When the adaptation of Jack Kerouac’s On the Road hits theaters on May 23, it will leave a long, storied history behind it. Back in 1957, Kerouac famously wrote Marlon Brando a letter attempting to convince the dude to star as Dean Moriarty (with Jack himself taking on Sal Paradise). Appropriately, Kerouac had a plan: “Don't worry about the structure, I know to compress and re-arrange the plot a bit to give a perfectly acceptable movie-type structure: making it into one all-inclusive trip instead of the several voyages coast-to-coast in the book.” Also: “I wanted you to play the part because Dean (as you know) is no dopey hotrodder but a real intelligent (in fact Jesuit) Irishman.” And: “What I wanta do is re-do the theater and the cinema in America, give it a spontaneous dash, remove pre-conceptions of 'Situation' and let people rave on as they do in real life. That's what the play is: no plot in particular, no 'meaning in particular, just the way people are.'” The project never came to fruition, and Kerouac never got to "re-do cinema in America." Fast-forward a few decades, to the early nineties, and On the Road was on the boards again, this time with Francis Ford Coppola directing and Brad Pitt and Ethan Hawke starring. And then that fizzled too.
A bevy of other iterations have existed (before and after Pitt/Hawke) until this final team was locked in: Walter Salles, the Brazilian director behind The Motorcycle Diaries, making a return to English-language filmmaking; Garrett Hedlund, the Tron: Legacy cutie, as Dean; and Sam Riley, a young Brit, as Sal. (Also in this movie: Kristen Stewart, technically topless! Ahhhhh!!!) So can these smaller names pull off the big book? It’s not an easy task. On the Road’s a classic, to be sure — I mean, come on: It inspired Katy Perry’s “Firework” — but it’s the kind of classic often given as a high school graduation gift. In the wrong hands, this could all come off a touch corny. Like, “the only people that interest me are the mad ones ... the ones that never yawn or say a commonplace thing, but burn, burn, burn like roman candles across the night”? How are you going to figure out how to, say, adjust the GPS, or figure out where to illegally stream Revenge, if you only have friends that never say commonplace things?