Having reached the half-century mark of his life, writer and college professor Grady Tripp (MICHAEL DOUGLAS) isn't particularly overjoyed by the way his life is turning out. Despite having written a well-received novel, "Arsonist's Daughter", seven years earlier, he's since been plagued by the uncertainty of being able to match its success, thus resulting in a follow-up novel that's now more than 2,600 pages long.
To make matters worse, his third wife has left him, he's in love with the university's chancellor, Sara Gaskell (FRANCES McDORMAND) -- who happens to be married to his boss, Walter (RICHARD THOMAS), the chairman of the English department -- and a strange fellow, Vernon Hardapple (RICHARD KNOX), seems unnaturally fixated on his car.
While his students, including Hannah Green (KATIE HOLMES), who's renting a room in his house, and James Leer (TOBEY MAGUIRE), his most talented but misunderstood writer, admire him, Grady is paralyzed by the thought of finishing his novel. Things don't improve then, when his hip but desperate editor, Terry Crabtree (ROBERT DOWNEY JR.), shows up in town supposedly for a three day writer's conference, but is really there wanting Grady's novel.
As if having to deal with all of that, as well as the presence of Q (RIP TORN), a successful and prolific writer, wasn't bad enough, Grady's problems are compounded when James shoots Sarah's dog and then takes a valuable collectible from the Gaskell's home. From that point on and as the police get involved, Grady tries to figure out how to deal with the multitude of problems in his troubled life.