Wilmer Valderrama’s Horrifying Howard Stern Interview Resurfaces After Danny Masterson Sentencing.

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After That ‘70s Show‘s Danny Masterson was sentenced to 30 years to life in prison for two counts of forcible rape, co-stars like Wilmer Valderrama are back in the spotlight. Mila Kunis and Ashton Kutcher were among the 50 people who wrote letters to the judge vouching for the character of the disgraced actor (and have since apologized in a social media video). Debra Jo Rupp and Kurtwood Smith, who played Kitty and Red on the show, respectively, also submitted letters on Masterson’s behalf. Masterson’s That ‘70s co-stars Topher Grace, Wilmer Valderrama, and Laura Prepon did not pen letters of support.

Masterson’s conviction and sentencing has shined a spotlight on the culture of That ‘70s Show, including Kunis’s admission that Masterson once bet Kutcher $10 to French kiss her during a scene when she “was a 14-year-old little girl,” in Kunis’s words, and the way Grace’s departure from the series was reported at the time to paint him as the diva outlier of the group.

And then there’s the matter of Valderrama’s Howard Stern interview — which, even by Stern standards, was (and is) notoriously gross.

Before the now NCIS actor met — and had a child with—  his fiancee Amanda Pacheco, he opened up about his womanizing ways during a tasteless interview on Stern’s Sirius XM radio show in 2006.

It’s a disturbing 50-minute interview that has to be heard to be believed. During it, Valderrama brags about how Ashlee Simpson is good in bed, commenting, “It was a little louder than that,” as a whining sound-effect plays. When Valderrama tries to explain “what helped” him gain the attention of women, Stern chimes in “roofies,” to which the actor jokingly replies, “One… that’s the silent fact.” He also boasts that he took ex Mandy Moore’s virginity, claiming, “The sex with Mandy was good, but it wasn’t like warm apple pie.” Yuck.

Valderrama proceeds to give Jennifer Love Hewitt an eight out of 10 sex rating, boasts about being “cursed with this gift” of having a giant penis, says he doesn’t want to be with Paris Hilton because he won’t “do things that have been done,” and describes ex Lindsay Lohan’s breast size and shaving routine yet can’t seem to remember if a girl has ever rejected him. Toward the end of the deeply unsettling radio talk, Valderrama dishes on his MTV reality show Yo Momma, where adult men compete against one another by telling elementary school-level “yo momma” jokes (yes, this was really a thing), and plays “fuck, marry, kill” with his celebrity exes.

In an interview with Elle published months after the Stern chat, Moore attempted to clear things up, saying Valderrama’s arrogant remark was “utterly tacky, not even true, and it hurt my feelings because I like him.” (Valderrama’s representatives did not provide comment to Rolling Stone prior to publication.)

Last year, Demi Lovato released her single “29,” which alludes to the 12-year age gap she had with ex Valderrama when she was only 17. In an interview with Zane Lowe on his Apple Music show, Lovato said a recent vacation after turning 29 helped her “put things into perspective.”

“I would be lying if I said I didn’t have a ton of anxiety about putting out this song,” Lovato told Lowe. “I just said, ‘I have to go for this. I have to own my truth.’”

Kalia Richardson

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