Hugh Hefner

Kendra Wilkinson, Hugh Hefner, and Hank Baskett at the Playboy Mansion last weekend

When your current husband meets your 89-year-old ex-boyfriend #justkendrawilkinsonthings


Holly Madison and Hugh Hefner in 2007

No one's talking about Holly Madison anymore -- nor should they be -- so hey, perfect time for a tell-all book, right? It's titled Down the Rabbit Hole: Curious Adventures and Cautionary Tales of a Former Playboy Bunny and absolutely no one's gonna buy it. Via Us Weekly:
When she finally had had enough and decided to move out, the Playboy Enterprises founder tried one last tactic to get her to stay -- putting her in his will.

"It was there, in black and white," she wrote. "The will stated that $3,000,000 would be bestowed to Holly Madison at the time of his death (provided I still lived in the Mansion). At the time, it was more money than I'd ever know what to do with... But I didn't want it. I actually pitied him for stooping to that level. I couldn't help but be offended. Did he really think he could buy me? I put the folder back on the bed just as I had found it and never breathed a word of it."
The girl fucking the old rich pervert for fame was offended that he had the nerve to write her into his will. Sounds right -- I'd be offended if I was her, too. Hugh Hefner is gonna live to be 150. Holly needed that money right away to buy mutual funds. Or bigger tits. Definitely one of those two.

*5 Holly Madison pictures total in the gallery:

  • Holly Madison Claims 1
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Crystal Harris and Hugh Hefner at the 2013 Playboy Playmate of the Year announcement at The Playboy Mansion in Beverly Hills (5/9)

Crystal Harris says she doesn't even notice the 60-year age difference between her and "husband" Hugh Hefner. Oh yes, of course. I'm sure it's just like a normal marriage, minus the whole making sure his oxygen tank is hooked up when she blows him. She told Access Hollywood Live:
"We're happier than ever, things are better now than they were then. Hef loved me more than I've ever felt in my life ... Hef's very romantic, very cosy. We really care about each other and get along great. I don't notice the age difference. Hef's a lot of fun."
Oh yeah, Crystal doesn't notice the age difference at all, especially when Hugh's day nurse is picking gold-digger pubes out of the old man's dentures. Should we pretend that Crystal isn't completely disgusted by Hugh and his wrinkled balls? I guess her gag reflex is nullified by Hef's multimillion dollar fortune -- it's just a matter of getting the old coot to keel over while he's inside of her. With any luck, Hef's middle-aged kids will soon have him declared mentally incompetent so they can access his checking account, so all of Crystal's hard work (e.g. being a portable toilet for a man with no bowel control) will be for naught. Only time will tell, but rest assured that the clock is ticking . . . tick . . . tock . . .

*15 Crystal Harris and Hugh Hefner pictures total in the gallery:

  • Crystal Harris Age Difference 1
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Hugh Hefner and his entourage at Disneyland in Anaheim (9/5)

Wanted to get these pics of Hugh Hefner up as soon as possible because he could literally die at any second, and then I'd just seem like a callous shithead. Speaking of shit, will someone please change Hugh's diaper? The Jungle Cruise was much scarier than anticipated.

*25 Hugh Hefner pictures total in the gallery:

  • Hugh Hefner Deaths Door
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Crystal Harris at the grand opening of Sapphire Pool & Day Club in Las Vegas (5/4)

Crystal Harris managed to convince her husband Hugh Hefner to buy her a $5 million house in the Hollywood Hills. Wait, doesn't that count as elder abuse? From TMZ:
Hugh Hefner really loves his 27-year-old Playmate wife Crystal Harris. We're told he's created an intricate plan to set her up in a multi-million dollar estate, where no one in his world can displace her once he dies, but there is one hitch. Hef plunked down $5 million last month for a 5,900-square-foot Hollywood Hills mansion, which is held in trust for the 2 of them.  Short story -- Crystal owns the house with him.

Playboy sources tell us the couple is happily living at the Playboy Mansion, and they have no plans to move.  So why, you ask, did they buy the Hollywood Hills home?  Fact is Hef is a renter!  He doesn't own the Playboy Mansion -- it's owned by Playboy Enterprises. We're told the 87-year-old perennial player wants to make sure Crystal has a roof over her head when he's gone, and the Hollywood Hills estate fits the bill.
Maybe it's time for the handlers to go ahead and put Hugh in a retirement home, because he's clearly lost his mind. I know some of you are poor and can't afford SiriusXM, so allow me to remind you what a-then-single Crystal Harris told Howard Stern about the man she is now madly in love with:
Harris made faces of disgust as she divulged details of her intimate life with the original Playboy, admitting that the pair only engaged in intercourse once and when they did, it was only for "two seconds."  "I'm not turned on by Hef, sorry," she said, laughing. (HuffPo)
Instead of a house, Hugh might want to invest in some guy friends that can steer him clear of the gold diggers at the end of his sad life. Perhaps a wingman for hire. Of course, I'm your huckleberry assuming the price is right, Hugh. For a measly six figures, I'll keep those skanks away and make sure you end up with a girl more suited for your needs: a wet nurse who's willing to change colostomy bags.

*10 Crystal Harris pictures total in the gallery:

  • Crystal Harris New House 1
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The least sluttiest picture I could find of Crystal Harris

Crystal Harris and her new husband Hugh Hefner actually want kids. Yes, that Hugh Hefner. The one who was born two years before bubble gum was invented in 1928. In unrelated news, Viagra stock just shot up 800%. From UK tabloid The Daily Star:
At the grand old age of 86 Hugh Hefner still wants to impregnate woman. Well, one woman to be precise - his 26-year-old new bride Crystal Harris. Despite their 60-year age gap, Hugh married British model Crystal in a small ceremony at the Playboy Mansion in Hollywood on New Year's Eve. And now the Playboy mogul, estimated to be worth $80 million, told friends he wants to become a father one last time.

Our LA insider revealed: "Crystal's desperate to have Hugh's baby. She thinks it would be the most beautiful way imaginable to show him how much she really loves him. Hef is insisting he's still man enough for the job, telling family and friends at the wedding he's still up for it. He wants to show the world that age shouldn't stop you doing anything."
Hey guys, do you feel that? Those aren't ants tickling your neck and back -- what you're feeling is your skin crawling from the image of old man Hef whipping out his wrinkly beef jerky stick much to the horror of his gold-digging baby momma in training. There's not enough Viagra and tranny porn in the world that'll get Hef's waterlogged linguini dick hard enough to mush into the loosest of skanky Playboy pussy, let alone deliver a viable load into it. Maybe Crystal should swab a load off the floor during the next Mansion orgy and fill a turkey baster with it -- it's not as if Hugh will even be around to raise the lil' money shot. Enjoy your lunch, friends.

*10 Crystal Harris pictures total in the gallery:

  • Crystal Harris Hugh Hefner Kids 1
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Hugh Hefner's ex Crystal Harris is a total bitch

You don't kick a man's oxygen tank when he's down. I'm sorry but you just don't. The nerve of this Crystal Harris bitch. From the New York Post:
Crystal Harris, 25, told radio shock jock Howard Stern on Tuesday that she had never seen the 85 year-old magazine mogul naked, and that their sex life left a lot to be desired.

"Hef doesn't really take off his clothes. I have never seen him naked," she giggled in an appearance on Stern's SiriusXM radio show . . . "I was over it. I just like, walked away. I am not turned on by Hef. Sorry."

Harris, who left Hefner and his Playboy Mansion five days before their planned June 18 wedding, claimed the pair only had sex once during their two-year relationship, and that it lasted "like about two seconds."
I don't know who comes across worse in this story -- the 85-year-old grandfather that lasts only 2 seconds in the sack or the gold-digging prostitute who actually had sex with the 85-year-old grandfather that lasts only 2 seconds in the sack. In Hugh's defense, I probably wouldn't have lasted much longer if I nailed someone that had tits like Crystal. And in Crystal's defense, the smell of hundred dollar bills can cover the stench of Ben Gay and Musilex.

*37 Crystal Harris pictures total in the gallery:

  • Crystal Harris Total Bitch 1
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Hugh Hefner and Anna Sophia Berglund at the 6th Annual Kandyland Party at the Playboy Mansion in Beverly Hills (6/25)

After being unceremoniously dumped by that bitch Crystal Harris, Hugh Hefner already has a new girlfriend. I knew this tale would have a happy ending! People says:
Meet Anna Sophia Berglund: the Playboy founder's latest lady.

"With Crystal gone, Anna is my best girl," Hefner, 85, Tweeted. "Anna is really one in a million."

Berglund is no stranger to the mansion. She was the magazine's Playmate of the Month for January 2011, and has made appearances on The Girls Next Door and Holly's World.
You want to know the creepiest thing about this relationship? Hugh first started collecting Social Security benefits when Anna was three-years-old. Three. All together now: ewwwwwwwwwwwwwww

Since this story is worthless without NSFW pics of Anna, click here, here, here, and here

*14 Anna Sophia Berglund pictures total in the gallery:

  • Anna Sophia Berglund Hefner Girlfriend 1
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Make way for Hugh Hefner!

Hugh Hefner is officially old. He was spotted riding a motorized scooter Thursday at Disneyland. Did you know that Hugh was 29(!) when Disneyland officially opened in 1955? I shit you not. It cost $1 -- ONE DOLLAR -- to get in. He's so old that when it opened, his fiancée Crystal's mom wasn't even born yet.

I dare you to read a creepier post than this all week.

*10 Hugh Hefner pictures total in the gallery:

  • Hugh Hefner Rascal 1
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Hugh Hefner and Crystal Harris

When you have articles of clothing older than your fiancée, that's a pretty big clue that you need a prenup. Nevertheless, TMZ says:
He's 84 and worth $43 million ... she's 24 and knows he's worth $43 million -- yet sources close to Hugh Hefner and Crystal Harris tell TMZ neither has uttered those dreaded words ... "prenuptial agreement."

Hef's third wedding is just 10 weeks away, but we're told he hasn't raised a prenup convo because he "actually cares" about Crystal and doesn't want to ask her to sign one. We're told Crystal doesn't think Hef will bring it up before they tie the knot.
Of course Hef doesn't need a prenup. Dude is 84. Even if Crystal divorces him in a year and takes half his fortune, he won't remember it. The only thing 84-year-old men care about is applesauce, not if they'll have enough money to live on in ten years.

*5 Hugh Hefner pictures total in the gallery:

  • Hugh Hefner No Prenup 1
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