Jack Nicholson

At 87 years old, Jack Nicholson has this physical status:

John Joseph Nicholson (born April 22, 1937) is a retired American actor, producer, and screenwriter whose career spanned five decades.

He is best known for his role as a comedian, romance, and grimly comedic representations of anti-heroes and villainous characters.

He played the "eternal stranger, the sardonic drifter" in many of his films, as well as the legal thriller Mars Attacks (1991); the road drama Easy Rider (1969); the neo-noir film The Witches of Eastwick (1979); and the scientific thriller About Schmidt (1994); the science fiction film Itself (1991). Anger Management (2003); the romantic comedy Something's Gotta Give (2004); and the crime drama The Departed (2006).

He has also directed three films, including The Two Jakes (1990), the sequel to Chinatown. Nicholson's 12 Academy Award nominations make him the most nominated male actor in the Academy's history.

Both actor for drama One Flew Over the Cuckoo's Nest (1975) and another for the romantic comedy As Good as It Gets (1997).

He also received the Academy Award for Best Supporting Actor for the comedy-drama Terms of Endearment (1983).

He is one of only three male actors to win three Academy Awards and one of only two actors (alongside Michael Caine) to be nominated for an Academy Award for acting in every decade from the 1960s to the 2000s.

He has received six Golden Globe Awards and the Kennedy Center Honor in 2001.

He was one of the youngest actors to be nominated for the American Film Institute's Life Achievement Award in 1994, at 57. Nicholson had a variety of high-profile relationships, most notably with Anjelica Huston and Rebecca Broussard, and she was married to Sandra Knight from 1962 to 1968.

He has five children, one with Knight, two with Broussard (including Lorraine Nicholson), and one with Susan Anspach and Winnie Hollman.

Early life, education, and military service are all related.

John Joseph Nicholson was born in Neptune City, New Jersey, the son of a showgirl, June Frances Nicholson (stage name June Nilson, 1918-1993). Nicholson's mother was of Irish, English, German, and Welsh descents. Nicholson has compared himself to playwright Eugene O'Neill, who appeared in the film Reds, saying, "I'm not saying I'm as black as he was." His mother married Italian-American showman Donald Furcillo (1909–1997) before realizing that he was already married. Patrick McGilligan argued in his book Jack's Life that latish-born Eddie King (originally Edgar A. Kirschfeld) June's boss may have been Nicholson's biological father rather than Furcillo. According to other reports, June Nicholson was uncertain of the father's identity. Nicholson's parents decided to raise him as their own child without revealing their true parentage, despite June's appearance as his sister. Time magazine researchers learned that his "sister," June, was actually his mother, and that his other "sister," Lorraine, was really his aunt. Both his mother and grandmother died by this time (in 1963 and 1970, respectively). Nicholson said it was "a pretty dramatic occurrence, but it wasn't what I'd call traumatizing." "I was really well developed psychologically."

Nicholson grew up in Neptune City. 7 He was born in his mother's Roman Catholic Church. His family had lived in Spring Lake, New Jersey, before starting high school. 16 "The family moved one more -- this time two miles south to Spring Lake, New Jersey's so-called Irish Riviera, where Ethel May's grandmother, Ethel May, established her beauty parlor in a rambling duplex at 505 Mercer Avenue." "Nick" as he was known to his high school classmates at Manasquan High School, where he was voted "Class Clown" by 1954. He was in detention every day for the entire school year. In his honor, he was given a theatre and a drama award at the university. Nicholson and his aunt Lorraine attended his 50-year high school reunion in 2004.

Nicholson joined the California Air National Guard in 1957, in a move he often referred to as a "dodge the draft"; the Korean War–era's Military Selective Service Act was still in place, and draftees were required to complete up to two years of active service. Nicholson, a firefighter assigned to the unit based at Lackland Air Force Base, underwent basic training at the Van Nuys Airport. Nicholson was called up for several months of extended service during the Berlin Crisis of 1961, and he was suspended at the time of his enlistment in 1962.

Personal life

Nicholson is well-known for his inability to "settle down" in his personal life, with a spot on Maxim's "Top Ten Living Legends of Sex" list. He has fathered six children by five women but married only once. Although Nicholson's marriage was to Sandra Knight of The Terrorist from 1962 to 1968, they separated in 1966. There was just one child in the family.

Susan Anspach, a co-star on Five Easy Pieces, argued that Nicholson conceived Caleb, a 1970s baby, was fathered by her son Caleb. Nicholson said he wasn't sure he was Caleb's father in 1984, but Caleb said Nicholson had acknowledged him as his son in 1996. Nicholson sponsored Caleb's college tuition between 1988 and 1994. Around 1998, Nicholson finally acknowledged Caleb as his son and said that they would get along "beautifully now." Caleb's "son, whose father is Jack Nicholson," according to Anspach's New York Times obituary.

Nicholson was in a love with singer Michelle Phillips, ex-wife of his best friend Dennis Hopper's children, during which she suffered a miscarriage. Nicholson's longest friendship was with actress Anjelica Huston, from 1973 to 1990. Their on-again, off-again romance included several points of similarity with other women, including former Bond girl Jill St. John and Danish model Winnie Hollman, with whom Nicholson allegedly fathered a daughter but Nicholson has never revealed it publicly.

When Nicholson had an affair and fathered a child with actress/waitress Rebecca Broussard, the relationship came to an end. They had two children: Lorraine, 1990, 1990, and Raymond, 1992. Nicholson and Broussard split up in 1994; in August, Nicholson reportedly had a daughter with waitress Jeannine Gourin. Nicholson has never revealed the child in a public forum.

Nicholson joined actress Lara Flynn Boyle in the late 1990s. The two siblings split up in 2000, later reuniting before splitting permanently in 2004, after which Nicholson was introduced to English supermodel Kate Moss. Nicholson dated actress Paz de la Huerta, who is 47 years old, in 2006.

Children, "give your life a sense of meaning that it can't have without them," Nicholson said. "I give unconditional love." "I didn't get enough of my eldest daughter because I was trying to make a living," he said.

Robert Blank said in a criminal lawsuit filed on February 8, 1994, Nicholson, then 56, assaulted Blank's Mercedes-Benz while he was stopped at a red light in North Hollywood. Nicholson used a golf club to bash the roof and windshield of Blank's car after accusing Blank of cutting him off in traffic. Blank's account of the incident and misdemeanor charges of assault and vandalism against Nicholson was confirmed by a witness. After Nicholson apologised to Blank, charges were dropped, and the two sides signed an undisclosed deal, which included a $500,000 check from Nicholson.

A complaint was brought against Nicholson in 1996 for rupturing a woman's breast implants. Catherine Sheehan's first lawsuit was brought against him later this year, alleging that he begged a woman named Catherine Sheehan $1,000 for sex and then assaulted her as she tried to retrieve the money. Sheehan was offered a $40,000 settlement but brought another one against him, arguing that the agreement was insufficient to compensate the injuries she sustained, including brain injury, which she described as "actually killing her." The lawsuit was dismissed.

Nicholson was housed on Mulholland Drive in Beverly Hills for a number of years. Warren Beatty was born in Burbank, Ontario, and he was best known as "Bad Boy Drive" on the road. Nicholson bought his bungalow for $6.1 million in 2004, with the intention of having it demolished. Nicholson said he did so out of respect for Brando's legacy, because it had become prohibitively costly to renovate the "derelict" building, which had been plagued by mold.

In Thompson's autobiography Kingdom of Fear, Nicholson's friendship with author-journalist Hunter S. Thompson is chronicled. After Thompson died in 2005, Nicholson and fellow actors Johnny Depp, John Cusack, and Sean Penn attended his private memorial service in Colorado. Nicholson was also a close friend of Robert Evans, the producer of Chinatown, and after Evans lost Woodland, his home, as a result of a 1980s heroin bust, Nicholson and other Evans friends bought it back to Woodland. Danny DeVito and Joe Pesci, both from New Jersey, are all good friends.

Nicholson is a huge fan of the New York Yankees and the Los Angeles Lakers. Since 1970, he has been a Lakers season ticket holder and has been selling courtside season tickets for the past 25 years, both at The Forum and Staples Center, missing very few games. In a few instances, Nicholson has debated with game officials and opponents, as well as walking into the courthouse. Since screaming at a referee, he was almost banned from a Lakers playoff game in May 2003. Nicholson, the former Lakers star, died in a helicopter crash in January 2020, and he spoke directly with Los Angeles station KCBS-TV to express his sadness.

Nicholson is a collector of twentieth-century and contemporary art, including works by Henri Matisse, Tamara de Lempicka, Andy Warhol, and Jack Vettriano. Nicholson has "one of the finest collections out here," artist Ed Ruscha said in 1995.

Although Nicholson has referred to himself as a "lifelong Irish Democrat," he has said he supports every president. In 2020, Nicholson endorsed Bernie Sanders for president. Though he is opposed to abortion, he is pro-choice. "I'm pro-choice but against abortion because I'm an illegitimate child myself, and taking another position would be hypocritical." I'd be dead, but I'd be dead. "I wouldn't exist" if I didn't exist. He has also expressed admiration, gratitude, and admiration for the women who made the decision in their individual case.

"I don't believe in God now," Nicholson said during a 1992 Vanity Fair interview. I can still have a lust for someone with faith. I can imagine how that could be a deeply relaxing experience."

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Career

Nicholson first came to California in 1950 to visit his sister. William Hanna and Joseph Barbera, a MGM cartoonist, worked as an office worker for animation designers. They offered him an entry-level job as an animator, but he turned down, citing his desire to become an actor. He recalled that his first day as a working actor (on Tales of Wells Fargo) was May 5, 1955, which he considered lucky, as 5 was the jersey number of his boyhood idol, Joe DiMaggio. He trained to be an actor with the Players Ring Theater, but after that, he found small parts on stage and in TV soap operas, he became a director. In the film version of The Cry Baby Killer (1958), he made his film debut in a low-budget teen drama. Nicholson used to film with Roger Corman, a film maker. Corman directed Nicholson on several occasions, including in The Little Shop of Horrors as a masochistic dental patient and undertaker, Wilbur Force, where he plays an evil ghost in The Raven; The Terror, where he plays a French officer seduced by an evil ghost; and The St. Valentine's Day Massacre. Nicholson worked on low-budget westerns with director Monte Hellman; two of them, Ride in the Whirlwind and The Shooting, attracted little attention from American film producers, but the French art-house circuit soon became popular on television, and the series was later sold to television. In the 1960 film The Wild Ride, Nicholson appeared in two episodes of The Andy Griffith Exhibition and starred as a nascent dirt-track racer.

Nicholson seemed to be resigned to a life as a writer/director with his acting career floundering. His first real attempt at writing was the screenplay for the 1967 counterculture film The Trip (directed by Corman), starring Peter Fonda and Dennis Hopper. Fonda told Nicholson that the writing was thrilling and that it might become a good film after first reading the script. Fonda was dissatisfied with the film's outcome and blamed the editing for turning it into a "predictable" film, despite mentioning it publicly. He remembers, "I was livid." Nicholson co-wrote with Bob Rafelson, the film Head, and also arranged the film's soundtrack.

When a role in Fonda and Hopper's Easy Rider (1969), Nicholson's first big acting break came as a result. George Hanson, an alcoholic, received his first Oscar nomination. The film only cost $400,000 to make, and it became a blockbuster, grossing $40 million. Nicholson's interpretation of his role, according to biographer John Parker, put him in the company of earlier "antihero" actors, such as James Cagney and Humphrey Bogart, while campaigning him to be a "overnight number one hero of the counter-culture movement." For Nicholson, the role was a lucky break. Rip Torn, the role had been planned but he was forced to leave the project after an argument with Hopper. "All I could see in the early films before Easy Rider was this poor young actor struggling to get out of the screen and have a film career," Nicholson later stated. Stanley Kubrick, who was captivated by his role in Easy Rider, portrayed Nicholson as Napoleon in a film about his life, but the venture was shelved out partially due to a change in MGM's ownership.

In 1970, Nicholson appeared in Five Easy Pieces alongside Karen Black in what became his persona-defining role. Academy Awards were given to Nicholson and Black for their efforts. Black played Bobby Dupea, an oil rig man, and Nicholson played his waitress mother. In the film, Black noted that Nicholson's character was very different from Nicholson's real one. She said the now-famous restaurant scene had been partially improved by Nicholson and that it was out of character for Bobby, who may not have cared enough to argue with a waitress. "I think Jack has very little in common with Bobby." Bobby seems to have left looking for love. Jack hasn't given up on finding out things because he's so keen on love. Jack is a remarkably intelligent, alive human being. Generally, we're set for a new challenge. "I like listening to everybody," Nicholson said in an interviewer. To me, this is the elixir of life."

Black later admitted that she had a crush on Nicholson from the time they met, but that they had only met for a short time. "He was so beautiful." He just seemed right at you. I adored him a lot... He really wanted to date me, but I didn't think about him that way because I was going with Peter Kastner... Then I went to do Easy Rider but didn't see him because we didn't have any scenes together... I'm sure he wanted to see him at the premiere but I started weeping. He didn't know it, but it was clear that I loved him a lot, but I didn't know it until I saw him again because it all made sense.

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According to McDougal, Five Easy Pieces became a blockbuster within a month after being announced that September was a leading man and the "new American anti-hero." 130 readers were perplexed as to whether he'd be a new Marlon Brando or James Dean. His work and income increased dramatically as a result. "I have [become] what you so much desired," Trump said. Your name will now be used to describe a product. You'll be Campbell's soup, with thirty-one different roles you can play. "I told his current agent, Sandy Bresler, that he wanted to play people who hadn't existed before, like a 'cusp character,'" he said.

Nicholson appeared in On a Clear Day You Can See Forever in 1970, but the bulk of his performance was left on the cutting room floor. When the film's producer and director, John Boorman, refused to pay what Nicholson's agent wanted, his agent turned down a starring role in Deliverance.

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Nicholson appeared in Carnal Knowledge, a comedy-drama directed by Mike Nichols and co-starring Art Garfunkel, Ann-Margret, and Candice Bergen in 1971. He had been nominated for a Golden Globe Award for Best Actor. "There are James Cagney, Spencer Tracy, Humphrey Bogart, and Henry Fonda," Nichols said. Who else but Jack Nicholson is there after that? Nicholson began a lifelong friendship with Garfunkel during the filming. Garfunkel stayed at Nicholson's home in a room that Nicholson jokingly described as "the Arthur Garfunkel Suite."

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Hal Ashby's The Last Detail (1973), with Randy Quaid, for which Nicholson received Best Actor at the Cannes Film Festival and was nominated for his third Oscar and a Golden Globe, among other Nicholson roles. David Gilmour, a television journalist, writes that one of his favorite Nicholson scenes from his films was the one in which Nicholson slaps his rifle on the bar screaming he was the Shore Patrol. Roger Ebert called it a good film but praised Nicholson's performance as the primary reason: "He makes a character so complete and complicated that we should avoid worrying about the film and instead wait to see what he does next."

Nicholson appeared in Roman Polanski's noir thriller Chinatown in 1974 and was nominated for the Academy Award for Best Actor for his role as Jake Gittes, a private detective. Faye Dunaway and John Huston appeared in the film, as well as a cameo role for Polanski. Nicholson's portrayal in One Flew Over the Cuckoo's Nest was sharp-edged, menacing, and combative, a character with knowledge of "how to go over the top." That part prevented Chinatown from being a typical genre crime film. In addition, Ebert emphasizes the significance of Nicholson's career, seeing it as a major departure from the previous decade's exploitation films. "As Jake Gittes, he stepped into Bogart's shoes," Ebert says. "As a man attracted to audiences because he suggests both comfort and danger." Nicholson, a Gittes forward, invented the persona of a man who had seen it all and was also capable of being amused."

Long before Polanski's wife, Sharon Tate, was murdered by the Manson Family, Nicholson was acquainted with him and helped him during his funeral. 109–110 After Tate's death, Nicholson began sleeping with a hammer under his pillow and took time off work to attend Manson's trial.

Polanski was arrested at Nicholson's home for the sexual assault of 13-year-old Samantha Geimer, who was modeling for Polanski during a magazine photo shoot around the pool in 1977, three years after Chinatown. At the time, Nicholson was out of town filming a film, but actress Anjelica Huston had dropped by unannounced to pick up some items. "We'll be right out," Polanski in the other room said. Polanski stepped out with Geimer and welcomed her to Huston, where they chatted about Nicholson's two big dogs, who were sitting nearby. Geimer had platform heels and looked quite tall, according to Huston. Polanski had packed up his camera gear and Huston saw them leave in his car after a few minutes of banter. After Polanski was arrested, Huston told police that she had "nothing wrong" and that she had never seen them together in the other room.

Afterward, Geimer learned that Huston wasn't meant to be at Nicholson's house that day because they'd recently broken up, but they did stop over to pick up some things. Neimer described Nicholson's house as "definitely" a guy's house, with a lot of wood and shelves stuffed with photos and mementos.

Randle P. McMurphy was one of Nicholson's greatest contributions in 1975, as he appeared in One Flew Over the Cuckoo's Nest. Milo Forman and co-produced Michael Douglas's film was an adaptation of Ken Kesey's novel of the same name. Nicholson is an anti-authoritarian patient at a mental hospital, where he is a hero to the other patients. Danny DeVito played in a young age. Afterward, Nicholson discovered that DeVito grew up in the same city of New Jersey as well as many of the same people. The film received nine nominations at the Academy Awards, five of which were for Best Actor, including Nicholson's first.

Nicholson's job was a success, with biographer Ken Burke noting that his "smartass demeanor balances his genuine concern for his fellow patients' care, as well as his empathetic spirit, which was too free to exist in a repressive social system." Nicholson was encouraged to perform throughout the film, including the majority of the group therapy sequences. Marie Brenner, a 273 reviewer, writes that his bravura performance "transcends the screen" and incites other actors by brightening their mental disorders by his comedic dialogue.

She describes his performance:

In 1975, Nicholson appeared in Michelangelo Antonioni's The Passenger (1975), which co-starred Maria Schneider. Nicholson plays David Locke, a journalist who on a North African assignment, decides to abandon journalism and seeks to escape by adopting a new assumed identity. Sadly, the deceased man whose identity he takes on turns out to be a weapons smuggler on the run. Antonioni's strange plot featured convincing dialogue and fine acting by a state film critic Seymour Chatman. It was shot in Algeria, Spain, Germany, and England.

The film received rave feedback and re-established Antonioni's reputation as a great producer. He wanted the film to have more of a "spy feeling [and] be more political." According to Judith Crist, Nicholson started shooting the film from an unfinished script, but upon its completion, he thought so highly of it that he bought the world rights and film recorded a reminiscence of working with Antonioni. Penelope Gilliatt, a critic and screenwriter, gives an insight into Nicholson's role: a critic and screenwriter.

He continued to perform more interesting roles. He appeared in The Last Tycoon opposite Robert De Niro. He played a less sympathetic role in Arthur Penn's western The Missouri Breakers (1976), specifically in his interactions with Marlon Brando. Nicholson was particularly inspired by Brando's acting talent in his youth as an assistant manager at a theater, and he's recalled that he watched On the Waterfront about 40 times. "I'm one of the first generation that revered Marlon Brando," he said.

Nicholson has stated that although De Niro and Brando were praised for their abilities as method actors, he himself hasn't been described as one: "I'm still fooling them," he told Sean Penn. "I think it's an achievement because there is obviously no one who knows Method better academically than I do," says the author, or actually uses it more in his work. But it's funny, because no one really knows what it is. It's both perception and reality, I guess."

Despite the fact that he received no Academy Award for Stanley Kubrick's adaptation of Stephen King's The Shining (1980), Jack Torrance's appearance in the film as a writer remains one of his finest contributions. He was Kubrick's first attempt to act in the role, but the book's author, Stephen King, wanted more of a "everyman." Kubrick won the argument and called Nicholson's behavior "on par with the greatest actors of the past," including Spencer Tracy and Jimmy Cagney. Nicholson drew on his own experience as a writer and slept short hours to help avoid being in an agitated state during the shooting. Shelley Duvall, Nicholson's co-star, recalled that she and Nicholson spent many hours discussing their characters, with Nicholson arguing that his character was cold to her right from the start. Nicholson was always on target, and Kubrick was always on target, and if Kubrick was confident that Nicholson knew his lines well enough, he encouraged him to improvise outside of the script. 434 Nicholson, for example, improvised his now-famous "Here's Johnny" to become a hit on the radio. : : 433, as well as a scene in which he unleashes his rage on his wife when she interrupts his work. 445 Due to Kubrick's impeccableionism, there have been several takes of scenes. Nicholson fired a scene with the ghoulish bartender 36 times. "Stanley's demanding," he said. He'll be on a fifty-fold role, and you'll have to be on top of it.

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In 1982, he appeared as an immigration enforcement agent in The Border, directed by Tony Richardson. Warren Oates, a corrupt border official, co-starred on the film. Richardson wanted Nicholson to play his part less expressively than he had in his previous roles. He told him, "Less is better," and he wanted him to wear reflecting sunglasses to represent what patrolmen wore. Richardson recalled that Nicholson had worked hard on the set: 318 Richardson recalled.

In Terms of Endearment (1983), directed by James L. Brooks, Nicholson received his second Oscar, an Academy Award for Best Supporting Actor. Shirley MacLaine and Debra Winger appeared in the film. McGilligan believes it was one of Nicholson's most nuanced and memorable characters. He and MacLaine performed many of their scenes in a variety of ways, always testing and making changes. According to McGilligan, the film had a "buoyant edge" as a result of Nicholson's performance as "Jack floating like a butterfly."

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Nicholson continued to work in the 1980s, starring roles including: The Postman Always Rings Twice (1981), where Nicholson depicts writer Eugene O'Neill with a quiet intensity; The Witches of Eastwick (1987); and Ironweed (1987). (Reds, Prizzi's Honor, and Ironweed were among the Oscar nominations that followed.) "He just illuminates the book," John Huston, who wrote Prizzi's Honor, said of Nicholson's acting. In one scene after another, he impressed me; the film is made largely of first takes with him."

Nicholson played the Joker, the psychotic villain, in the 1989 Batman film. The film was a huge success worldwide, and a lucrative deal gave him a piece of the box office revenue estimates, which was between $60 million and $90 million. "I was very proud" of his Joker appearance: "I consider it a work of pop art," Nicholson said.

Nicholson received yet another Academy Award nomination for his role as hot-headed Col. Nathan R. Jessup (1992), a film about a massacre in a US Marine Corps unit. According to one review, his performance was "spellbinding," adding that he portrayed "the essence of the quintessential military mindset." Nicholson's character "burned and roared," critic David Thomson says. Rob Reiner, the film's director, discusses how Nicholson's acting experience influenced the other actors during rehearsals: "I had the privilege of seeing Jack Nicholson there." He knows what he's doing, and he comes to play, every time out, with a full show! 'Oooooh, I better get to my game here because this guy's coming to play,' it says to a number of the other actors. So I can't hold back; I've got to come up to him.' "He sets the tone."

Nicholson worked with Batman director Tim Burton on Mars Attacks once more, bringing two characters, President James Dale and Las Vegas property developer Art Land, together. Warner Bros. studio executives disliked the prospect of killing off Nicholson's character, so Burton created two characters and killed them both off.

Not all of Nicholson's performances have been well-received. He was nominated for Razzie Awards as the worst actor for Man Trouble (1992) and Hoffa (1992). However, his role in Hoffa earned him a Golden Globe nomination. Since Nicholson portrayed one of his best screen characters, namely, someone who is "snarly, dumb, noble, rascally," all the parts of 'Jack' are terribly neglected, David Thomson claims that the film was terribly neglected.

In the romantic comedy As Good as It Gets (1997), Nicholson's third film directed by James L. Brooks, he received his next Academy Award for Best Actor. Melvin Udall, a "wickedly funny" mean-spirited novelist with a chronic illness of obsessive-compulsive disorder, was an actor. "I'm a Studio Method actor," he said. "I was prone to give some sort of clinical description of the disorder." Helen Hunt, a single mother in Manhattan, was matched for the Academy Award for Best Actress, a frequent diner in the restaurant where she works as a waitress. The film was a box-office smash, grossing $314 million, making it Nicholson's second best-grossing film after Batman.

Nicholson admits he initially disliked playing a middle-aged man alongside a much younger Hunt, seeing it as a movie cliché. "But Helen was disarmed at the first meeting," he says, "and I stopped worrying about it." They got along fine during filming, with Hunt saying that he "treated me like a queen" and that they immediately understood: "It wasn't even what we said" she said. "It was just a time we both had to tune into that was extremely convenient." Nicholson was "in rare form," according to Newsday's Critic Jack Mathews, "it's one of those performances that make you wonder how much fun the actor is having." Their on-screen relationship, according to author and screenwriter Andrew Horton, is like "fire and ice, oil, and water—complete opposites." Nicholson, the first actor to be honoured with the Stanislavsky Award at the 23rd Moscow International Film Festival in 2001 for "conquering the heights of acting and faithfulness."

In 2001, Nicholson appeared in The Pledge, a drama in which he portrays former police detective Jerry Black, who has promised to locate a young girl's killer. Nicholson was lauded for his appearance; Bob Graham of the San Francisco Chronicle called it "deeply felt" compared to some of Nicholson's other films. Nicholson portrayed a Nebraska, Nebraska, actuary who doubted his own life after his wife died in About Schmidt (2002). His quiet appearance earned him the Academy Award Nomination for Best Actor. He played an affront therapist who was hired to support an overly pacifist man (Adam Sandler) in Anger Management (2003). Nicholson appeared in Something's Gotta Give as an aging playboy who falls for his young mother (Diane Keaton) in 2003.

In late 2006, Nicholson returned to the dark side as Frank Costello, a nefarious Boston Irish Mob boss based on Whitey Bulger, who was still on the run at the time, in Martin Scorsese's Oscar-winning film The Departed, a retelling of Andrew Lau's Infernal Affairs. Nicholson's performance has received international recognition, as well as numerous accolades and nominations, including a Golden Globe Award for best supporting actor.

In 2007, Nicholson co-starred with Morgan Freeman in Rob Reiner's The Bucket List. Nicholson and Freeman depicted dying men as a result of their list of aspirations. Nicholson conducted the role in Los Angeles, to see how cancer patients coped with their illnesses.

Nicholson's next film role saw him reunite with James L. Brooks, the producer of Terms of Endearment, Broadcast News, and As Good as It Gets, for a supporting role in the 2010 film How Do You Know. Nicholson said in a Vanity Fair article in September that he did not consider himself retired, but that he was now less likely to "be out there."

Nicholson made a special appearance as a host on SNL 40, the 40th anniversary special of Saturday Night Live, on February 15, 2015. Following boxer Muhammad Ali's death on June 3, 2016, Nicholson appeared on HBO's The Fight Game with Jim Lampley for an exclusive interview about his relationship with Ali. He was supposed to be in an English-language remake of Toni Erdmann in 2017, opposite Kristen Wiig, his first film role since How Does It Work?, but everyone, including the director, dropped the initiative.

When asked if Nicholson had been cast in the film in October 2019, producer Mike Flanagan confirmed Nicholson's departure. Nicholson was supposed to make a cameo appearance as another character in the original film but declined to participate in the best cast, crew, and film. Nicholson had been invited to appear in the 2018 film Ready Player One but declined, according to Flanagan.

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