Jack Nicholson was notorious for being a ladies’ man even in his sixties. A Hollywood superstar since he broke through with Easy Rider in 1969, by the late 90s Nicholson had romanced more high-profile women than anyone could count – and he was about to embark on one last great love affair.

From 1999 to 2004, Nicholson and actress Lara Flynn Boyle had an on-off relationship that was eventful from the start. Undeterred by their 33-year age gap, when Nicholson first met the then-29-year-old Boyle, he asked her out on the spot – despite the fact that her boyfriend of the time, David Spade, was right next to her.

Twilight of the lothario

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As renowned as he is for being one the best actors of his generation, Jack Nicholson is almost equally notorious for his ways as a lothario. Only married once – to actress Sandra Knight, from 1962 to 1968 – Nicholson has enjoyed the company of untold numbers of women over the years; according to Nicholson himself, the number could be as high as 2,000.

While never the most conventionally handsome of men, Nicholson’s confidence and charm frequently cast a spell over the opposite sex. This was true of some of his co-stars, including Diane Keaton, who admitted having had “the biggest crush on [Nicholson] for 20 years” when they co-starred in 2003’s Somethings Gotta Give.

While Nicholson’s many conquests include actresses, models and other prominent figures, one of his few long-term partners was Anjelica Huston, with whom he had an on-off romance between 1973 and 1990. Huston was only 21 when they first met, whilst Nicholson was 36. By the late 90s, however, Nicholson was approaching 60 years old, and was beginning to question the age gaps between himself and some of his beaus.

In a 1997 interview, Nicholson admitted to having misgivings about playing the on-screen love interest of the much younger Helen Hunt in As Good As It Gets. (“The obligatory [younger] love interest for the middle-aged leading man is a cliché of the movies that I don’t like as a member of the audience and am always a little offended by”.)

Then, in June 1999, any sense that Nicholson (by then aged 62) was no longer interested in younger women was temporarily dismissed when he crossed paths with 29-year-old actress Lara Flynn Boyle.

“He’s worse than Trump!”

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Born in Davenport, Iowa on March 24, 1970, Lara Flynn Boyle found her breakthrough role as Donna Hayward in TV’s Twin Peaks. She dated her Twin Peaks co-star Kyle MacLachlan for two years, before seeing John Patrick Dee III, whom she married in 1996.

By 1998, Boyle and Dee divorced, and not long after that she began dating the actor and comedian David Spade, who had once worked with Nicholson when the actor made a guest appearance on Saturday Night Live. In June 1999, Boyle and Spade attended a launch party for Austin Powers: The Spy Who S****ed Me. Here, they were approached by Nicholson, who Spade says swept in and started flirting with Boyle immediately.

“Nicholson asked Lara Flynn Boyle out in front of me, while we were all smoking a doob somewhere,” Spade recalled. After Nicholson left, Boyle reportedly criticised Spade for not asserting their relationship, while insisting she had no interest in the much older actor.

“I said, ‘I’ve been in this town long enough to know when I’m outranked,'” Spade has remembered. “‘You’re either gonna go out with him or you’re not.’ She goes, ‘No way. He’s worse than Trump!'” Spade claims that he thought nothing more of it, and that he and Boyle continued to date each other.

Just one month later, Spade received a phone call from the National Enquirer and learned that Boyle and Nicholson had been caught up in a car crash during a secret tryst. This promptly ended that relationship and marked the beginning of the media’s fascination with Nicholson’s latest fling.

“A good-time young lady”

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After the tabloid revelation about the traffic collision (in which Nicholson had been driving Boyle’s mother’s Mercedes), Nicholson and Boyle went public with their relationship. They shunned interviews and avoided questions about their romance, but were soon living together, and were seen at numerous events including the Oscars, the Emmys, boxing matches and basketball games.

Nicholson and Boyle even attended a White House dinner party hosted by the Clintons. Describing herself as a “bad girl”, Boyle later confessed to stealing a toothbrush holder from the White House and concealing it in her evening bag.

Reactions of those close to the couple were mixed. Nicholson’s biographer Patrick McGilligan called Boyle “a good-time young lady who liked to party as much as Jack, smart and sassy.” Producer Harry Gittes, a mutual friend of Nicholson and Boyle, cryptically remarked, “Jack and Lara Flynn Boyle are very interesting together, and I love her, but she’s a handful.”

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Tabloid interest flared once again in September 2000 when Boyle abruptly moved out of Nicholson’s house just over a year after their relationship had officially begun, leading to speculation of a split. News agency WENN approached Boyle at the 2000 Emmy Awards and asked her where Jack was, to which she reportedly replied with sarcasm, “Where isn’t he?”

Salon Magazine reported that Boyle was later overheard saying, “I have to find a man, a good man.” However, Boyle assured Talk Magazine that she and Nicholson were still an item. “I’m in love with love,” she noted. “I mean, you hit a certain point when why would you spend a certain amount of time with somebody if you weren’t?”

“Jack is solo, solo, solo”

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By late 2000, Nicholson and Boyle were often spotted out in public together again (including at the wedding of Michael Douglas and Catherine Zeta-Jones). Speculation was rife about the unorthodox, on-off nature of their relationship, but as another of Nicholson’s previous girlfriends Karen Mayo-Chandler explained in a 2002 interview, Nicholson could be very particular about such things.

Mayo-Chandler (who had remained friends with Nicholson after they dated) remarked that the actor “preferred sleeping alone and he didn’t like to have anyone staying over at his house any more. He would send his girlfriends home afterwards. That never happened when I was with him.”

In January 2001, Boyle gave a rare interview about her relationship, admitting that she could never imagine settling down with Nicholson. “Jack is solo, solo, solo. It’s a learning experience, being around him.” She then added, “He can stimulate me mentally, too, you know.”

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Nicholson and Boyle were spotted together at the Moscow International Film Festival as well as at the Wimbledon Championships in the summer of 2001. However, in January 2002 – soon after she had completed work on what would be her last major movie, Men in Black II – Boyle gave further details of the romance, suggesting that they were taking a break.

“It’s hour to hour with me,” Boyle said of her relationship status, amid rumours she’d started dating Eric Dane instead. “I hate to give you an answer because by the time you put it in print it is so something else… I don’t have any deadline with Jack. Right now I’m by myself.”

“Jack’s not the party-loving womaniser he used to be”

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Even towards the end of their relationship, Boyle was full of praise for Nicholson. “Jack is a real man,” she said. “People are fascinated by Jack. I understand that. I’m fascinated by him, too. It takes a confident man to be attracted to someone like me.”

Nicholson and Boyle officially separated for good in 2003. One friend commented, “Jack was more into the relationship than she was and after a year together she wants to date other people.” Boyle went on to see actor Eric Dane and businessman Jay Penske, although neither relationship lasted long.

Nicholson, meanwhile, made headlines in 2004 after he was spotted with supermodel Kate Moss, and at the premiere of 2006’s The Departed, his date was actress Paz de la Huerta – but if relationships ensued, they would not appear to have lasted long. An unnamed party close to Nicholson remarked in 2017, “Jack’s not the party-loving womaniser he used to be. He just prefers a select few in his inner sanctum now.”

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After their split, Jay Penske described Boyle to the press as too “high maintenance,” and Boyle herself has confirmed such criticisms. “I am a handful,” she told one journalist. “I am a drama queen, and yes, I am very high-maintenance. I am very opinionated, I have a lot to say and I am confident. God bless you if you want to date me. Good luck – you’re going to need it.”

Boyle went on to marry real estate investor Donald Ray Thomas II in 2006. She doesn’t have any children. After a five-year absence from show business, she returned to filmmaking with Death in Texas (2020), but has made few appearances since then.

“I would love that one last romance”

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Jack Nicholson, meanwhile, has six children from five past relationships. He is reportedly single, and remains close friends with Hollywood stars like Danny DeVito and Joe Pesci. He made his last acting appearance in 2010’s How Do You Know, and is now considered retired.

In 2013, in what is to date one of his last interviews, the then-75-year-old Nicholson reflected: “There were points in my life when I felt oddly irresistible to women. I’m not in that state now, which makes me sad… I would love that one last romance, a real romance, but I’m not very realistic about it happening.”

This wasn’t enough to keep the old devil from boldly approaching and flirting with a mid-interview Jennifer Lawrence at the 2013 Oscars.