The film opens in 2008. David Lipsky (Jesse Eisenberg) is working at home on his laptop when he gets a call from Bob Levin (Ron Livingston). Levin tells Lipsky that he has gotten an unconfirmed report that writer David Foster Wallace (Jason Segel) has committed suicide. Lipsky refuses to believe it, thinking it is kids causing a death hoax. He searches for the news online, which only confirms what Levin told him. Lipsky is shocked to the core. As news of Wallaces death spreads, numerous people write tributes for him. Lipsky reads a eulogy at his local radio station.At home, Lipsky searches for some old cassette tapes and batteries to play the recorder. As it powers up, he hears Davids voice as if he was still alive. Lipsky drops the tape recorder to the floor in shock as he listens to the man he once interviewed for five days.12 YEARS EARLIERLipsky is doing a public reading of his novel, which has been a moderate critical success. Afterwards he goes to a bar to meet up with some friends. One woman mentions this amazing author that she just found out about named David Foster Wallace. Lipsky is intrigued.Back at his apartment, Lipsky reads a glowing review about Davids work to his girlfriend Sarah (Anna Chlumsky). The reviewer is basically saying that the best of the year has already been decided and Davids novel Infinite Jest is nothing short of genius. Sarah jokes that if the book is so great perhaps he will have to read it. So, Lipksy buys a copy and begins to read it. Shit, he says halfway through, in awe of the mans talent.At the offices of Rolling Stone where he works, Lipsky goes to his boss Bob Levin and tells him that Rolling Stone has never interviewed a writer but they should interview David Foster Wallace because he is the leagues of such greats as Hemingway. Lipsky promises Levin there is a story there. After mulling his decision, Levin goes to Lipsky and grants his request, telling him there better be a story there.Lipsky packs his bag for the trip while Sarah watches, starting to read Infinite Jest herself. He grabs a copy of his own book off the shelf, apparently as a gift for David. Sarah smiles at the act while Lipsky just shrugs.DAY ONELipsky gets on a plane to Illinois, and rents a car. He gets lost, and calls David from a payphone to ask for directions to his house. David asks where he got his number. Lipsky says his publicist gave it to him in case of emergency. Youd do me a favor by losing it, David says abruptly. Lipsky is stunned by his bluntness.Lipsky finally arrives at Davids house where David is waiting for him, along with his two large dogs. They awkwardly say hello and go inside. Lipsky compliments on the house and its view and begins to get ready to start asking questions. Lipsky apologizes about calling David but David brushes it off. The reason he was curt with Lipsky (though noting he was mostly joking with him) was because he had to unlist his number due to fan calls, and people contacting his parents to find him.Lipsky is using a tape recorder to catch everything they talk about. David however, has a request before they truly begin; that they have strict off the record guidelines. If he is to say something he does not want recorded, Lipsky is not to use it later for the article. Lipsky gives him his word that he will stop recording whenever David wants him not to talk about a certain subject.David and Lipsky drive to the college where David teaches. David says he feels bad since the book tour caused him to miss several weeks of classes. Lipsky sits in on a class and sees how easygoing yet critical David can be when he is trying to teach to his students. Lipsky tells David after that it is clear that his students love him.David and Lipsky go eat at a diner. David orders a soda so Lipsky does the same. Lipsky is cautious in his first questions, asking David about drinking, but David assures him it is not a problem, and Lipsky can drink in front of him if he wishes. Lipsky admits he was unsure and ordered a soda too to be respectful of David. David asks Lipsky on how he sees this interview. Lipsky says it will be about how it is like to be the most talked about author in America today.David begins to talk about the tour and how he admits that he hoped that he could get laid a few times because of it, though he admits how awful that sounds. He also notes he wouldn't be able to straight up ask a woman to go with him; he would need them to basically tell him they were going to the hotel with him. David then says hes glad it never really happened because it would make him feel lonely. When Lipsky asks why, David says it is because he would know it wouldn't be about him, it would be about his fame.Lipsky then comments that people might thinking by reading his personal books might be a way in their eyes to know David himself. David says that it is a really good quote. David tells Lipsky he is afraid of being a whore; using the tour, this newfound fame for bad purposes, for cashing in on his art.David and Lipsky go to a convenience store to buy soda and a bunch of junk food. When Lipsky tells David that he has an expense account with Rolling Stone that will cover everything, David gets more.In the car, they talk about the awful nutrition of candy and sweets but how tasty it is and how good it makes you feel. They discuss pop culture and how it is usual bad quality, which segues into a short discussion about how good the first Die Hard is.David and Lipsky return to his house. David talks more about Infinite Jest. He says the book is asking the question why? Why do people do what they do if it makes them unhappy?Inside, they discuss meaningless acts such as watching too much television or compulsive masturbation. David then goes on a long monologue about the future of pornography and how it will desensitize an entire generation into accepting a soulless stimuli for primal release because it is easier to be alone with an illusion that to be real with a person.Lipsky, a smoker like David, asks to try some of his chewing tobacco. He immediately cant stand it and asks to use the bathroom. He spits it in the sink then looks into Davids medicine cabinet, looking for clues.Leaving the bathroom, Lipsky returns to the living room, noticing David has no TV. David says that is true, because if he did he would watch it all the time.Lipsky asks if David is currently dating anyone. David says no, noting he is completely out of practice and wouldn't know how to do it anymore. He has wished since being on the book tour that he was married since he would be able to share it with someone that didn't have an agenda and would listen to him. His friends, editors, and Lipsky himself may like him and care about him, but they all have an angle to play.David asks why Lipsky isn't married at 30. Lipsky says he is not sure how he can find a person that can fit with him especially they would be with him for the next thirty to forty years. David says he isn't at 34 because he knows that he is hard to be around. His particularly way of living needs him to be alone when working for one, and this could lead him to become quite selfish with how he acts.Changing the subject, Lipsky asks about an Alanis Morissette poster David has. David says he is a fan and he likes her because she is a pretty girl that doesn't seem fake; someone you could actually meet in real life. David admits he has a crush on her and would like to meet her, but would be too flustered to manage a conversation. David doesn't want it to look like he is using Rolling Stone to get her attention. Lipsky dryly notes that Rolling Stone has been used for worse.David notes that it is late and they need to be up early to catch a plane for the last book tour stop. Lipsky goes to get a motel room but David offers him a guest room instead. Lipsky cant sleep and looks around the room, where David has numerous copies of his books laying around.DAY 2Lipsky wakes up and goes into the kitchen where David offers him coffee. Lipsky declines, and gets a cigarette to smoke instead. David offers him half a pop tart but Lipsky declines. David gives him half and insists. "Mi pop tart es su pop tart", David says.David and Lipsky drive to the airport. Lipsky asks why he doesn't live in New York. David says he can't deal with the ego of the people there. Lipsky then asks about his trademark bandana. David cant believe that is a real question. He finally admits that he started wearing them in Arizona when it was really hot to keep the sweat off his typewriter. He then became comfortable with them and knows he uses them as a bit of a security blanket. He hates the idea that they have become a trademark of him.David tells Lipsky that he started writing seriously around age 21 and he didn't have much inclination to write before though he wrote a terrible WWII novel at age 9.Lipsky asks about Davids parents and wants to ask some questions about his youth. David tells immediately that his parents are private people and he would be not comfortable with that, and tells Lipsky no, he is not allowed to. Lipsky says okay.As they wait for the plane to take off, Lipsky asks David about the worst job he ever had. David mentions being a security guard and a towel boy. Lipsky then mentions he knows about Davids eight day stay in a mental hospital, which makes David shut down. Davids voice gets a bit cold and he explains he checked in himself because he Didnt want to do something stupid. He explains he had a friend in high school that attempted suicide and failed and only resulted in giving him brain damage.David says that he was depressed. He had a good 5 year run and things werent going his way anymore. I thought my life was over at 28, David says. Lipsky notes that he turned it around though and is now promoting a critically acclaimed and bestselling novel. David is silent for a moment then looks at Lipsky."Dave, this is nice. This is not real," David says.They make it to Minneapolis where they are met by an overeager escort/driver for their trip Patty (Joan Cusack). Patty drives them to the hotel and they check in.In his room, Lipsky checks in with Levin, who asks him if he asks David about the heroin rumors. Lipsky says he hasnt gotten to it yet, and David is hard to open up. Levin asks if he likes David, and Lipsky admits he does. Youre not his friend, youre a reporter, Levin barks and tells him to get the story.That night, David and Lipsky attend the final reading at a bookstore where a full audience is waiting. There Lipsky meets David's friends Julie (Mamie Gummer) and Betsy (Mickey Summer). Lipsky learns Julie writes poetry and got one published, and tells her he wrote a book himself. Before David gets on stage to do a reading, he requests from the store owner that he not do a Q&A. "It's not because he is unwilling to do one per se, its just that the questions are quite repetitive, such as Where do you get your ideas?"David goes out on to the stage to rapturous applause. Afterwards he signs books for fans.David, Lipsky, Julie, and Betsy go for food after at a diner. David explains he uses his entire name because his name was common and there were a few David Wallace's already.The four drive back to the hotel, belting out Alanis Morrisette, with David staying silent.Back at the hotel, Lipsky and David discuss audience love. David is afraid that the wrong kind of audience will love him. Lipsky confesses that Sarah loves Davids work and he is afraid she loves his writing better than his own. David asks for him to get her on the phone. Lipsky calls her and David speaks to her for 25 minutes, thanking her for liking his work. Lipsky later explodes on his girlfriend for talking to him that long, jealous.DAY 3Lipsky goes to David's room, surprised he is not ready. He knocks on the door and David peeks out. David said he got caught up in a TV marathon and he is almost ready. Lipsky waits for him in the room, sensing something is off about David.They get out to the car where Patty is waiting for them. Patty comments on Davids clothes, which is what he usually wears anyway."You're wearing that? Patty asks."For a radio interview, yeah", David replies, confused.David and Lipsky go to a radio station and David gives a great interview. When they get out, Patty is ecstatic, saying David did so good and awkwardly says she will have to buy his book now for sure. Patty says they have the day so they can go anywhere they want. David asks if she knows where The Mall of America is and Patty says she does.David and Lipsky sit and watch the amusement park rides in the mall. Lipsky asks who David thinks his audience is. David says a young man in their 20s who have problems with loneliness. David says most people under 45 have feelings of loneliness a lot because they have done all the things that society expects of them to be happy, yet they are not content with the life they have.David also explains the quandary of selling a lot of copies. Mainly, things that sell a lot are usually bad, but if you happen to sell a lot of copies, then your argument/defense mechanism (of saying people have no taste/that you cannot believe your work cant sell) falls apart.Julie and Betsy meet the two and they go to see the movie Broken Arrow. Afterwards, David asks if they have a TV so they can watch some.Lipsky talks to Julie at her home, and asks he can follow up with her about David in grad school. Julie says it is okay, as long as David says it is okay and gives him her email address. David sees this and becomes enraged with Lipsky, thinking he is flirting with Julie. Lipsky denies it, and says he only got her email address. David then says he doesn't want him to talk to Julie. He says he told Lipsky him and Julie dated in grad school and he shouldn't be flirting with a woman when he can't figure out what he wants anyway with his girlfriend."Just stay away from her, okay?" David asks being a combination of angry and sad. "Be a good guy."Lipsky, angry at David, breaks his no drinking rule and gets a beer and watches David watch a movie.On the taxi back to the hotel, Lipsky offers to pay with his expense account, but David firmly tells him he will pay.They get into the elevator in silence. On the way to their rooms, Lipsky tries to apologize but David ignores him.DAY 4Lipsky and David get on a plane back to Illinois. They are in separate seats this time. Lipsky looks back at David. When they return, Lipsky is searching for the car in the parking lot but it takes him several minutes to find it to Davids frustration. David asks why he didn't write down where he parked and Lipsky says he doesn't know, further noting that he's a "fuck up". David asks what his problem is, and Lipsky shoots back what is his. They get in the car and drive off.In the car, they trade shots back at each other. Lipsky thinks Davids problem is that You still think youre smarter than other people. David says "I don't believe writers are smarter and does not meaning people are not better in other areas than him." David notes that he treasures his regular guyness but Lipsky believes that is a cop out."You don't crack open a thousand page book because you hear the author is a regular guy. You do it because hes brilliant," Lipsky says.David basically shuts down at this point, saying he can no longer give Lipsky what he wants without seeming fake.Later, as David drives, he notes he is feeling the end of the tour, and that he had to shut down emotionally during the time and now he has to feel it all. He notes he doesn't like the attention and if he became a sellout he would rather be dead. He says tomorrow, Lipsky will go back to New York, and he will go back to knowing 20 people. "The tour is like heroin to the cortex", David says. Lipsky perks up, having the in to ask the question he has meaning to since the interview began.When they get back inside the house, David tends to his dogs while Lipsky turns his tape recorder back on. Lipsky finally asks about the rumor of Wallace using heroin which pushes David to his breaking point."I was not, I never was involved with heroin", David says. He knows Lipsky wants something to make the article seem sexier and drugs are sexy to readers, despite David telling him television was the biggest addiction of his life. David talks about his depression and how he drank a lot and it was a clinical numbing so he could try and function. He mentions the room he stayed in during his hospital stay and how he had to be watched constantly in case he hurt himself.Lipsky goes to bed, realizing he may have gone too far in asking David those questions. David comes into his room and talks to him more, calmed down. He tells Lipsky that his depression wasn't due to brain chemicals or alcohol. It was because David was unhappy at being ordinary, of doing everything expected of him, and feeling no contentment. "All your actions are false, and it means nothing. It's an illusion and it makes you feel horrible. I don't think people change. I still have those parts in me. I just don't want them to take over and drive, David says.David leaves, and Lipsky quickly writes down everything David said.DAY 5Lipsky wakes up and sees David. David looks happy and chipper compared to last nights talk.David and Lipsky go on a walk in the snowy grounds around his home with his dogs. They both comment on how beautiful it is. Lipsky asks to take David somewhere nice to eat before he leaves. David decides on McDonalds.Back at David's house, they eat their food. David gets a call and tells the person he would like to go, but he has someone over right now. Lipsky asks what the call about. David says it was about a dance he goes to at a local Baptist church, since he found he likes dancing. Lipsky ponders the location and David shrugs. Baptists can dance, he says. Plus, this type of dance is more of a solo affair which allows him the solitude he craves while still being around people. David says before Lipsky leaves they should exchange addresses. Lipsky agrees.Back in 2008, Lipsky continues to listen to the tapes, tears in his eyes.While David is outside the house, Lipsky goes around the house and using his tape recorder, speaks about everything he can see, in order to better articulate it in his writing.Outside, Lipsky hands a copy of his novel with his address information inside the jacket. Lipsky thinks what he is doing is silly, but David thanks him and says he looks forward to reading it after he finishes his next book. David promises to tell him what he thought when hes done. Lipsky tells him not to worry too much since it didnt sell well.Before he gets into his car, Lipsky asks one last question. "Is it reassuring that a lot of people read you?" Lipsky asks.David responds that it causes people, including yourself to have unrealistic expectations. The more people think you are great, the bigger the fear is of being a fraud, David says. Before Lipsky leaves, David tells him, "I'm not so sure you wanna be me.""I dont?" Lipsky replies.David tells him to give his regards to his editor. Lipsky drives back to the airport.Back at home, Lipsky begins to write his article on David. He gets a package from David, containing a shoe he accidentally left behind and a short note, nothing else. Lipsky is left bewildered and confused.Though not stated in the film, the article is never published in Rolling Stone.Several years after David's death, Lipsky uses the tape transcripts to write a memoir about his time with David, which becomes a bestseller. While we see David dance at a Baptist Church, Lipsky reads his memoir to an audience. He remembers the time he spent with David driving around and that those talks were the best of his life. Lipsky says David thought books allowed people to feel less alone. Lipsky says that he wished he could have told David, that being with him, during those five days, made him feel less alone.