To make ends meet while trying to woo Hollywood's gatekeepers as a wannabe actor, Brad Pitt chauffeured around strippers. It might have seemed unconventional to literally traffic sex workers, but Pitt had a name in the skin game himself back in his University of Missouri days.

He was part of a group called the Dancing Bares, an all-male frat-adjacent club, somewhat akin to Chippendale's. They would perform strip tease dances for girls on their birthdays. "When a girl from one of our sister sororities turned 21, the Bares would put her in a chair and come out butt-naked with pillowcases on their heads and do a choreographed dance for her," one of the club's former members, Thomas Whelihan, told In Touch Weekly in 2007. He dropped out of college just two credits shy when he realized he could just leave.

Pitt arrived in Hollywood in a similar way to how he arrived on screen in breakout role in Thelma & Louise. "My coming out here [to Hollywood] is the classic story, but it was such an adventure it was cool," he told photographer Karen Bystedt in May 1989. "I had $300 to my name. My car, a dented silver Datsun, which I named 'Run Around Sue,' was loaded up. I just remember saying, 'Yeah!' every time I would drive past a state line. I was so excited."

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Once he got there and for half a year afterwards, Pitt split an apartment with eight other guys. "I did all sorts of odd jobs, like dressing up as a chicken and being a delivery boy and driving strippers around. I did anything that was flexible, so I could figure out how to get into this frickin business. I started doing extra work the first week I was here. I mean, I didn't even know you had to have a head shot."

"I did all sorts of odd jobs, like dressing up as a chicken and being a delivery boy and driving strippers around."

Despite all of the jobs he could cram onto his resume, it was transporting sex workers in a limousine that gave him the keys to his dream job. "I was driving strippers around on weekends to make extra money. I'd take them to bachelor parties. I did that for about two months and then I couldn't hang with it. But then on the last night I drove, one of the new strippers told me about an acting class that her friend Charlie Sheen went to. I figured, if it's good enough for Charlie, it's good enough for me."

Pitt went to the class and met a girl who had an audition lined up with Triad Agency. (Triad later merged with William Morris Agency — now William Morris Endeavor — in '92). "She asked me if I'd do a scene we prepared for class in front of all these agents. I said, 'Yeah, I guess so, whatever.' Boom. I got signed." The shocking twist: his scene partner didn't.

Photo via BFA