Celebrities Who Worked in X-Rated Content Before Fame

You’ve gotta start somewhere, right? Some of your favorite celebrities got their start by taking it off. Yep, you read that right. Stars like Kim Kardashian, Jon Hamm, Cameron Diaz and Channing Tatum were involved in explicit content before their careers catapulted them to stardom.

While the Keeping Up With the Kardashians star was dating singer Ray J, the then-couple made a sex tape for their own personal enjoyment. That tape was leaked (without Kardashian’s consent) in 2007 — which she tried to sue for but eventually settled for $5 million. Kardashian then turned that somewhat negative press into a goldmine, pushing her career to new heights.

For the There’s Something About Mary star, it was a case of doing what was right for her career at the time. At age 19, Diaz appeared in a softcore adult film. Three years later, when she got her big break with 1994’s The Mask, she tried to get the movie shelved.

The photographer who shot the footage, John Rutter, allegedly tried to sell the pictures and video to her for $3.5 million before attempting to sell the content to prospective buyers. Diaz then sued him, claiming he blackmailed her. He was sentenced to three years in prison in 2005.

You probably know notorious heartthrob and Mad Men star Hamm from his award-winning turn as Don Draper. But long before he suited up as an advertising executive on the 2007 series, Hamm worked as a set dresser for pornographic films. The Bridesmaids star took the gig during the early days of his acting career — and maintains he never actually got naked on set.

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When it comes to Magic Mike star Tatum, art truly imitates life. He worked as an exotic dancer when he was 19 years old — and his past served in part as inspiration for the dance-based comedy-meets-drama film. However, Tatum didn’t have the best things to say about his experience with stripping, calling it “seedy” in 2015.

There are, of course, celebs who have made transitions into the adult film industry — like Boy Meets World‘s Maitland Ward and Saved By the Bell‘s Dustin Diamond — but these folks made their mark early on.

Scroll through the gallery to see which of your favorite celebrities have NSFW pasts.

Kim Kardashian

Kim’s story is pretty famous. While working as Paris Hilton‘s assistant during her rise to fame, the young starlet and her then-boyfriend made a sex tape — which ended up circling the internet and making Kim ~famous~ overnight. Allegedly, the footage was leaked without the socialite’s consent … but she turned it into a positive.

However, she dished about how awkward things got during a 2018 interview with author Bret Easton Ellis. “Once you go through it and you have those conversations with your parents and grandparents and everyone that you’d be really embarrassed about it with, I think you get to a point where you’re like, ‘Okay, we’re dealing with this legally, and it’s time to move on,'” Kim said.

Cameron Diaz

The Charlie’s Angels actress starred in a softcore erotic film before her acting career took off. When she started blowing up in movies like The Mask, she tried to stop the circulation of the footage — but the holders of the video allegedly demanded $3.5 million from her to bury it. The starlet, who has since retired from acting, has never spoken publicly about the film.

Sasha Grey

Actress Sasha Grey has starred in The Girlfriend Experience, Entourage and I Melt With You, among others in her impressive acting career. But she started out in Hollywood already famous — as a legendary porn star. She spent five years at the top of her adult entertainment game before retiring from porn in 2011.

David Duchovny

X-Files star David Duchovny also appeared in The Red Shoe Diaries — more than once. In fact, he hosted the series for a whopping 66 episodes from 1992 through 1996. But to be fair, he never once stripped down on the show.

“Ultimately, I could have told myself many things, but I needed a job. I wasn’t being offered a bunch of stuff,” David said in MEL Magazine‘s 2019 oral history on the series. “It was, “Wow, a job!” And possibly a job in the future as the episodes spun out.”

Helen Mirren

Legendary actress Helen Mirren appeared in the controversial film Caligula early on in her career. The 1979 roman epic was banned in several countries for gratuitous sexual content. The longtime actress has spoken highly of the film, calling it a “an irresistible mix of art and genitals” shortly after shooting.

“I’ve never opened my mouth to denigrate Caligula,” she told The New York Times. “I was pretty young when I made that — not physically so much as experienced in film. And you know what? It was a great experience. It was like being sent down to Dante’s Inferno in many ways.”