In About Schmidt (2002), Nicholson portrayed a retired Omaha, Nebraska, actuary who questions his own life following his wife's death.
His quietly restrained performance earned him an Academy Award Nomination for Best Actor.
In Anger Management (2003), he played an aggressive therapist assigned to help an over pacifist man (Adam Sandler).
In 2003, Nicholson also starred in Something's Gotta Give, as an aging playboy who falls for the mother (Diane Keaton) of his young girlfriend.
In late 2006, Nicholson marked his return to the dark side as Frank Costello, a nefarious Boston Irish Mob boss, based on Whitey Bulger who was still on the run at that time, presiding over Matt Damon and Leonardo DiCaprio in Martin Scorsese's Oscar-winning film The Departed, a remake of Andrew Lau's Infernal Affairs.
The role earned Nicholson worldwide critical praise, along with various award wins and nominations, including a Golden Globe nomination for best-supporting actor.

In 2007, Nicholson co-starred with Morgan Freeman in Rob Reiner's The Bucket List.
Nicholson and Freeman portrayed dying men who fulfill their list of goals.
In researching the role, Nicholson visited a Los Angeles hospital to see how cancer patients coped with their illnesses.
In About Schmidt (2002), Nicholson portrayed a retired Omaha, Nebraska, actuary who questions his own life following his wife's death. His quietly restrained performance earned him an Academy Award Nomination for Best Actor. In Anger Management (2003), he played an aggressive therapist assigned to help an over pacifist man (Adam Sandler). In 2003, Nicholson also starred in Something's Gotta Give, as an aging playboy who falls for the mother (Diane Keaton) of his young girlfriend. In late 2006, Nicholson marked his return to the dark side as Frank Costello, a nefarious Boston Irish Mob boss, based on Whitey Bulger who was still on the run at that time, presiding over Matt Damon and Leonardo DiCaprio in Martin Scorsese's Oscar-winning film The Departed, a remake of Andrew Lau's Infernal Affairs. The role earned Nicholson worldwide critical praise, along with various award wins and nominations, including a Golden Globe nomination for best-supporting actor.
In 2007, Nicholson co-starred with Morgan Freeman in Rob Reiner's The Bucket List. Nicholson and Freeman portrayed dying men who fulfill their list of goals. In researching the role, Nicholson visited a Los Angeles hospital to see how cancer patients coped with their illnesses.
Jack Nicholson