Hugh Hefner’s Gonna Die Alone

June 14th, 2011 // 58 Comments

A few months ago, Crystal Harris was rumored to be banging Dr. Phil’s son behind Hugh Hefner‘s back. Possibly even literally, the man’s insanely old. Fast forward to today where TMZ reports Hef has decided not to make Crystal a permanent employee at the Playboy Mansion. Or “his wife” as he’s been known to call it over soup:

Our sources — who are all at the mansion — say Crystal and Hef had a nasty argument this weekend on the phone. When the dust settled Crystal decided to 86 the nuptials and quickly moved her stuff out.
The wedding was supposed to go down Saturday.

Awesome. Now he can finally marry Holly Madison, and the two of them will grow old and gray together, but only into next week when he croaks and/or can’t stand her blabbering during his stories. “Bah! Why do these contraptions always talk so much? Tulliver, send in the next one! And be quick about it, I’m dying.”

Photo: Splash News


  1. cc

    Geez, you can’t even find a faithful golddigger anymore.

    • Honest Abe

      HE IS ALREADY DEAD! They’ve been doing the “Weekend at Bernie’s” thing for the last 5 years!

  2. Clarence Beeks

    the only reason I am surprised is I thought she’d go for the cash. I mean, she’s already fucking him…..

    • Richard McBeef

      sitting on top of a pile of loose skin isn’t really fucking him, but it’s close enough to be disgusting and shameful.

  3. rough

    ALL advanced cleaning power is still not as powerful as good ole Clorox? Who’s in charge of logistics at the playboy mansion?

    The man has an image to keep!

  4. rough

    Hey I just did a free commercial for clorox.

  5. Deacon Jones

    I wonder what she did after the first time she blew him.

    Rocked back and forth on toilet while she quickly snorted Oxys?

  6. Michelle

    Going to die alone??? Has this man ever been without a woman? Something tells me being alone is the least of his worries.

  7. “When the dust settled”… so, Hef sat down?

  8. Russ Collins WSJ

    He is gonna die with my cock in his mouth.

  9. Rancid

    I could already tell you this woman is as stupid as a box of rocks. She can’t even wait for the ten minutes it would take for this guy to croak? Seriously, all she would have to do is sit down, check her watch every so often, and BAM she’s suddenly a fucking billionaire.

    • Kelley

      Yeah, no shit … he’s already 85 years old. She’s been trying to convince everyone she’s 24, too. Nice fake wonk-tits … real tits are not square at the sides … a fact that seems to be lost on Kim Kardashian (and Katy Perry) …

    • vitobonespur

      Can anyone say “prenuptial agreement”?

  10. Mr Obvious

    He had a good life.

  11. awe i feel bad for the old bugger, we should pitch in and send him some pussy flavored pablum or something

  12. me


  13. AleisterCrowley

    Each dude she dates is worse than the last. Next up: Gary Bucey!

  14. AtomicMug


    This time, I really thought Crystal Harris was “the one”.

    I can’t figure out why Hef is such an icon.

    He’s a one-foot-in-the-grave billionaire, and he keeps getting dumped — by gold-diggers.

    Basically, prostitutes are the only women this guy can get. What a tool.

  15. dee cee

    His mansion is a stinky, germ-riddled, decaying, nasty place to live and being a dirty, grumpy, old rotting corpse, Hef’s the worst of her nightmare to endure, for sure.. She’s better off waiting tables than to suffer another moment as a sex slave to this rude jerk. I imagine his loyal staff, grown children will get the most of any inheritance, and she would probably gain a few million for the bother.

  16. “Hey you kids, get off my lawn!”

  17. Mandy

    I know I sound crazy, but I loved the Girls Next Door show and I actually thought Hugh and Holly were a good couple. Obviously Kendra and Bridget were there for money/fame, but Holly actually seemed to love him. Who knows, it’s a reality show, it’s all fake. But I always got the feeling that their relationship was real.

  18. Why is there a picture of him with Gwyneth Paltrow?

  19. cherrypie

    What would Dr. Phil say ???

  20. I totally believe SHE decided to “86 the nuptials”…It’s not like she’s bringing something UNIQUE to the table, I thought she WAS Bridget until I read the caption. She’s a generic bleach blond fake boob bimbo…what a truly unique skillset.

  21. RoboZombie

    Justin Timberlake looks horrible here!

  22. HEF


  23. i thought he was already dead

  24. JohnQPublic

    buncha haters… this man is a legend.

  25. Linxx

    smart man. this man is a genius

  26. Hank

    When he dies, they need to put him on the $100 bill, and name one major airport, several freeways, and at least 100 high schools after him.

  27. lol

    he probably finally let her see the prenup and she didn;t think it was what she though it would be. i can see him stringing these dumb girls along…

  28. lol

    she isnt 25, all lies. she’s in her 30′s.

    shows just how in love and loyal she was, it wasnt enough money, she ran. she thinks it makes her look like she isnt a golddigger… just the opposite. and he’s sleazy for persuading her she’d be taken care of.

  29. Spencer’s really let himself go.

  30. Hugh Hefner Crystal Harris Wedding Cancelled
    Commented on this photo:

    Good for her! She can do so much better than that old windbag coot.

  31. Basil Pemberton, Esq.

    That refreshing young lady is no unattached?.
    My heart soars as if Cupid’s own arrow has struck me !

  32. Dr Ha-Ha

    I’m not a Hef hater, but this man’s dream turned into a nightmare a long time ago, and one suspects the only reason he doesn’t seem to realise it, is because he’s never fully emotionally grown up.

  33. Merrilyloulabelle

    Now this tramp will be Dr Phil’s problem! His other son already married a Playboy bunny I think. The boys’ love them some bunnies.

  34. DKNY

    She probably decided to “86 the nuptials” because the dude is fucking 86!

  35. Brooke

    I saw it mentioned on another gossip site that today she released a single. Had no idea she was a “musician”. Her single is released the day the media reports her break-up with Grampa Hugh!? Gee, what an amazing coincidence…. you’d almost think this whole thing was orchestrated to drum up attention and she’ll be back to coughing up gray pubic hairballs once her “song” fails to bring in a dime.

  36. If by “alone” you mean “of a heart attack caused by banging triplet skanks”, then yes.

  37. “I haven’t felt this betrayed since the civil war”, quipped Hef.

  38. major

    banging around with dr phil jr will prove to be pretty expensive in the long run. cant wait for her bankruptcy story in 10 years…

  39. Joelseph

    Whaaaaaat?!? I cant believe people visiting a website like this would be so angry against Hef. The respect for this guy should be multi-level.

  40. the captain

    you really think this is bothering him……………

  41. Jean

    Doesn’t Hef realise he is old and ugly? I whould get sick at the sight of him. Marry him? Gross!

  42. Hugh Hefner Crystal Harris Wedding Cancelled
    319-T. Sewell
    Commented on this photo:

    Without that old dumbass guy, she can do hell a lot better.

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