Born on April 22nd, 1937
From Neptune City, New Jersey
South Boston cop Billy Costigan (Leonardo DiCaprio) goes under cover to infiltrate the organization of gangland chief Frank Costello (Jack Nicholson). As Billy gains the mobster's trust, a career criminal named Colin Sullivan (Matt Damon) infiltrates the police department and reports on its activities to his syndicate bosses. When both organizations learn they have a mole in their midst, Billy and Colin must figure out each other's identities to save their own lives.
When aging womanizer Harry Sanborn (Jack Nicholson) and his young girlfriend, Marin (Amanda Peet), arrive at her family's beach house in the Hamptons, they find that her mother, dramatist Erica Barry (Diane Keaton), also plans to stay for the weekend. Erica is scandalized by the relationship and Harry's sexist ways. But when Harry has a heart attack, and a doctor (Keanu Reeves) prescribes bed rest at the Barry home, he finds himself falling for Erica -- who, for once, may be out of his league.
Warren Schmidt (Jack Nicholson) has arrived at several of life's crossroads all at the same time. To begin with, he is retiring from a lifetime of service as an actuary for Woodmen of the World Insurance Company, and he feels utterly adrift. Furthermore, his only daughter Jeannie (Hope Davis) is about to marry a boob. And his wife Helen (June Squibb) dies suddenly after 42 years of marriage.