Hollywood doesn’t come out with many literary comedies anymore, or films that center around the extracurricular adventures of middle-aged professors, but it did both back in February of 2000, twenty years ago, with Wonder Boys.

VILLARD BOOKS

Based on a novel of the same name by Michael Chabon, Wonder Boys tells the story of Grady Tripp (Michael Douglas), a writing professor at a liberal arts college somewhere in Pittsburgh, a man who had a massively successful first novel years earlier, but has been struggling ever since with the follow-up. Also, he might be looking at impending fatherhood.

The film boasts one of Michael Douglas’ better late-period performances…

As the film begins, Grady has just been left by his latest wife, but is carrying on an affair with the married president of the university (Frances McDormand). The plot is set over the course of a single weekend as the college hosts a literary conference. Grady is visited by his agent (Robert Downey Jr.), and various aspects of his life all come to a head at the same time.

The film boasts one of Michael Douglas’ better late-period performances – a role for which the then 55-year-old actor reportedly put on weight and left behind his traditional handsomeness. After Wonder Boys and Traffic later that year, Douglas wouldn’t have another starring role of consequence until Solitary Man, nine years later.

Beyond Wordfest

The plot of Wonder Boys mostly concerns a series of adventures between Tripp and a strange undergraduate named James (a pre-Spidey Tobey Maguire), which involve a gun, a dead dog, a jacket that once belonged to Marilyn Monroe, and various other silliness. Also around is Katie Holmes as Hannah, a student with the hots for Grady. James, in particular, is a true cinematic original – gay, depressive, possibly autistic, a pathological liar, and prone to reciting the dates and causes of death of every Hollywood suicide ever.

Neil Young’s “Old Man” (“Old Man take a look at my life/I’m a lot like you were”) appears on the soundtrack of Wonder Boys, along with Bob Dylan’s “Things Have Changed” and John Lennon’s “Watching the Wheels,” and while that might appear on the nose, this is a film about an older man looking back on life, and all the things he regrets.

Though of course, those who base their entire understanding of movies around the MCU remember Wonder Boys as the movie where Iron Man (Downey) and Spider-man (Maguire) have a gay affair.

Dog Days

Like so many other movies made between 1995 and 2005, there’s a scene where the lead character gets into a physical confrontation with a dog. What was it about entertainment during that period, with its blasé treatment of the violent death of dogs? In “Rent,” Angel shot a dog for money and nonetheless emerged as the moral center of the piece. And wouldn’t people smell the dead dog that’s being carried around for the entire movie?

The film also features the character of Antonia Sloviak (Michael Cavadias), a cross-dresser who arrives on the plane with Downey, but is soon ditched by him, and is seen removing makeup in anticipation of meeting family. It’s a nifty little character arc for someone with about five minutes of screen time.

One of Hanson’s best

Wonder Boys was directed by Curtis Hanson, in the middle of his most successful period, as the film was released in between L.A. Confidential (1997) and 8 Mile (2002). Unlike those films, Wonder Boys was notoriously a flop. It was, however, nominated for Academy Awards for writing and original song, and won one, for Bob Dylan’s song “Things Have Changed.”

Hollywood has mostly left Chabon’s work on the table…

Following Wonder Boys‘ lack of financial success, Hollywood has mostly left Chabon’s work on the table, leaving such novels as Pulitzer-winning The Amazing Adventures of Kavalier and Clay and The Yiddish Policeman’s Union tragically unadapted. Instead, Chabon has gone Hollywood himself; he’s currently the showrunner of Star Trek: Picard.

Legacy of Wonder

There aren’t many movies like Wonder Boys anymore, and its flop may be one reason why. But this sort of small human story, featuring a lineup of strong actors, is the sort of thing I’d like to see Hollywood get back to making, along with some of Michael Chabon’s other novels.