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Jack Nicholson: The complete hookup history

By / 04.26.12



Last week we took a look at one of the most prolific celebrity womanizers in Leonardo DiCaprio. This week we continue our series with a man who has allegedly hooked up with at least as many famous women as Leo: Jack Nicholson. Of course the difference here is that Jack just turned 75 on Sunday while Leo is half that age. That being said, it’s still a rather impressive list. Jack also gets points for scoring with women many, many years younger than him (noted below).

NOTE: In the interest of brevity, we’ll just list all his ladies up to his longest romance: Anjelica Huston. It’s also been reported that Jack has nailed over 2,000 women, but today we’re just going to focus on the famous ones.

Previous hookup histories on Guyism.

Pre-Anjelica

Sandra Knight (1958-1968), Mimi Machu (1967-1971), Susan Anspach (1969-1971), Rita Moreno (1970), Candice Bergen (1971), Michelle Phillips (1971-1972).

Anjelica Huston (1973-1989)

Jack and Anjelica were an item for 16 years, but as you will see as you scroll down, it wasn’t always exclusive. Broke up permanently when knocked up another woman.

Barbara Allen & Jill St. John (1977)

Neither of these women were with Jack very long, especially since Allen said she was with him for “a little more than a nanosecond.”

Margaret Trudeau (1978)

Yes, this is the former Canadian First Lady, the wife of Prime Minister Pierre Trudeau, and yes this is while she was married to him. Beat that, Leo. (Age difference: 12 years.)

Bebe Buell, Janice Dickinson & Christina Onassis (1980)

Buell and Dickinson were big time models at the time (Jack likes models), and yes, Christina was the daughter of Aristotle Onassis, Jackie Kennedy’s husband. (Age differences: 17, 18, and 13 years respectively.)

Winnie Hollman (1980-1982)

(Pictured on the right.) Despite being a famous model there is very little information or photography of her available on the Web. Still Jack nailed her and we know this because she had one of his kids.

Rachel Ward (1981)

Jack’s first foray into England (he also likes British-born women) was with this actress who spent most of her career in America and Australia and is best known here for her role on The Thorn Birds. (Age difference: 21 years.)

Karen Mayo-Chandler (1987-1988)

His second dip into Britain, this relationship with actress/model Karen Mayo-Chandler lasted about a year as she chronicled to Playboy in December 1989. (Age difference: 27 years.)

Marie Helvin (1988)

Back to America with yet another famous model. Told you he liked models. (Age difference: 16 years.)

Rebecca Broussard (1989-1993)

The woman who was the final nail in the coffin for Jack and Anjelica’s relationship. Jack and Rebecca were never married but he did have two offspring with her. (Age difference: 26 years.)

Tracy Richman (1990-1991)

An American actress (sort of) who very little is information available about on the Internet other than she was in the Charlie Sheen E! True Hollywood Story in 2010.

Amber Smith & Angie Everhart (1993)

This was Jack at the height of his powers. Two of the sexiest models ever. (Age differences: 34 and 33 years respectively.)

Amanda De Cadenet (1995)

Back to England with actress Amanda De Cadenet (now a successful photographer with a show on Lifetime), and ex-wife of both Duran Duran bassist John Taylor and Strokes’ guitarist Nick Valensi. (Age difference: 36 years.)

Lara Flynn Boyle (1999-2001)

This was back when LFB was super hot and about to appear in Men in Black 2. It’s been all downhill from there for her unfortunately. (Age difference: 33 years.)

Kate Moss (2004)

Last trip to Britain for Jack, last famous model for Jack. After this he’s (probably wisely) stuck to less famous women. (Age difference: 37 years.)

Pat Cleveland, Heidi Fleiss & Kelly LeBrock (Dates Unclear)

Two models and a hooker that we’re pretty sure he banged, just not exactly sure when.

Other less-substantiated alleged flings…

Julie Delpy, Sabrina Guinness, Marg Helgenberger, Joni Mitchell, Zouzou



Photo credit: YouTube/Warner Bros.


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Douglas Charles
About Douglas Charles... Douglas Charles is the co-founder of Guyism.com, now a part of BroBible. His experience includes operating an assortment sports and entertainment Web sites over the past decade, but his specialty is discovering sexy women from all over the world that he knows he will never have a chance with, let alone meet - a quality he shares with 99.99% of his readers.

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