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Risque! These Celebrities Had NSFW Pasts Before Becoming Big Stars: Kim Kardashian, Cameron Diaz, More

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 KardashianJon 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.

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.