Shocking Secrets of Young-'n'-Old Celeb Hookups!

Fri., Oct. 10, 2008 12:50 PM PDT by

Hugh Hefner, Kristina Shannon, Karissa Shannon Michael Bezjian / Getty Images

Looks like Hugh Hefner might be doing some early spring cleaning at the Playboy Mansion now that his three blonde babes have become bored bangin' an 82-year-old. Meanwhile, Hef might be ushering in some brand-new girlfriends in the form of 19-year-olds Karissa and Kristina Shannon. As if having a BF almost 58 years your senior isn't absurd enough, you're gonna share him with your sister?

Now, if H2 and the sisters K become an item, how do other May/December H'wood romances throughout history stack up? And enough with the jokes about Demi Moore—she's hardly the worst age offender. Grab your vibrators 'n' Viagra and take a peek:

Demi Moore and Ashton Kutcher: 15-year age difference
A.T. Take: Old enough to be his mom—if she was a really slutty teenager
Projected Number of Nooky Times Per Week: Like Kabbalah-blessed rabbits

Tom Cruise and Katie Holmes: 16-year age difference
A.T. Take: And people say he can't act
Nooky: Excuse me?

Marilyn Manson and Evan Rachel Wood: 18-year age difference
A.T. Take: Gross—not the age gap, just them in general
Nooky: Grosser

Anthony Hopkins and Stella Arroyave: 18-year age difference
A.T. Take: What is it with Oscar-winning old farts getting laid like this?
Nooky: Whenever he wants

John Bryne and Tilda Swinton...and her lover Sondro Kopp: 20- and 17-year age differences
A.T. Take: Kinky—we love it
Nooky: More on one side than the other, take a guess which

Barbara Hershey and Naveen Andrews: 21-year age difference
A.T. Take: Good for her, but did she need to do the younger man and the lips?
Nooky: Lots—but not always with each other.

Harrison Ford and Calista Flockhart: 22-year age difference
A.T. Take: Whatever it takes to get nourishment into this girl is fine by us
Nooky: More often than that girl eats, certainly

Michael Douglas and Catherine Zeta-Jones: 25-year age difference
A.T. Take: Actually, they're the same age, aren't they?
Nooky: With all those cigs Cathy smokes, prolly not much!

Woody Allen and Soon-Yi Previn: 34-year age difference
A.T. Take: Borderline lawbreaker
Nooky: Arresting, literally

Charlie Chaplin and Oona O'Neill: 36-year age difference
A.T. Take: Notorious, even back then
Nooky: Enough to make a silent-movie actress moan

Rubert Murdoch and Wendi Deng: 37-year age difference
A.T. Take: Proof you can buy anything
Nooky: Ew

Frank Sinatra and Mia Farrow: 39-year age difference
A.T. Take: And people say Woody was the only kinky one in his relationship with Farrow, what crap!
Nooky: We'd watch

—Additional sass by Becky Bain

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