structural:scholar_edition, information:highlighting, structural:expansion
2000–present: Later roles and retirement

In 2001, Nicholson was the first actor to receive the Stanislavsky Award at the 23rd Moscow International Film Festival for "conquering the heights of acting and faithfulness". That same year Nicholson starred in The Pledge, a mystery drama where he portrays retired police detective Jerry Black, who vows to find a murderer of a young girl. Nicholson was praised for his performance; Bob Graham of the San Francisco Chronicle called it "deeply felt" compared to some of Nicholson's other films. Nicholson acted in Alexander Payne 's comedy-drama About Schmidt (2002), playing a retired Omaha, Nebraska, actuary who questions his own life after his wife dies. His quietly restrained performance earned him nominations for an Academy Award, BAFTA Award, Golden Globe Award and Screen Actors Guild Award for Best Actor. In Anger Management (2003), he played an aggressive therapist assigned to help an overly pacifist man (Adam Sandler). In 2003, Nicholson also starred in the Nancy Meyers directed romantic comedy Something's Gotta Give playing an aging playboy who falls for the mother (Diane Keaton) of his young girlfriend. For his performance he was nominated for the Golden Globe Award for Best Actor – Motion Picture Musical or Comedy. In late 2006, Nicholson marked his return to the dark side in Martin Scorsese's Oscar-winning film The Departed, a remake of Andrew Lau 's Infernal Affairs, playing Frank Costello, a nefarious Boston Irish Mob boss based on Whitey Bulger, who was still on the run at the time. The role earned Nicholson worldwide critical praise, along with various awards and nominations, including a Golden Globe Award for Best Supporting Actor - Motion Picture nomination. In 2007, Nicholson co-starred with Morgan Freeman in Rob Reiner 's The Bucket List, in which 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.

Nicholson is the Hollywood celebrity who is most like a character in some ongoing novel of our times. He is also the most beloved of stars—not even his huge wealth, his reckless aging, and the public disasters of his private life can detract from this... For he is still a touchstone, someone we value for the way he helps us see ourselves.

— David Thomson, a film critic.

Nicholson's next film role saw him reunite with James L. Brooks, director of Terms of Endearment, Broadcast News and As Good as It Gets, for a supporting role for the 2010 film How Do You Know starring Paul Rudd, Reese Witherspoon, and Owen Wilson. The film was a financial and critical failure. In a September 2013 Vanity Fair article, Nicholson said that he did not consider himself retired, but that he was now less driven to "be out there anymore". As of 2023, How Do You Know remains Nicholson's last film role, and brings his filmography to 80 films. In 2013, Nicholson co-presented the Academy Award for Best Picture with First Lady Michelle Obama, the eighth time he presented the Academy Award for Best Picture (1972, 1977, 1978, 1990, 1993, 2006, 2007, and 2013).

On February 15, 2015, Nicholson made a special appearance as a presenter on SNL 40, the 40th anniversary special of Saturday Night Live. After the death of boxer Muhammad Ali on June 3, 2016, Nicholson appeared on HBO 's The Fight Game with Jim Lampley for an exclusive interview about his friendship with Ali. He was reported to be starring in an English-language remake of Toni Erdmann in 2017 opposite Kristen Wiig, his first feature film role since How Do You Know, but the project was later abandoned. In October 2019, with the release of The Shining sequel Doctor Sleep, director Mike Flanagan revealed he approached Nicholson for a cameo appearance, but Nicholson declined with best wishes. Flanagan also disclosed that Nicholson had previously been approached to appear in Steven Spielberg 's science-fiction film Ready Player One (2018).

During an appearance in the November 2, 2023, episode of Marc Maron 's podcast, WTF with Marc Maron, record producer Lou Adler, a longtime friend of Nicholson's, related an anecdote pertaining to the unofficial retirement of the actor, who had not done a film in the 13 years since How Do You Know, saying, "A friend of mine wanted to put him in a movie. And he had a conversation with him. But Jack says, 'I don't want to do it.' He goes, 'You know what I did today? I sat under a tree and I read a book.' That sounds like Jack." Adler stated that Nicholson was "doing whatever he really wants to do," adding, "He wants to be quiet. He wants to eat what he wants. He wants to live the life he wants."