Robin’s Underrated Gems: Wonder Boys (2000)

Sometimes, no matter how hard it tries, a great movie just cannot become a hit. Such was the case in early 2000 when a quirky little comedy called Wonder Boys was released into cinemas with little fanfare. It drew very good reviews from critics, but failed to draw much money at the box office and disappeared from theatres rather quickly. I went to see it during its original theatrical run and since I was a university student and aspiring writer at the time who completely understood the trials and tribulations of trying to attain a creative writing major, I could totally identify with this film and enjoyed it immensely. Knowing that Wonder Boys would probably be long forgotten by the time next year’s Academy Awards rolled around, the filmmakers made a last-ditch effort to turn the film into a commercial success by lobbying Paramount to give it a theatrical re-release in November of 2000. Once again, it failed to garner a wide audience. Though it did receive nominations for “Best Editing” and “Best Adapted Screenplay”, the only Academy Award the film was able to take home was for its Bob Dylan song on the soundtrack, “Things Have Changed”. I could say that it is tough to explain why Wonder Boys failed to find an audience, but then I realized that it is equally as tough to explain the film’s appeal. As enjoyable as Wonder Boys may be to watch, I can totally understand how it would be a difficult film to market. I guess it’s somewhat ironic that a film about writing would be tough to summarize in words. However, Wonder Boys is definitely one of the best films ever made about writing and anyone who’s ever gone through the ordeal of trying to put their ideas into words on the printed page is sure to identify with this story.

Wonder Boys is based on a 1995 novel by Michael Chabon, and its protagonist is loosely inspired by Chuck Kinder, a colourful professor from the University of Pittsburgh who spent over 20 years obsessively working on a novel whose manuscript wound up growing to more than 3000 pages. In this story, Grady Tripp (Michael Douglas) is an eccentric, dishevelled, pot-smoking creative writing professor at a Pittsburgh university who found great success by publishing an acclaimed novel seven years ago. Grady has been working on another novel ever since then which is yet to be finished and while some people believe that he has lost his touch or developed a serious case of writer’s block, the real truth is that his manuscript has ballooned to over 2600 pages. Grady’s personal life is a bit of a mess as his wife has just left him, and he is involved in an affair with the university’s chancellor, Sara Gaskell (Frances McDormand), who also happens to be married to the head of the English department and has just found out she is pregnant with Grady’s child. In addition, Grady’s gay, equally eccentric editor, Terry Crabtree (Robert Downey, Jr.), has just arrived in town and is just itching for a finished copy of his manuscript, and Grady is also being forced to resist the advances of one of his young female students, Hannah (Katie Holmes), who has developed a major crush on him. As if all this personal drama wasn’t enough, Grady’s weekend soon spirals completely out of control, thanks to one of his students, James Leer (Tobey Maguire), a very odd, brooding young man who happens to be both a brilliant writer and a pathological liar. Grady’s troubles start when James winds up shooting Sara Gaskell’s dog and Grady is forced to help him cover up the incident.

Now, we all know that killing a dog is never the most popular narrative device for an audience, so you know Wonder Boys isn’t going to be a traditional comedy when a dog is shot during its first act and the protagonist spends most of the movie driving around with the dog’s corpse in his trunk. On paper, Wonder Boys seems like your typical coming-of-age story about an older mentor helping out a misguided young protege while learning a lot of valuable life lessons about himself in the process. Technically, that’s exactly what this story is, yet the quality of the writing and acting make Wonder Boys feel completely fresh. Despite all their eccentricities, most of the characters in the film are incredibly likable and fun to watch, and the sharp dialogue by screenwriter Steve Kloves is just a delight to listen to. There are many moments during this film where you think the story is going to settle down into a predictable pattern, yet it usually manages to throw in some offbeat twist that takes things in an unexpected direction. Director Curtis Hanson had just come off of the massive success of L.A. Confidential and many were surprised that he would select his follow-up project to be such a quirky, offbeat, low-key comedy that couldn’t be easily summarized in one sentence. There wasn’t much interest from Paramount to make this film at all until Michael Douglas expressed his enthusiasm for it and agreed to play Grady Tripp for much lower than his usual fee. In my opinion, Douglas has never delivered a better performance and the character of Grady is truly a wonderful creation. With the possible exception of Charlie Kaufman’s Adaptation, I’ve never seen a film that so perfectly captures the life of a writer. The opening scene in the film features some pretentious creative writing students viciously tearing into James’ work, and as someone who was fresh off of taking a creative writing course and encountering students just like this, I knew that this film instantly had me. I could also greatly identify with Grady’s ordeal of starting a story that you don’t how to finish, which causes one to overcompensate by writing something that is excessively long and has no direction. One of the best, most truthful moments in the film is when Hannah starts reading Grady’s mammoth 2600-page manuscript and delicately tries to tell him just how aimless the whole thing is.

While Wonder Boys is Michael Douglas’ film all the way, he gets terrific support from everyone else in the cast. The particular standout is Robert Downey, Jr., and it’s important to remember that this movie was made while he was in the midst of his well-documented substance abuse problems. Downey was on probation during the time he filmed Wonder Boys and while he made it through the entire shoot without any problems, he did wind up violating his parole and getting into more legal trouble not long afterward. However, Downey’s terrific work as Crabtree did help remind the world that even though he had many personal problems, he could still be one of the very best actors in Hollywood. Strong performances like this were definitely instrumental in allowing him to have the opportunity to make his very successful comeback. Incidentally, if you’ve ever wanted to see the future Iron Man and the future Spider-Man in bed together, Wonder Boys is your movie! “Before They Were Stars” aficionados will also enjoy seeing an early performance from Alan Tudyk in the hilarious bit part of a former writing student-turned-janitor who starts a very awkward conversation with Grady about what substances Errol Flynn liked to put on his dick. I think one of the main reasons that Wonder Boys was adapted so well for the big screen was because screenwriter Steve Kloves could identify so well with the material. Kloves had achieved success by writing and directing The Fabulous Baker Boys in 1989, but had fallen into a creative funk and hadn’t worked on a film or written anything for several years before he was hired to adapt Wonder Boys. Of course, Kloves has since found great success by writing the screenplays for seven out of the eight Harry Potter films, but now that the series is over, I’d definitely love to see him try his hand at writing more quirky, character-driven comedies like this. Anyway, I gladly ranked Wonder Boys at #17 in my “Top 25 Favourite Films of the Decade” column, but out of all the films on that list, it’s probably the hardest to recommend to people or to form an adequate explanation of why I like it so much. Film buffs will complain that Hollywood needs less brainless blockbusters and more intelligent, character-driven projects like Wonder Boys, but the unfortunate truth is that films like Wonder Boys just don’t seem to draw large audiences. However, it remains one of the very best films to watch when you’re in the mood to just sit back and relax and enjoy watching the adventures of some very entertaining characters whom you would probably love to hang out with in real life. Incidentally, I just recorded a Shouts From the Back Row podcast about great movie endings and I’m sorry to say that I neglected to mention Wonder Boys, which contains of the all-time best feel-good endings that perfectly summarizes the entire story and its main character.

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