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A Nearly 20-Year-Old Danny Masterson Joke (And Conan O’Brien’s Response) Sure Hits Differently After His Rape Sentencing

This week, Danny Masterson’s decades-long prison sentence ended a long legal saga (and hopefully also ended a pattern of harassment by Scientology goons) for his rape victims. The That ’70s Show star reportedly blew a kiss to wife Bijou Phillips in the courtroom and has vowed to appeal the sentence. In the immediate aftermath of the sentencing announcement, however, a nearly decades-old Conan O’Brien clip has been making the rounds because it hits rather uncomfortably now.

It’s worth noting again that the two forcible rape convictions involve 2003 events at Masterson’s Hollywood Hills home. And in 2004, the That ’70s Show star visited O’Brien, where the subject of accents came up. Even after transplanting to California, Masterson found the pronunciation of certain words would stick around from his Long Island days. That led to a story about fellow Scientologist Bodhi Elfman giving Masterson hell, as he told Conan: “He always teases me and he says, ‘Hi, my name is Danny Masterson, would you like to touch my balls.’”

In this clip highlighted on Twitter by the WuTangKids account, Conan inquired about why on earth Masterson would ask for that. Masterson had a wiseass comeback: “I mean, you got ’em, you know what I mean? Everybody should grab.” And Conan (in classic Conan comeback fashion) quipped, “I’ve heard about you… you’ll be caught soon, I know you will.” Masterson agreed, although no one had any idea at that point how accurate that would turn out to be. Looking back, this is a real head shaker of a conversation.

In May, Masterson was found guilty of two of three counts of rape by force or fear. 20 years after those crimes, he’s 47 years old, and he most likely won’t surface from prison until age 77. During the sentencing hearing, the judge told the actor, “You are not the victim here. Your actions 20 years ago took away another person’s voice and choice. Your actions 20 years ago were criminal.” Prior to that moment, one of Masterson’s victims called out his former DJ moniker, DJ Donkey Punch (yes, that would refer to the dangerously violent sexual act).

The Conan clip isn’t the only one that looks especially sketchy these days. Here’s a clip from a James Corden interview where Masterson declares, “I probably have more photos of Commando Kutcher here naked in the club than probably anybody.” It was awkward then, and it’s worse now.