It’s infrequent that we ever feel anything but nausea when thinking about Hugh Hefner, but, we’ll admit, we felt kind of bad when his fiancée, Crystal Harris, called off their wedding a mere five days before it was supposed to happen. It caused a pretty big splash when the 85 year-old announced that he wanted to take a stab at another serious commitment, let alone with someone 60 years his junior, so we maybe wouldn’t have blamed her if she left him for being a slimeball or for just being too old. But — stay with us, here — she left him because her first single “Club Queen” had dropped that day and had ridden the weird engagement fame wave as long as she needed to. Oh, honey…
The original princess of political scandal may be tame by today’s standards, but she was no bashful angel, either. Clinton’s P.Y.T. released a line of “Real Monica” handbags, became a Jenny Craig spokeswoman, and appeared in a host of made-for-TV specials with too-good-to-be-true names like Monica in Black and White and Monica’s Story. She hosted Mr. Personality in 2003, a Fox reality show which paired bachelorettes with masked male contestants and finally gained Lewinsky some (backhanded) praise from The New York Times: “after years of trying to cash in on her fame by designing handbags and other self-marketing schemes, Ms. Lewinsky has finally found a fitting niche on television.” Too little, too late, NYT; the show quickly tanked in the ratings and Lewinsky finally retired from her publicity-seeking days.
Back when Charlie Sheen was being paid to yell nonsense into crowds of mesmerized Americans — See: “Tiger blood!,” “Winning, duh!,” and other Sheenisms we’d like to forget — he caused perhaps the biggest splash with the news that he had a live-in harem. Two women, Natalie Kenly, a bikini model, and Bree Olson, a porn star, lived in his mansion as his “goddesses.” The three sounded perpetually giddy talking about their wonky sleeping arrangements and new-age domestic bliss, ushering in a new era of cultural head-scratching. But as Sheenmania died down, both the goddesses bailed out of the sinking ship. In fact, Olson’s quit porn and is planning to release an autobiography and a cookbook, which, of course, is a very obvious next step from “Charlie Sheen’s other lady-friend.”
Now, now, give us a chance on this one. We know Antoine Dodson is adorable and that he wasn’t the one responsible for producing the “The Bed Intruder Song,” which was scientifically proven to be the catchiest thing since the swine flu. When he started selling the song on iTunes and official Bed Intruder Halloween costumes, he really was just getting his fair cut of the runaway meme’s profits. However, we feel the need to backtrack a little: Dodson became famous because someone broke into his sister’s room and came into her bed. The original clip features him warning people against the neighborhood rapist, for crying out loud! We’re not so much shocked by the burst of cultural attention as we are empathetic towards the sister. Poor, poor girl. She’s the Jan Brady to Antoine’s Marcia.
Kim K’s the ultimate sex tape Cinderella story — who else could have turned one spicy night with Ray J into a career that’s most recently culminated in a four-hour E! wedding special — and made her a reported $15 million we should add. Not even William and Kate got the behind-the-scenes coverage that Kim and her new husband, Kris Humphries, got this month. Only months after her sex tape leaked, Kim saw an opportunity to build an empire and landed a pilot for Keeping Up with the Kardashians, opened up a clothing store with her sisters, created her own fragrance and jewelry line, and got her face on the front of every tabloid for the past four years running. She’s got the spotlight so tightly wrapped around her finger that it’s hard to remember a time when it wasn’t. Thank goodness we have Ray J to remind us.
The number of women on this list is getting flat-out depressing, but how could we not include Tiger Woods’ special friend, Rachel Uchitel? In 2001, she became a post-9/11 celebrity, after an iconic picture of her clutching a photo of her fiancé, who passed in the attacks, surfaced. Eight years later, she stepped forward to The National Enquirer about an affair she had with Woods at the Australian Masters, followed by a gaggles of other ladies. When Tigermania died, she began an affair with David Borneaz, making her frontrunner for the title of “most famous mistress on the planet!” Not only did she get a tremendous cash settlement form Woods, but Uchitel’s got a Playboy spread in the pipeline and appeared on season 4 of Celebrity Rehab With Dr. Drew .
Jon Gosselin, king of Ed Hardy and procreation, was the star of TLC’s Jon & Kate Plus 8, a show about Kate being a terrible mom, Jon being a terrible dad, and their poor, adorable eight children who paid the price for it. The two made a big stir with their divorce announcement in 2009, the speculative cause of which was Jon’s relationship with the 22-year old daughter of Kate’s plastic surgeon (?!), Hailey Glassman. Jon and Hailey gave happy couple interviews with Entertainment Tonight a few days before and after his daughters’ birthday, but broke up soon after. Jon also appeared on TLC’s American Chopper and, for a while, was rumored to have struck a business deal with Ed Hardy designer Christian Audigier, which Audigier later denied. Oh well, looks like Jon had some fun at Audigier’s birthday anyway!
Teen bride Courtney Stodden — yes, the 16-year-old who married 51-year-old X-Files and Lost actor Doug Hutchinson (his third wife!) — won’t let the world forget about her freaky love. She was kicked off Facebook (but recently had her account re-activated) for posting too many sexual pictures, but that hasn’t stopped her from playing Lolita to the paparazzi’s Humbert Humbert, what with all the porn star-grade photos she poses for pretty much anywhere she goes. Court and Doug two also have a reality show in a pipeline about their life together. Oh. Good. Here’s hoping it will be as entertaining (and by “entertaining,” we mean “horrifying”) as her Twitter feed.