“…fantastically-clever and well-told dark comedy that takes on the spirit of a classic novel…”

Over the weekend, I spent the night in a cozy bed and breakfast in Indianapolis owned by Gary Hofmeister. Being a lover of film himself, the Old Northside Bed & Breakfast boasts an extensive collection of good, old-fashioned VHS tapes in all their glory. Perhaps I was in need of a cinematic palate-cleanser after choking down one of the worst films I’ve ever seen (Pixels) on Friday (and I once forced myself to watch a whole ten minutes of Ankle Biters 2002, so that’s really saying something). Anyhow, an older, classic film was in order, and Wonder Boys (directed by Curtis Hanson, 2000) seemed to be just the thing. It’s hard to believe that a film this special could have flown under my radar for the last 15 years, but maybe it needed to so that I could truly appreciate how special this one was. Being an English graduate as well as a lover of all things literary, this one hit home for me. Wonder Boys is a fantastically-clever and well-told dark comedy that takes on the spirit of a classic novel while simultaneously entertaining as a good movie should.

“Writing a book is a horrible, exhausting struggle, like a long bout of some painful illness. One would never undertake such a thing if one were not driven on by some demon whom one can neither resist nor understand.” –George Orwell. A writer is often a sensitive, emotional, and tortured soul. Unfortunately for Professor Grady Tripp (played by Michael Douglas), he is tortured by much more than his inability to complete his second novel. His wife has left him…again, and his editor Terry Crabtree (played by Robert Downey Jr.) is in town. With his novel now seven years in-the-making, Grady feels the pressure. His affair with Dean Sara Gaskell (played by Frances McDormand) also complicates things, as she is married to Walter Gaskell (played by Richard Thomas) who just happens to oversee the English department. While one of Grady’s students, Hannah (played by Katie Holmes) is yearning for his attention physically, another’s undeniable talent yet curiously-dark personality yearns for his attention as a mentor and teacher. When this strange, young talent named James Leer (played by Tobey Maguire) is drawn out of his shell, Grady will find himself scrambling to clean up one mess after another as their situation spins comically out of control.

Before Michael Douglas protected the president in The Sentinel or mentored a hero in Ant-Man, there was Wonder Boys. Tobey Maguire had not yet ridden to glory in Seabiscuit nor had he swung from building to building in Spiderman. Katie Holmes was pre-Tom Cruise, and Robert Downey Jr. was pre-Iron Man. Watching these actors together under one director so many years ago is an absolutely incredible experience. Tobey Maguire playing a troubled, young writer, plagued by a dark inability to socialize with his peers, was surprisingly well-done and deep. The tit-for-tat between he and Michael Douglas was well-timed and playful, and their chemistry felt natural and effortless. Michael Douglas’s character was also troubled by his own emotional demons, and his portrayal of Grady Tripp was quite possibly one of his greatest performances, landing him a Golden Globe for it in 2001.

The ploy plays itself out carefully, as if reading a novel in which every turn of the page reveals a little more about the characters you think you might know. Although, here, the characters themselves are as strange as they are mysterious and interesting. It’s a fascinating journey down the rabbit hole, only this time, Alice happens to be an aging Literature professor and published author afraid of becoming a washed-up has-been. While Wonder Boys is an intelligent and quirky peek into the sometimes twisted mind of a writer, it is also a fun series of unfortunate events that will keep you guessing what could possibly happen next. Despite being over a decade old, this film holds up well. If you’re looking for a time hop back to a film with warm performances and an interesting story, Wonder Boys is well worth your time. This one wins a 9/10 from me. I might even give the novel by Michael Chabon a read, because it really is a good story.