By “The Film Nest” guest contributor Chase Kahn (see him in the comments section as well).

“A worried man with a worried mind”, croons an aged Bob Dylan over the opening credits, voice raspier than ever. Michael Douglas plays a struggling writer and literary professor in the midst of a serious life crisis. His wife has just left him, he can’t finish his second novel and he’s in love with the chancellor of the university; her husband also happens to be head of the English department.

In between making early 90’s thrillers (The Hand That Rocks the Cradle, The River Wild) and venturing into contemporary Nancy Meyers territory (In Her Shoes, Lucky Me), Curtis Hanson peaked in 1997 with his neo-noir police saga L.A. Confidential. He would follow it up three years later with his 2000 box-office flop Wonder Boys, an exceptional yet underrated and seldom seen film that grossed a mere $19 million domestically. Even with a solid backing by most critics at the time, for whatever reason, the movie never caught on significantly with audiences or awards-season voters, catching just a screenplay, editing and best song nomination at the Oscars.

Douglas plays said professor and novelist Grady Tripp, in love with the aforementioned school chancellor (Frances McDormand) and a mentor to students James Leer (Tobey Maguire) and Hannah Green (Katie Holmes). All the while, he’s hassled by his editor (Robert Downey Jr.) who needs Grady to finish his book as badly as Grady does – for reputations’ sake. To make matters worse, Grady’s most troubling student – the brilliant but reserved James Leer – has just shot his boss’s dog to death at a party, which now finds its resting place in the back of Grady’s 1966 Ford Galaxy.

Michael Douglas as Grady Tripp, a worried man, indeed.

Wonder Boys is essentially a darkly comic ensemble film about finding your purpose, taking action and pushing forward to achieve it – don’t sit idle wallowing in your daily routine. This notion is mirrored in Grady’s unfinished novel, which is pushing 3000 pages without an end in sight. Grady doesn’t have writer’s block, as he describes, he just, “can’t stop.”

It’s also very much fundamentally about the relationship between Grady (Douglas) and his most talented yet troubled student James (Maguire). Hated by his fellow students and quietly “spooky”, he makes his home out of a bus station, snacking on cheese sandwiches out of the vending machine for food. One day, while “rescuing” James from his grandparent’s basement, Grady and his editor, Terry (Robert Downey Jr.) run into a freshly typed paragraph still rolled around the typewriter. “His heart, once capable of inspiring others so completely could no longer inspire so much as itself. It beat now only out of habit,” it reads. Grady isn’t rescuing James, James is rescuing him.

No, Spider-Man is not a part of "The Avengers," sorry.

Douglas finds the twisted ironic center of this character and brings real emotion and humor to him. His filthy and tainted pink robe and leathery, wrinkled brows depict the years of stagnant progression, or lack there of, that have taken a toll on his life which is now clearly in its latter half. In fact, everybody in the cast is great. Before becoming Peter Parker, Tobey Maguire is fantastic here, his blank expression speaking louder than words ever could. Robert Downey Jr. shortly displays the eccentric humor and talent that he would later carry into works like Zodiac and Iron Man. Rip Torn, Frances McDormand and a “Dawson’s Creek” Katie Holmes all supply adequate weight to their respective roles, as well.

Wonder Boys is based on Michael Chabon’s novel of the same name, which was loosely based on his life and a professor he had in college named Chuck Kinder, who also had an inordinately long, unfinished novel. Chabon himself also took seven years in-between 1988’s “Mysteries of Pittsburgh” (his debut) and 1995’s “Wonder Boys”, the exact same amount of time that it’s been since Grady’s debut novel won the PEN award.

An amazing writer, Chabon is also very clearly a movie fan. In addition to references to Errol Flynn and Marilyn Monroe here, in his 2007 novel, “The Yiddish Policemen’s Union”, his alternate history sees Orson Welles finishing his elusive “Hearts of Darkness”, something only a die-hard film fan would ever dream of. I’m sure someone like Chabon would find a lot of like here in Wonder Boys, a real hidden gem.

Buy this Films U Missed here.