davids, I think David Foster Wallace was ... David Lipsky's a really, really smart guy. I think Wallace, though, was being very honest and candid in what he was saying. He was both trying to answer the questions honestly and also self-reflect out loud on the implications of what he was saying, and the implications of him even doing this interview in the first place, and if this was a necessity of the thing. Wallace had written great profiles before that, and until the end of his life he kept writing articles for magazines, non-fiction articles, and profiling people. He clearly was fascinated by the process, and he loved writing great profiles. He loved great criticism. He was a huge fan of Pauline Kael. He openly talked about Pauline Kael. He was all sides of it - fiction writers, non-fiction writers. He admired ones that were really good, and was fascinated by that process, and it sounded like he had very, very complicated feelings on all of it.

Great. All right, well I have two more questions, then I'm going to get out of your hair.

All right. (Laughs)

Your old professor, who I know you deeply admire, wrote the screenplay, and it's about someone that you also deeply admire. A book-to-film adaptation I feel is hard and scary, and a leap-of-faith project to take on. One reason because certain parts need to be cut for time or continuity. What about Donald's screenplay made you confident that he got the right amount of Lipsky's book in there for a feature?

It's interesting. David Lipsky's book came out in 2010. I read it quite early on, and the book was widely read. David Lipsky had written an article, and it's worth noting David Lipsky was an acclaimed journalist. These guys hung out in '96. In 2000 David Lipsky had a book come out called Absolutely American, a non-fiction about his time that he spent at West Point, which is a Time Magazine Book of the Year. David Lipsky was publishing all the time in Rolling Stone. I interned at Rolling Stone actually around 2000. I never knew David Lipsky, but I was aware of his name. It was a huge name, and is in that regard. When Wallace passed away, Lipsky wrote an article in 2008 for Rolling Stone, whose title I'm going to mangle, it's worth checking out, but it's something to the extent of, I am paraphrasing, "The Lost Years and Last Days of David Foster Wallace". Something like that, and it won a national magazine award.

After he wrote that, it was Wallace's that kind of urged him to do something with these tapes and write this book. Lipsky's talked about this a lot. When Lipsky's book came out, it was a New York Time's Best-seller, an acclaimed book. It wasn't an obscure book. It was everywhere, and I read it. A lot of people knew who were Wallace fans read it, and I was really moved by it. I thought it was a beautiful book. I loved hearing Wallace's voice. I loved hearing ... It wasn't simply transcriptions. It would be really reductive and disrespectful, I think, to the work, the real work that David Lipsky did that just refer to his transcriptions. There's something really creative and artistic he did, and it's fused with emotion, and empathy, and admiration, and intelligence. That all being said, I didn't read it looking at it as could this be a movie? I didn't think about it in those terms at all. I just read it, because I'm a Wallace fan and was very, very ... I found it insanely funny, because Wallace was super, super funny, as was Lipsky, and they were talking about so many things.

They were talking about pop culture half the time, things that I had thought about at ... At the time they spent together I was, I think, what, a junior in high school. So all the stuff that was on corporate radio or things that I was completely aware of and thinking of at that time, so it was just hearing these guys, two guys who seemed to respect each other's intellect kind of jousting about all these things. It was just a real pleasure. It made Wallace feel alive, and the fact that he was not, there was this sense of grief and loss. There was emotion in it. That's what I remembered. Surprising emotion.

When Donald reached out, told me he adapted it, I sort of was like, "Oh, that makes sense." I could see ... I was like if anyone could crack that or could turn it into something maybe amazing, it would be Donald. When I think of his plays, the ones I really love, whether it's Dinner with Friends, which is one he won the Pulitzer for, Sight Unseen, or Brooklyn Boy, many of those plays deal with the lives of artists. It's just a world that Donald's been writing about for decades. The lives of artists, he knows it, and they're human, and subtle, and intelligent plays. When I did read it, I read it with a level of excitement and fear. It really was great in that it didn't ... It was respectful to actually what had occurred, which was two guys who were stranger spent a few days together and talked about like, talked about literature, talked about culture, talked about meaning, purpose, all these things, and then they say goodbye and never talked again.

That's what happened, and that's what Donald's script was, but in it he found real meaning and real emotion, and I think was very, very respectful and avoided all of the cliches that I think we've just come to expect from the traditional biopic and portraits of artists that we've seen and we can rattle of a list of. Then he types the end on the typewriter and rips the page off, and says, "By God, I've done it," or he crumbles up the paper, and we pan around to reveal a massive mountain of crumbled up paper, or splattering paint, throwing the painting out the window. All these cliches we've seen them, we know them. He avoided all of them, and it was like, "Oh, yeah. Of course." It just packed a real lollop that, for me when I read it, there were just so many things about these two guys.

At the time that they spent that time together, Wallace was 34, Lipsky was 30. I think I was 34 when I read that script. It was just I related deeply to everything these guys were dealing with and talking about. I related probably mostly to Lipsky, because I spent far more just casually in the company of someone who I admire but is not my friend. I know what that's like, and I think we all know that that's far more relatable than really, really going deep into a portrait of what's require to write a thousand page novel and tortured, complicated genius, et cetera, et cetera.

Yeah, so when I read it, it immediately reminded me of my favorite sort of platonic love story, relationship story, road films, the Wim Wenders films, the road films of the '70s, like American Friend, movies like California Split, the D. A. Pennebaker documentary. Don't Look Back was something that I immediately thought of that really struck a chord with me. Movies like the Midnight Cowboy, movies like Amadeus, movies that dealt with ... Movies like Master and Commander, movies that were surprising stories about relationships, and friendship, and competition, and intelligence, and self-worth, and meaning. They were all these things, and Donald, he didn't write a play. He wrote something that really the main character was the American mid-west. It was the mid-west and being aware of how it exists between coasts.

This book ended by David Lipsky in New York who was and is a New Yorker, and Wallace was someone who spent the majority of his life in Illinois. Not all of it, but most of it. I was excited to have that be a character, because the places that become the backdrop of the story that are the characters in the story - late night diners, multiplexes, big malls, 7-11s - those are things that, to me, are not kitsch. There's deep emotion and nostalgia, and comfort in those places, because I'm from a ... Where Wallace grew up was a college town. He taught at a college in a college town which was surrounded by a pretty rural area. That's exactly how I grew up in Athens, Georgia. There's just ... Yeah.

Awesome.

I read it, and I saw the movie in my head. I rented the VHS for the first time when I was 18 years old, a year after it came out in 1997. I read it again in my late 20s. I read it again before I made the film. It hit me in the gut in different ways. Different characters I connected with at different points of my life. When I read it in my teens, 20s, or 30s, in so many was I just felt like that the film when I saw in my head when I read Donald's script, if I could get it right I think it would be really meaningful for the issues that it wrestles with and that these characters wrestle with. Beyond myself, I couldn't really predict how other people would respond, but I knew it was something that I absolutely could stay in love with for several years or the several years that it took to make it.

Yeah. That's great, and I'm glad that you talked about the meetings, because that kind of is my final question. After seeing the film, I tweeted that the movie is an effective and potent observation of the fear of loneliness. Would you agree with that, or do you think there's more to it?

That's a totally spot-on observation but I think there's more to it. It's funny. David Foster Wallace was, in addition to being so many things, he was I think one of the funniest writers of his generation. I think people usually it's more obvious in his essays, but Infinite Jest is a profoundly funny novel, amongst other things, amongst being heartbreaking, imaginative, and all these things. When Wallace would talk about it, he would say he wanted to write a book about sadness. That was the word that he would use when describing Infinite Jest. It was about sadness, then obviously all the other things it was about.

Yeah, listen. We've all had that experience of desperately wanting something, a person, a thing, a career, whatever it is, and then meeting someone who has that thing or those things that we want that we covet, but they have them. They're the definition of those things in many ways. Then in some moment of unique insight or epiphany, they reveal, either intentionally or unintentionally to us that that thing alone that you desire is not going to fulfill you. It's not going to make the depression go away. It's not going to make the loneliness go away. It's not going to make the sadness go away. It's not going to give you all of the purpose and definition that you seek, that you will still be yourself. Then you have to figure out what you're going to do tomorrow. 

We've all had that, and I think that was sort of the experience that Lipsky had was I think he craved, like any young writer ... Lipsky was already an acclaimed writer, it's worth noting. One way this is very different than Almost Famous, he wasn't a teenager. Lipsky was 30. He already had a collection of short stories and a novel come out that were very well reviewed, and he was writing for Rolling Stone. He already had that success, but the success that Infinite Jest received, the acclaim it received was very unique for any novel at any time. It felt like, probably, David Foster Wallace was the absolute center of the literary universe. I think Lipsky wanted to know, like I'm sure lots of writers want to know what does it feel like to have done that and to have ... Can you tell me? It's a very hard thing to articulate to someone what that's like.

I think also it's you feel false ... I'm sure Wallace would have felt falsely modest to say at the end of it it didn't effect him in the way he thought it would. Probably effected him in different ways. When people so clearly want something you have in that regard, no one wants to be the person to say, "Pursue other things if you're looking for meaning and happiness." No one wants to say that, because you sound like a jerk, and Wallace was not. I think he was very compassionate, and thoughtful, and generous with Lipsky.

Awesome. Man, thanks so much for taking the time out of shooting - 

Of course, man.

- shooting to chat with me. Good luck on THE CIRLCE, and I look forward to seeing it when it releases. Hopefully maybe we can do an interview before it releases.

I would love that, man.

Yeah, that would be great. Well, yeah. Thanks again, man, and good luck with everything. You're doing wonderful.

Thank you. Thank you for all of your beautiful, thoughtful, intelligent writing over the years. Really, really means a lot to me as a reader, so thank you.

Thanks man. All right, man. Have a nice day and a nice weekend.

All right, you too. Take care. Bye.

Bye, bye.