His buzz far eclipsed that of the film’s heavy-hitting stars, Tom Cruise and Demi Moore. That same year, Nicholson starred as teamster leader Jimmy Hoffa in Hoffa, directed by Danny DeVito. He later reteamed with Michelle Pfeiffer in the thriller Wolf (1994) and starred with Anjelica Huston in Sean Penn’s little-seen directorial debut, The Crossing Guard (1995).

After reprising his role as Breedlove in The Evening Star (1996), the lamentable sequel to Terms of Endearment, Nicholson went on to make two equally disappointing films, including Mars Attacks! (1996) and Blood and Wine (1997), written and directed by Rafelson and co-starring Jennifer Lopez.

The 1997 comedy-drama As Good As It Gets marked a major resurgence for Nicholson, whose performances many critics thought had begun to seem like a caricature of his earlier roles. The film, written and directed by James L. Brooks (Terms of Endearment), starred Nicholson as the obsessive-compulsive novelist Melvin Udall, an immensely unlikable man who is forced to come to terms with his own faults while falling in love with a long-suffering waitress and single mother, played by Helen Hunt. Both Nicholson and Hunt won Academy Awards for their performances, bringing the total number of Nicholson’s Oscars to three—with 11 nominations, he trails only Katharine Hepburn and Streep, who both have 12. In 2000, Nicholson starred in The Pledge, his second collaboration with actor-director Penn. Two years later, Nicholson became an Oscar contender once again for his tour-de-force role in Alexander Payne's About Schmidt. He earned a Golden Globe for his portrayal of a man forced to deal with an ambiguous future as he faces retirement. In 2003, he starred opposite Adam Sandler in the hit comedy Anger Management. Aside from his impressive acting career, Nicholson has also made headlines for the goings-on in his personal life. In 1974, after researching a cover story on the actor for Time, a reporter informed Nicholson that the woman he had thought was his mother (the late Ethel May Nicholson) was actually his grandmother. His mother, June Nicholson, was the person he had known as his older sister; she had died of cervical cancer in the early 1960s, at the age of 43.

Nicholson has also repeatedly made news on account of lawsuits filed against him. In 1996, he was sued for breach of contract by former lover Susan Anspach (his costar in Five Easy Pieces), with whom he allegedly had a son, Caleb.