Wonder Boys (2000)

Synopsis: Douglas delivers one of his most compelling performances as Grady Tripp, a disheveled, perpetually adolescent English professor amiably coasting toward a mid-life crisis. On the inaugural day of his university's literary festival, Grady's third wife leaves him and his mistress,... Douglas delivers one of his most compelling performances as Grady Tripp, a disheveled, perpetually adolescent English professor amiably coasting toward a mid-life crisis. On the inaugural day of his university's literary festival, Grady's third wife leaves him and his mistress, university chancellor Sara Gaskell (McDormand), announces that she's pregnant with their child. Her husband Walter (Thomas), the self-absorbed chair of the English department, suspects nothing, but with a baby on the way scandal looms just over the horizon. To further complicate matters, Grady's reckless editor Terry Crabtree (Downey), desperate to revive his flaccid career, flies in from New York to pick up the manuscript for Grady's seven-years-in-the-making follow-up to his critically acclaimed first book -- but at 2612 pages, it remains far from finished. As if that weren't enough to keep him reeling, Grady soon becomes an unwilling accomplice to a canine homicide and the heist of a rare jacket once worn by Marilyn Monroe, both committed by his brightest student -- the languid, slightly pathological James Leer (Maguire). Dressed in a ratty pink bathrobe and driving a stolen car with a dead dog in the trunk, Grady must now find a way to return Marilyn's coat, write the great American novel, nurture James's literary talents, discourage the advances of an amorous co-ed (Holmes), avoid the wrath of a petite James Brown look-alike (Knox), and reconcile with Sara...all before the weekend is over! [More]