Hugh Henfer is the envy of millions of men around the world. Despite not being close to a spring chicken, the Playboy founder has a...

by Tyler Johnson at

Legendary Playboy founder Hugh Hefner turned 88 yesterday and he celebrated as only Hef can: with his signature mix of old-fashioned class and inappropriately aged half-naked women.

Hugh Hefner and Crystal Harris Tweet

Crystal Harris dumped Hefner in brutal fashion in 2011, but nearly three years later Crystal and Hugh are happily married and she reportedly helped organize his b-day soiree held earlier this week.

"Tonight we start my weekend birthday celebration with the screening of my all-time favotire film 'Casablanca,'" Hef tweeted just before the event.

It's gotta be something of a letdown to be invited to the Playboy Mansion only to find out you're gonna be watching a 70-year-old movie, but in the style befitting Hef, there were plenty of lovely ladies in attendance, with a reported 28 current and former Bunnies on hand.

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by Tyler Johnson at

With news that Johnny Depp may have gotten Amber Heard pregnant, celebrity couples with huge age differences have been a popular topic of discussion today. 

We thought we'd remind you of some of Hollywood's most noteworthy May-December romances, because let's face it - some of these guys are so old they probably forget about their own relationships.

13 Stars With Big Age Differences
Brad is 12 years older than Angie. One of many Hollywood couples with a giant age gap.
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Brad Pitt and Angelina Jolie - 12 Years

1. Brad Pitt and Angelina Jolie - 12 Years

Brad is 12 years older than Angie. One of many Hollywood couples with a giant age gap.


Johnny Depp and Amber Heard - 23 Years

2. Johnny Depp and Amber Heard - 23 Years

Yes, Amber and Johnny are separated by 22 years. One of many Hollywood couples with a giant age gap.


Aaron Johnson and Sam Taylor-Wood - 24 Years

3. Aaron Johnson and Sam Taylor-Wood - 24 Years

Sam is 24 years older than actor Aaron! One of many Hollywood couples with a giant age gap.


Jennifer Lopez and Casper Smart - 17 Years

4. Jennifer Lopez and Casper Smart - 17 Years

Jen is 17 years older than Casper. One of many Hollywood couples with a giant age gap.


Bradley Cooper and Suki Waterhouse - 17 Years

5. Bradley Cooper and Suki Waterhouse - 17 Years

Bradley is 17 years older than Suki. That may be why he's so secretive about their relationship.


Ashton Kutcher and Demi Moore - 15 Years

6. Ashton Kutcher and Demi Moore - 15 Years

Here's a twist: Demi is 15 years older than Ashton. One of many Hollywood couples with a giant age gap.


Matthew McConaughey and Camila Alves - 14 Years

7. Matthew McConaughey and Camila Alves - 14 Years

Matthew is 14 years older than Camila. One of many Hollywood couples with a giant age gap.


Stephen Moyer and Anna Paquin - 13 Years

8. Stephen Moyer and Anna Paquin - 13 Years

Stephen is 13 years older than Anna. One of many Hollywood couples with a giant age gap.


Megan Fox and Brian Austin Green - 13 Years

9. Megan Fox and Brian Austin Green - 13 Years

Brian is 13 years older than Megan. One of many Hollywood couples with a giant age gap.


Beyonce and Jay Z - 12 Years

10. Beyonce and Jay Z - 12 Years

Beyonce and Jay are separated by 12 years. One of many Hollywood couples with a giant age gap.


Michael Douglas and Catherine Zeta-Jones - 25 Years

11. Michael Douglas and Catherine Zeta-Jones - 25 Years

Michael and Catherine recently separated. Maybe their quarter-century age gap had something to do with it.


Harrison Ford and Calista Flockhart - 22 Years

12. Harrison Ford and Calista Flockhart - 22 Years

Ford and Flockhart are separated by 22 years. One of many Hollywood couples with a giant age gap.


Hugh Hefner and Crystal Harris - 60 Years!

13. Hugh Hefner and Crystal Harris - 60 Years!

Hugh is 60 years older than Crystal. These two take the age difference crown!


The winners and probably all-time champions in this category are Crystal Harris and Hugh Hefner who - despite some highly-publicized bumps along the way - didn't let their 60 year age difference prevent them from getting married last year. 

With some couples on our list you may not have realized that the man and woman are from different generations. No one ever talks about the 14 year age difference between Matthew McConaughey and Camila Alves, for example.

And, of course, as it's been since the dawn of time: men get a pass on cradle robbery whereas women get criticized for even the slightest age gap.

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by Hilton Hater at

The man who convinced Kim Kardashian, Pamela Anderson and many others to shed it all in the pages of his magazine has now set his sights on a new beauty.

Speaking to Us Weekly at Playboy's 60th Anniversary at his iconic mansion this week, Hugh Hefner said he has seen Th Wolf of Wall Street and it was "very, very good."

Moreover, Margot Robbie - who plays the wife of Leonardo DiCaprio's main character in the film - is "very, very pretty," according to Hef, who sent along a message to the actress.

"She should be in Playboy! Send her a message! We're ready for her. She would be great."

Six Sizzling Margot Robbie Photos
Margot Robbie is featured here in W Magazine. Hugh Hefner is hoping she poses for his magazine. So are we.
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Margot Robbie in W

1. Margot Robbie in W

Margot Robbie is featured here in W Magazine. Hugh Hefner is hoping she poses for his magazine. So are we.


Margot Robbie Image

2. Margot Robbie Image

Note to movie goers: go see The Wolf of Wall Street. Why? Margot Robbie is in it.


Margot Robbie Photo

3. Margot Robbie Photo

Hello, Margot Robbie! It's not exactly shocking that Hugh Hefner wants this star to pose in Playboy, is it?


Margot Robbie at Wolf of Wall Street Premiere

4. Margot Robbie at Wolf of Wall Street Premiere

Margot Robbie impressed audiences with her role in The Wolf of Wall Street. She's seen here at the UK premiere.


Margot Robbie at the Golden Globes

5. Margot Robbie at the Golden Globes

This is a photo of Margot Robbie at the Golden Globes. We'd like to squeeze her golden globes!


Margot Robbie Pic

6. Margot Robbie Pic

Margot Robbie is hot! She strikes a pose here at the 2014 Critics Choice Awards.


Robbie has been rumored as a mistress of Will Smith, so posing in Playboy would at least change the conversation for this star.

What do you think? Should she do it?

 

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by Hilton Hater at

Kim Kardashian recently re-introduced her body to the public via a sexy swimsuit selfie.

But might we soon be seeing A LOT more of North West's mother?

After making it clear on an episode of Keeping Up with the Kardashians that she's open to taking it all off for Playboy once again, Hugh Hefner has hinted that discussions between Kim and his iconic magazine have taken place.

"@KimKardashian is looking to make it back onto the cover of Playboy, very exciting," Hefner Tweeted yesterday.

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by Hilton Hater at

Julianne Hough donning blackface for Halloween? A bit controversial, we get it.

But as bad as an 87-year putting thoughts into our head of him railing his wife from behind?

Hugh Hefner and Crystal Harris got into the Halloween spirit last night, posting a photo to Instagram of their 2013 costumes:

Miley Cyrus and Robin Thicke from that duo's racy performance at this summer's MTV Video Music Awards.

Hugh Hefner and Crystal Harris Halloween Costumes

Hefner is rocking a black-and-white top akin to the one worn by Thicke during that performance, while Harris holds a foam finger and has her hair in knots. Expect the latter to be a very popular costume across the nation on Thursday night.

Crystal is also Twerking all up on her older husband's crotch, an image that we may never be able to erase from our minds.

This photo makes the controversial routine itself seem tame by comparison. Sort of.

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by Free Britney at

It's Hugh Hefner's birthday on April 9. He is 87 years old!

It's rather amazing that the Playboy founder (who shares Kristen Stewart's birthday) is still going strong after more than half a century in the spotlight.

He's also happily married these days to Crystal Harris.

Old But Still a Playa

Guess even a bachelor who's bedded over 1,000 women has to settle down at some point, and he recently said their union couldn't be more idyllic.

Hey, don't knock it 'til you've tried it. Despite a 60-year-age gap (she turns 27 on April 29), the twosome is basking in wedded bliss and eternally happy.

Wish the man, the myth, the legend all the best below!

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by Hilton Hater at

It may have taken awhile, and it may have included one canceled wedding, but Huge Hefner is now happily married to Crystal Harris.

And the Playboy founder tells the new issue of Esquire that, contrary to popular opinion, his union could not be more ideal.

"All our friends think it's made in heaven," Hefner says. "It's only people who don't know us who simply use us as stereotypes in terms of age and beauty. I just feel very, very fortunate to have found her at this stage in my life. I saved the best till last."

High Hefner in a Tux

And just how many women came before Harris?

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by Free Britney at

Crystal Harris' wedding dress, worn during her New Year's Eve nuptials with Playboy founder Hugh Hefner, is ready to hit the auction block for charity.

"I am auctioning my wedding dress with @charitybuzz to help raise money for lymphoma in memory of Mary," the Playmate tweeted Thursday.

Crystal Harris Wedding Dress

Mary is, of course, Hef's secretary Mary O'Connor, who passed away in January. She was a great friend (and "Mansion Mom") to the girls for 40 years.

According to Crystal Harris, Mary even played a key role in their reconciliation after she went all Runaway Bride on him during their first wedding attempt.

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by Free Britney at

Mary O'Connor, Hugh Hefner's secretary at Playboy for more than 40 years, has died.

"Mary passed away today. We loved her more than words can say," Hef tweeted.

A Smirking Hef

Girls Next Door stars Holly Madison, Kendra Wilkinson-Baskett and Bridget Marquardt all took to Twitter to offer condolences, as did Hef's new wife, Crystal Harris.

Holly wrote, "Rest In Peace Mary."

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by Hilton Hater at

It's official and officially baffling: Crystal Harris married Hugh Hefner for his looks.

Or at least not for his money.

An insider confirms to Us Weekly that Harris signed an "ironclad" prenuptial agreement prior to marrying Hefner last month, a wedding, of course, which took place a year-and-a-half after Harris ended the couple's first engagement.

Crystal Harris in a Sweater

But while Harris will undoubtedly increase her exposure and land more marking deals as a result of marrying the Playboy founder, this tabloid source says Hefner did NOT amend his will to include her.

The senior citizen's fortune is still bound to "his children, the University of Southern California film school and a variety of charities," according to the mole.

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