• Hugh Hefner filed for divorce from wife Kimberly Conrad. The couple hasn’t really been together in more than 10 years. [Dlisted]—Why did she stay with him while he diddled Playmate after Playmate? Oh right, the money.
• John Mayer took to Twitter to dispel rumors he’s been hooking up with Kristin Cavallari. [Just Jared]—If you ever want to deny dating someone, say, “My Milli has never slam danced with her Vanilli.”
• Ashlee Simpson is on the cover of the October Redbook, and she told the magazine she doesn’t envy the freedom sister Jessica has since she’s single and childless. But, apparently, she said Jessica is envious of her being a mom. [People]—Don’t the rules of sisterhood say you shouldn’t tell a magazine your sis is jealous of you?

Of all the bunnies in the Playboy mansion, Holly Madison reigned supreme through most of the 2000s. Everyone’s favorite “Girl Next Door” and “Dancing with the Stars” contestant was Hugh Hefner’s primary girlfriend for six years, and many speculate that she broke his heart when they broke up, she moved out and then started dating Criss Angel soon after. But in the latest issue of Life & Style magazine, Holly reveals that she was always insecure about her looks—and that her insecurities shot to a whole new level when she started dating Hef. Hence, that was when she opted for plastic surgery. She says she was sensitive about her smallish chest (“I always stuffed my bra. In fact, I had a boyfriend for years, and we moved so slowly. We didn’t have sex for a long time because I had to gradually bring down my bra size so he wouldn’t find out”), but didn’t decide to get implants until after she moved into the mansion in 2001. In 2003, she had her nose done because “it photographed really big in front of my face. If I wanted to do anything in the entertainment industry, I needed to get it fixed.”

This quote really sticks out to me: “Living with Hef brought down my self-esteem a lot. I was comparing myself to the other girls…You have to look a certain way at the mansion.” [Life & Style via NY Daily News]

At a recent Playmate of the Year party, Hugh Hefner fessed up that he can’t actually tell his new twin girlfriends, Kristina and Karissa Shannon, apart. “I have one little trick, one has a little mark,” he said, motioning to his neck. “Other than that, I don’t know.” It sounds like that’s not the only thing Hef didn’t know. Both of these twins also have an arrest record. Oops.

To be honest Hef, we can’t tell them apart either. I never thought I would care, but I kinda miss the old “Girls Next Door” with their adorable quirks and distinct personalities. A friend of mine was at the mansion earlier this month and said Hef looked miserable. Maybe he misses Holly Madison? But then again, Hef didn’t ask our opinion. After the jump, a run-down on Kristina and Karissa.

Legendary rock n’ roll producer Phil Spector was just sentenced to 19 years in jail for murder. Although the prison guards took away his infamous afro wig, he was allowed to bring his iPod and a computer with him. So now, the inmate is a blogger…just like me. Dang, these internets are egalitarian! But what’s Phil got to blog about: prison slop, pooping in public, what really happens when you drop the soap? Actually, he’s been going on and on about his budding bromance with Wilson, a pet cockroach who likes to play chess. Uh, gross.

But in the Celebiverse, you don’t have to be behind bars to have a weird friggin’ pet. From a Blackberry stealing chimpanzee to a flock of flamingos, here are our favorite eccentric celebs and their even crazier animals.

Why else would she wear this homemade LA Lakers “dress” out in public? It’s sad when Holly Madison, Bridget Marquardt, and Kendra Wilkinson are Hef’s best-dressed girlfriends. [Los Angeles, 5/27/09]

Following in the footsteps of studs(?) Steve Martin, Burt Reynolds, Peter Sellers, and Jerry Seinfeld, Seth Rogan is about to become the 9th man to grace the cover of Playboy.  We Frisky gals will for sure be reading the March issue of the men’s mag for the articles….but we also hope sexy Seth gets his own spread.  Here’s are our five suggestions for how Playboy should photograph Hollywood’s hottest comedian…

In the January issue of GQ, Jennifer posed on the cover wearing nothing but a man’s tie to match her birthday suit. After seeing her cover, Playboy’s head, Hugh Hefner, said , “Is it just me or is Jennifer Aniston getting hotter?...Never seen her in this light before.” Whoa, easy there sparky!  But according to a Playboy spokesperson, Hef just had to ask if he could have her for his mag and offered her $4 million plus a bonus for sales that could earn her up to $10 million if she agreed to pose nude! Wow, I can barely get a dude to buy me a drink before we get nekkid. However, All American Aniston doesn’t literally want to be a “Girl Next Door.”  So, she turned Hef down, even though she told GQ “Yes” for a heck of a lot less dough.  Alas, the cougar has decided to keep her clothes on, this time.  But maybe she should reconsider, after all, that’s a whole lot of neck ties, Jen. [Celebrity Smack]

Holy Mother of God! The December issue of Playboy Mexico features what appears to be a sexy homage to the Virgin Mary, created to coincide with the Day of the Virgin of Guadalupe. In spite of the controversy the cover has caused, Playboy Mexico publisher Raul Sayrols refuses to apologize, asserting, “The image is not and never was intended to portray the Virgin of Guadalupe or any other religious figure. The intent was to reflect a Renaissance-like mood on the cover.” In that case, maybe the title shouldn’t have read: “We adore you, Mary!” In America, Playboy Inc. suggests a line may have been crossed, designating the shot the act of a vigilante licensee in Mexico, and offering an apology for the sins of their franchise. [Reuters]

Everywhere I turn, there’s a new set of twins, with four big boobs, two heightened libidos, and a camera. 2008 was all about two things: bisexuality and twins. Tila Tequila made a name for herself as a bisexual woman looking for love, while Lindsay Lohan came out and met the Ronson of her dreams. And everyone had twins this year—Brangelina, J. Lo, Nancy Grace, the list goes on. But in 2009, being bisexual and having twins isn’t going to get headlines—to be a STAR, you’ll need to be BOTH. Hugh Hefner just added two new Playmates to his mansion—twins Kristina and Karissa Shannon. This scenario makes my brain and my tummy hurt, because I can’t help but wonder if they get it on with Hef TOGETHER. Likewise, the new season of “A Shot At Love” is actually a “Double Shot” and features the “Ikki” twins, Rikki and Vikki, who are trying to find a perfect match amongst a pool of sexy beefcakes and hot lesbians. Meanwhile, at New York club The Box, the hottest featured act is the Porcelain TwinZ, who put on a fetish-burlesque show. What’s next? Mary-Kate and Ashley doing porn? “Sweet Valley High” erotica?

Hugh Hefner’s daughter Christie, who has sat at the helm of the $300 million Playboy Enterprises empire for the last two decades, stepped down from her post yesterday. The self-described feminist has faced a myriad of challenges on the job in recent years, including falling subscription rates for the company’s flagship magazine, in part due to the increasingly widespread availability of adult content on the internet. Most recently, there was talk of selling her father’s Playboy Mansion residence to raise cash for the corporation’s nose-diving portfolio. Three years ago, Christie was named one of the world’s most powerful businesswomen. Now, inspired by the Obama campaign, she’s making noises that suggest a shift into politics. So, do you think the former head of what some deem to be a pornographic magazine could get elected to a public office? [MSNBC]

More attention is paid when a famous couple calls it quits than when they tie the knot.  How come?  Because they’re more interesting duh!  While breakups are sad, there’s something about famous people that makes the 50 times more dramatic.  Perhaps it’s the various media outlets they trash talk to, the rumors surrounding them, or just the fact that everyone knows about it.  Here are our top ten splits in ’08.