3. Danny Masterson
As we discussed previously, actor Danny Masterson was convicted of sexually assaulting multiple women. His sentence was 30 years to life, and during the period where he was sentenced, a 2004 interview on “Late Night With Conan O’Brien” showed Masterson responding to a joke about his accent with a vulgar and inappropriate joke. O’Brien joked back that he would be “caught soon,” but little did either man know that the statement would predict the future.
2. Britney Spears
After breaking up with Justin Timberlake in 2003, Britney Spears was interviewed by Diane Sawyer, who asked the starlet a stream of uncomfortable questions. She pressured the 21-year-old to answer questions about the breakup and appeared to defend Kendel Ehrlick, the former First Spouse of Maryland, who said she would shoot Spears if she had the chance. The entire interview came off as an abusive interrogation, one during which Spears started to cry.
1. Bill Cosby
Bill Cosby’s court case lives on in infamy these days. The celebrity dealt with dozens of allegations of sexual assault throughout the years when it came to light that he drugged his victims before assaulting them. It’s not too surprising when you look at a 1991 interview with Larry King, where Cosby casually referenced spiking women’s drinks. He jokes to the talk show host about Spanish Fly, a supposed aphrodisiac, which he would drop into a woman’s drink so that he could do whatever he wanted with her.