Years active in the WWE: 1993-present
Sean Waltman, the man who gave '90s teens the perfect comeback when their moms told them to clean their rooms, has the dubious distinction of appearing with Chyna in a porno. He also had the dubious distinction of getting booted out of the Surreal Life house by Da Brat and Verne Troyer after trying to reconcile his relationship with the ex-WWE superstar/current porn star because she'd learned that four years earlier he was knocking boots with Jenna Jameson, ex-porn star/current Mrs. Tito Ortiz.
He apparently tried to kill himself by hanging in a Mexico City apartment. Like a lot of this lists' members he entered rehab. And like a lot of rehab patients in 2011 he was found relapsing with a controlled substance. He also suffered from a painful anus (not a medical term) which literally almost killed him. It happens about 28 seconds into this video. Yikes.