Jack Nicholson’s Dark Side

This article contains references to addiction.

In Hollywood’s pantheon of stars, one name has stood atop the pyramid for decades: Jack Nicholson. Boasting 12 Academy Award nominations and three wins — the most-nominated male actor ever — Nicholson traditionally sat front-row center at the annual award show, flashing his devilish grin while shielding his eyes behind his trademark sunglasses. His performances have become the stuff of Hollywood legend: his breakthrough as a philosophizing alcoholic attorney in “Easy Rider;” rebellious, anti-authoritarian psychiatric patient McMurphy in “One Flew Over the Cuckoo’s Nest;” hard-boiled private investigator Jake Gittes in “Chinatown;” maniacal supervillain the Joker in Tim Burton’s “Batman;” and so many more.

Seemingly retired, his storied acting career appears to have ended. Nicholson, who turned 87 in 2024, hasn’t appeared onscreen since 2010’s “How Do You Know.” Since then, he’s become a reclusive figure, rarely seen out in public for years until re-emerging in 2023 to take his familiar courtside seat to watch his beloved L.A. Lakers play.

An elusive figure in recent years, his impeccable Hollywood resume has occasionally been overshadowed by controversies in his personal life. To find out more about that side of his life, read on for a deep dive into the shady side of Jack Nicholson.

If there’s a through-line that connects Jack Nicholson’s most memorable movie roles, it’s the anti-authority streak displayed by his characters, evident in films such as “One Flew Over the Cuckoo’s Nest,” “Five Easy Pieces,” and “Chinatown.” Not surprisingly, that was also a trait that Nicholson demonstrated in real life while growing up in Neptune, New Jersey.

“I was always against authority, hated being told anything by my teachers, by parents, by anyone,” he explained in a 1993 interview with The Independent, revealing that he became somewhat legendary with his teachers. “At school, I created a record by being in detention every day for a whole year … I don’t like listening to what other people think.”

As it happened, that particular element of Nicholson’s character did not diminish over time. That was evident in Nicholson’s 2007 interview with Esquire, where he declared, “I hate advice unless I’m giving it.” He added, “I hate giving advice, because people won’t take it.”

During his heyday as a Hollywood star during the sexually liberated 1970s, Jack Nicholson developed a well-earned reputation as one of Tinseltown’s most notorious lotharios. When The Independent put together a list of the all-time great seducers, Nicholson’s name appeared alongside Casanova and NBA great Wilt Chamberlain, who famously boasted of bedding 20,000-plus women.

While Nicholson has long been rumored to have slept with more than 2,000 different women in his day, he’s also admitted that he really had no idea what the actual number is — and didn’t particularly care. “I don’t count,” he told the Daily Mail in 2011, admitting that, as a septuagenarian, those days were behind him. “I can’t hit on women in public anymore,” Nicholson admitted. “I didn’t decide this; it just doesn’t feel right at my age.”

Among those who’ve seen Nicholson in action, so to speak, is “Baywatch” alum Pamela Anderson. In her memoir, “Love, Pamela,” Anderson recalled entering a bathroom in the Playboy Mansion, only to find herself intruding upon Nicholson getting intimate with two women. “I walked by to use the mirror, bending over the sink to fix my lip gloss,” Anderson wrote, via an excerpt appearing in Variety. “Trying not to look, but I couldn’t help myself and caught his eye in the reflection. I guess that got him to the finish line, because he made a funny noise, smiled, and said, ‘Thanks, dear.'”

There’s no denying that Jack Nicholson has made some controversial remarks in his day. For example, during a 1994 interview with Vanity Fair, he rakishly quipped, “You only lie to two people in your life: your girlfriend and the police. Everybody else you tell the truth to.”

However, one of his former paramours has claimed that Nicholson once told her something far more shocking than that. “The only time I ever disagreed with him was when he said that I had to admire Hitler for his determination, as Hitler had held to his beliefs,” wrote Susanna More in her memoir, “Miss Aluminum,” as excerpted in The Sunday Times.

More, who claimed to have had a brief affair with Nicholson in the 1970s while she worked as a script reader, insisted that she was stunned and angered by his admission. “I was furious,” she recalled, but didn’t want to push back. “I was afraid to argue with him, fearful that it would cause me to think less of him,” she added. “As gentle and as malleable as he then was with women, he had a certain fondness for tyrants.”

Jack Nicholson co-starred with comedy superstar Adam Sandler in the 2003 comedy “Anger Management,” portraying an anger management counselor with his own severe issues with anger. There was no scarcity of irony when he took that role, given that a few years earlier, Nicholson had been involved in a headline-making road rage incident that saw him explode in violent rage.

While driving to a golf course in 1994, Nicholson was cut off by another motorist. When he pulled up next to the offending driver’s car at a stoplight, Nicholson exited his vehicle, pulled a golf club from the trunk, and proceeded to smash the other car’s windshield to smithereens. (He reportedly paid the driver $500,000 in an out-of-court settlement.) “I was out of my mind,” he later told Golf Digest, revealing he was stressed out from directing a movie while also coping with the recent death of a friend. “I was on my way to the course, and in the midst of this madness I somehow knew what I was doing,” he added, “because I reached into my trunk and specifically selected a club I never used on the course: my 2-iron.”

Speaking with The Sun, Nicholson confirmed his temper sometimes got the best of him. “Anger has always been a problem and every once in a while I just have to let it out,” he explained. “I always regret it later.”

Jack Nicholson’s hot temper was at the heart of an alleged 1996 assault. The New York Daily News reported that a woman claimed Nicholson violently attacked her while she attended a dinner party at her home. According to her complaint, she’d criticized him for attempting to kick former girlfriend Susan Anspach out of a house he owned, and an argument ensued. She claimed that Nicholson shoved her in the chest so hard that one of her silicone breast implants ruptured. According to the Daily News, she demanded Nicholson pay her a $10 million settlement; when he refused, she shopped her story to the National Enquirer, demanding $100,000; the tabloid reportedly took a pass.

That wasn’t the only time Nicholson was accused of getting violent with a woman. In a 2000 lawsuit filed by sex worker Catherine Sheehan, she claimed she and a friend had been hired by Nicholson. Things became fraught, however, when she tried to collect the agreed-upon $1,000 fee.  The Associated Press reported (via CBS News) that “Nicholson became loud and abusive,” the suit stated, “demanding to know what plaintiff was talking about, stating that he had never paid anyone for sex as he could get anyone he wanted as a sexual partner.” Sheehan claimed that Nicholson pulled her hair and smashed her head on the floor and subsequently paid her $32,500 as a settlement. She sought further damages and to have the original settlement rescinded.