Happiness is as elusive for David Foster Wallace (Jason Segel) as literary success for David Lipski (Jesse Eisenberg). And while countless of films would take that scenario and have their characters discover some measure of joy at the end, this is smart cinema. It is also based on real life, which lowers the happy ending probability by more than half.
I call this smart cinema not because it is mainly constructed of one conversation after another; compelling drama is not defined as two people in a room sharing a dialogue. Take for instance one of the first conversations the Davids share, in which Foster Wallace predicts the omnipresence of the internet a decade from where he sits, and mentions the allure of masturbation without the demands of compromise. Spoken by any other character, the words would seem pretentious; here, they not only ring true, but near depressing.
And that is a feeling that never completely vanishes. It is there as the two men eat junk food in a car; it is there as they converse with women; it is there as David hesitates to hug David, and ends up settling for a friendly handshake. The only scene in which I would argue there is hope is the very last, in which a clumsy David Foster Wallace dances about in a church, surrounded by stranger. And this moment is the most powerful in the film particularly because of hope. For the briefest of seconds, David Foster Wallace is free. And it aches, because he could not remain that way.