At its heart, the film is about the friendship between Wallace and Lipsky. An aspiring novelist himself, Lipsky's intimidated by Infinite Jest and all the critical praise heaped upon it. His writing seemed conventional by comparison, a fact made all the more annoying when his girlfriend cannot stop praising Wallace. Meanwhile, Wallace envies Lipsky's ability to charm his ex-girlfriend. Meanwhile Rolling Stone pressured Lipsky to prod Wallace on his struggle with addiction, creating a dramatic tension throughout.
Snarky reviewers have compared the Wallace/Lipsky relationship to Mozart and Saliari in Amadeus, the genius toying with the mediocrity. I would disagree, the proper analogy would be James Boswell and Samuel Johnson, for when the biographer illuminates their subject they provide a great gift to future generations.
I watched the film in a packed theater. While the audience laughed at the banter on Alanis Morissette and junk food, I sensed an uneasiness when Wallace pontificated on the dangers of technology. His words do seem prophetic as you can sense people itching to check their phones as the movie's playing. Their looks seemed to say, How could this brilliant guy with the brightest future before him feel so unhappy and lonely? I'll credit Segel's performance for refusing to turn Wallace into a tortured artist cliche, provoking the conflicted reaction from the audience I sensed in the theater.
In addition to his fiction, Wallace shined in his non-fiction writing, most famously "A Supposedly Fun Thing, I'll Never Do Again," an uproarious chronicle of his week on a luxury cruise ship. His journalism is a great place to start.
As a drama, The End of the Tour hits all the right notes: the bleak beauty of winter in the Midwest, the cold comfort of chain restaurants, and the millennial unease of the 90s. When they share an awkward goodbye at the end (should we hug or shake hands?) we feel a sense of loss as Lipsky drives away. The ending echoes My Dinner With Andre because we're sad to leave our friend, especially when you know they're never coming back.