Well, we're not even sure where to begin with this one. Kelly Killoren Bensimon who stars in the Real Housewives Of New York City doesn't necessarily come to mind when you think of a "hot mess", but fuck me she is THE biggest emotional mess we've ever seen. If you've ever been fortunate enough to sit through an entire episode (take our word - it's worth it), you'll know that she's a housewife (single mom) who does a bit of "modeling" on the side to pay for her psychiatric bills. Granted, she's in good shape for shitting out a couple kids, but she's kinda butch lookin' and we've always wondered if she's a Luann (transsexual in denial). We highly recommend you watch season 3 of the show cause it's something you'll wanna see before you die. At the end of the day, you gotta give a transgendered gal credit for still bein' a fame whore.
[Image via Bravo]