Michael Douglas plays GRADY TRIPP, a college professor trying to write his second novel, seven years after his first one was a huge success. He is stuck in one heck of a writers block. The more he writes, the further away the ending becomes. He's now up to page 2612 with no end in sight, and spends most of his day smoking pot.
He is also having an affair with SARA (Frances McDormand), the wife of his boss WALTER (Richard Thomas), (that's right... John-boy from the Waltons) Sara is also pregnant with Douglas' child, and Douglas' wife has left him.
At a party for visiting writers at Sara's house, he befriends Tobey Maguire. A depressed and habitually lying student of his. He shows Tobey, Walter's memorabilia collection including the coat Marilyn Monroe wore on her wedding day to Joe Dimaggio.
When leaving the party, Douglas is attacked by Walter's dog and in a panic, Tobey shoots and kills the dog. Tobey steals the Marilyn coat, by stuffing it in his backpack.
Robert Downey Jr plays TERRY CRABTREE, Douglas' bisexual editor who desperately needs a hit book to publish or will lose his job. He keeps pressuring Douglas to finish his book.
Robert Downey Jr. and Tobey spend the night together and Downey falls in love with the novel that Tobey has written and wants to publish it.
Walter figures out that Tobey is the guy that shot his dog and stole the Marilyn coat. He has him arrested.
Douglas' car that was given to him turns out to be a stolen car. It gets stolen back by the original owner (with Tobey's backpack inside it.)
Douglas, along with Downey Jr, figure that if they can retrieve the coat, it will get Tobey off. They along with Douglas' 2612 page manuscript (I'm still not sure why they took it) track down the car but the backpack is empty. The owner shows up along with his girlfriend (wearing the coat). Downey Jr tries to stop the owner from shooting Douglas but crashes his car, sending all of Douglas' pages, flying into the river.
Douglas decides to let the girl keep the coat, and told Downey Jr to figure another way to get Tobey out of jail.
Cut to the College's writing award assembly, hosted by Walter announcing all the area writers that are about to be published.
Among them is Tobey. He will be published by Downey Jr. How come Walter didn't press charges? Because Downey Jr is also going to publish Walter's book on the marriage of Joe Dimaggio and Marilyn Monroe.
We now shift to a year later. Douglas is all cleaned up, no longer working at the college. He seems happy as he writes on his computer. A car pulls up and it is Sara with their daughter. Looks like they will all live happily ever after.
Spoiled by: The Movie Spoiler