Hugh Hefner

Oldest Celebrity Dads
One of nature's little jokes on humanity is that while women's fertility years are limited, men's generally aren't. And since older celebrity guys often have much younger girlfriends and wives, that means lots of famous men become fathers at an age when most men would otherwise b…
Easter in Paris
Perhaps finally accepting the fact that she will never take over the Hilton hotel chain, Paris Hilton slipped on a sparkly Playboy bunny outfit and partied with Hugh Hefner and Snoop Lion for Playboy's annual Easter egg hunt.
Livin' the Dream
If you didn't know better, Hugh Hefner would just be your average geriatric in a nightclub, wearing a captain's hat and falling asleep surrounded by 30 beautiful women. But he isn't. He's Hugh effing Hefner, people, and he's unsurprisingly taken so many women back to Go…
The Good Trophy Wife
Not content with all the tail he was regularly getting in the Playboy Mansion and eager for something deep and real, Hugh Hefner finally tied the knot with generic bimbo Crystal Harris, who was likely eager for bank accounts that were also deep and real.
Fool's Gold
Since Crystal Harris and Hugh Hefner are re-engaged after their 2011 split (when Harris ran off five days before the wedding), she's now been rewarded with yet another giant engagement ring.
Runaway Bride
Remember that time Playboy magnate Hugh Hefner was dating that young, attractive blonde?
No, not that one. Not that one either. Or that one. Or those two.