Jack Nicholson first started in Hollywood working as a gofer at the MGM cartoon studio. When he was offered a junior level position as an animation artist, he decided it was time to try his hand at his real passion: acting. His first role was in the 1958 thriller The Cry Baby Killer, which led to several other acting jobs, although none of them really generated much interest with mainstream moviegoers.

That changed when Nicholson won the part of a drunken lawyer in the 1969 film Easy Rider—a role that instantly took the actor from B-list celebrity status to Oscar-nominated movie stardom. The following year, Nicholson landed another Oscar nod, this time for Best Actor in the film Five Easy Pieces. From that moment on, his career in acting was set in motion. Nicholson still holds the title of having the most Academy Award nominations among male actors. He’s been nominated 12 times and has won three golden statues: Best Actor in a Leading Role for One Flew Over the Cuckoo’s Nest in 1976, Best Actor in a Supporting Role for Terms of Endearment in 1984, and Best Actor in a Leading Role for As Good As It Gets in 1997.

As Nicholson’s celebrity status rose over the years, so did his reputation of being a playboy, often romancing much younger women. His first and only marriage ended in 1968, after which he dated actress Anjelica Huston on and off for 16 years—she was 14 years younger than him. He then bedded a slew of young women, including an affair with Margaret Trudeau, the ex-wife of former Canadian Prime Minister Pierre Trudeau. She was 11 years younger when they allegedly hooked up in the back of his car.


Nicholson also dated other younger women including models Bebe Buell (16 years younger) and Janice Dickinson (18 years younger), and actress Rachel Ward (14 years younger)—these are just a fraction of the women he’s been with. The actor has reportedly had sex with over 2,000 women.

One of his more talked about relationships was with actress Lara Flynn Boyle, mostly because of the scandal surrounding their relationship. When they first appeared in public together as a couple in 1999, he was 62 and she was only 29—but their age difference wasn’t the only thing making headlines. Nicholson was reportedly cheating on his long-term girlfriend at the time, 36-year-old actress Rebecca Broussard, and would often leave her and their two children at home to spend the night with Boyle. When Boyle pulled the plug on their affair after a year, Nicholson was said to be heartbroken. But that didn’t stop him from jumping right back into the dating pool.

Nicholson has calmed down in recent years and has even acknowledged that his age may have finally caught up with him. “I can’t hit on women in public any more, I didn’t decide this; it just doesn’t feel right at my age,” he told the Daily Mail. “There were points in my life where I felt oddly irresistible to women. I’m not in that state now and that makes me sad.”

Despite having slept with possibly thousands of women—including much younger women—Nicholson still doesn’t think he’s been successful in navigating through his relationships, partly because he’s never been able to shake his playboy reputation. “I’ve been so struck I’ve said, ‘Come on, let’s go, let’s get married.’ But no woman has ever recognized what I say as being legitimate,” says the actor. “Now I think I have a gap I won’t ever cross.”

A good place to start might be to find someone his own age, since dating younger women hasn’t really worked in his favor.


What do you think: Now in his mid-seventies, will Jack Nicholson ever be able to shed his past and find real love, or has his playboy reputation as “Jack the Jumper” ruined whatever chances he has left?

Gannon, L., “‘I used to feel irresistible to women. Not any more’: The melancholy confessions of Jack Nicholson,” Daily Mail web site; http://goo.gl/jugyk, last accessed July 5, 2013.

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