Seldom has an author become so entangled with the romance and mythology of their work as Jack Kerouac. But the cult of personality that rose up around him was something the author loathed, so it’s somewhat ironic that the myths surrounding him continue to this day, nearly a half century after his death in 1969. 

At the time, a zillion footloose youth around the globe were trying to live out their own On the Road, which was published a dozen years earlier and had become one of the hippie movement’s sacred literary texts. Few of them had any idea that it was in fact its author’s most compromised book, the only one that was edited from his stream-of-consciousness final draft into a more marketable and conventional narrative and stylistic shape.

And those readers mostly ignored or refused the fact that On the Road’s thinly-veiled protagonist “Sal Paradise” was now a terminal alcoholic living as a recluse in Florida, angrily decrying the counterculture his books had done a great deal to foster.

But that sad, embittered figure is not the Kerouac of pop myth: the handsome, hopped-up, jive-speaking, and possibly bisexual adventurer of twenty years earlier, when he was just meeting fellow leaders in what would be called the “Beat Generation” — another label he’d come to hate.

Instead, it’s a more romanticized image of the author that dominates most films about Kerouac, which have come out more and more frequently in recent years. Yet films actually based on his prose-dense, plot-thin novels are few; more have deployed Jack Kerouac himself as a character in dramas that vary between fact and fiction.

One that seems to hit all the marks is Michael Polish’s Big Sur (2013), based on Kerouac’s 1962 roman à clef — but with the names switched back from their fictive guises to the real people he was writing about. Thus the novel’s “Jack Duluoz” is now duly Kerouac (Jean-Marc Barr), “bored and jaded” three years after the publication of On the Road, or, as he describes: “the book that made me so famous I’ve almost been driven mad.” He cautiously emerges from hiding to accept poet Lawrence Ferlinghetti’s (Anthony Edwards) offer of a cabin in the titular coastal area as a place to get his creative juices going again. 

But already well in the grip of the bottle, Jack finds it hard to resist partying in San Francisco, or reuniting with such “bad influences” as Neal Cassady (Josh Lucas). When he steals the married latter’s lover Billie (Kate Bosworth), he’s soon driven into a panic by her demands, emotional and otherwise. She becomes just another facet of the “public” that is endlessly requiring little pieces of his soul, and which he escapes through boozy self-destruction. Beautifully shot by M. David Mullen (The Love Witch, Twin Falls Idaho), Big Sur is rare as both a relatively faithful adaptation of Kerouac’s writing, and as a dramatized portrait of his real-life decline. 

The only big-screen adaptation of his work that Kerouac actually lived to see must have horrified him, though the $15,000 he was paid for screen rights did enable him to buy a house on Long Island. The MGM flop, The Subterraneans (1960), turned his novel about a stormy interracial romance into a ridiculous caricature of “Beat” stereotypes, with the book’s African-American love interest magically transformed into the very white, very French, Leslie Caron. Others in the orbit of George Peppard’s aspiring-writer hero were such dubious hipsters as Planet of the Apes’ Roddy McDowall and future Laugh-In comic Arte Johnson. Under the direction of one Randall McDougall (who started his directing career with Joan Crawford and ended it with something called The Cockeyed Cowboys of Calico County), these figures flit through stagey coffee houses rife with bongos and interpretive dancing. Even curious spectators in hicksville cinemas knew they’d been had.

Nonetheless, Kerouac hoped On the Road would be filmed, if only for the financial windfall. After its publication attracted enormous attention, he dreamed of a movie starring Marlon Brando as “Dean Moriarty” aka Neal Cassady. But that actor wasn’t interested. Over the ensuing decades, many filmmakers were — including Francis Ford Coppola, Joel Schumacher, and Gus Van Sant. When Brazilian director Walter Salles (Central Station, The Motorcycle Diaries) and playwright-adaptor José Rivera finally got the green light, they surrounded relatively unknown leads Sam Riley and Garrett Hedlund with a starry supporting cast, including Kristen Stewart, Viggo Mortensen, Amy Adams, Kirsten Dunst, and Elisabeth Moss

Once the movie finally premiered at Cannes in 2012, few doubted the good intentions and intelligence of its collaborators, but in the end, their On the Road only proved what had been obvious to others for fifty-five years: This digressive, hypnotic, impressionistic book is not natural screen material.

Though he was dragged kicking and screaming into the occasional television interview, Kerouac made almost no movie appearances himself. The sole exceptions were his role as narrator (and scenarist) on friend Robert Frank’s half-hour 1959 goof Pull My Daisy, an experimental frolic for “beat” luminaries including Allen Ginsberg and Gregory Corso. He also briefly showed up in one of Andy Warhol’s earlier stationary-camera exercises, 1964’s Couch, again in the company of his aforementioned fellow travelers.

However, he has been portrayed by actors in many films: fleetingly in 2000’s Beat (with the gruesome twosome of Kiefer Sutherland and Courtney Love starring as Mr. and Mrs. William S. Burroughs), as well as in Howl (2010) and Kill Your Darlings (2013), which starred Daniel Radcliffe as a very young Allen Ginsberg. There was also the little-seen 2007 biopic Neal Cassady, and the underrated, Cassady-focused The Last Time I Committed Suicide (1997), in which Kerouac is played by none other than Keanu Reeves — and not badly, either. Until Big Sur, probably the most substantial dramatic portrait of the author was in 1980’s Heart Beat, which charted the long, complicated relationships between Jack (John Heard), Neal (Nick Nolte), and Carolyn Cassady (Sissy Spacek). It’s one of those films that has so many right ideas, you can’t quite figure out why the whole thing feels so wrong. 

For the real deal, of course, you can always watch any of the innumerable documentaries about Kerouac and the Beats in general. Any list — even a partial one — needs to include: Kerouac (1985), What Happened to Kerouac? (1985), Burroughs (1983), The Source (1999), Destroy All Rational Thought (1998), Ferlinghetti: A Rebirth of Wonder (2009), and The Beat Hotel (2012).

Besides Salles’ sincere but flawed adaptation of On the Road, one other iteration that might be found is Route 66, which ran for five seasons from 1960 to 1965, and starred George Maharis and Martin Milner as two hip (but clean-cut) young “drifters” in pursuit of adventure and romance on America’s highways ’n’ byways. It was widely considered a sanitized rip-off of the Kerouac’s recently famous book, and indeed the author himself strongly considered suing the show’s creators and its network, NBC.

Our near-mythic scribe had the last laugh, however: Though hugely popular in its day, Route 66 is largely forgotten now, while On the Road and Kerouac remain forever famous. Whether he’d like it or not.

Watch Now: Michael Polish’s adaptation of Jack Kerouac’s Big Sur. And don’t miss the Kerouac-adjacent documentaries, Ferlinghetti: A Rebirth of Wonder, Destroy All Rational Thought, and The Beat Hotel.

Here at Fandor we love movies, but that doesn’t mean we don’t also like to curl up with a good book! Keep celebrating National Author’s Day with us by reading “What Makes a Book Impossible to Adapt?” and watching our video essays, “What Does a Book Say About a Character?” and “Whodunit? By the Book.”