Jack Nicholson and Lara Flynn Boyle, 33-Year Age Difference

Jack Nicholson and Lara Flynn Boyle

Jack Nicholson and Lara Flynn BoyleJack 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.