We’ve already brought you Brad Pitt selling Pringles. But how about the good old days when Brad acted his young heart out? Well, you could say acted, but his talents back in the ’80s do not reveal the success to come. You can search around and find some embarrassing clips from his stint on Dallas, but I thought I would throw up a little pirate flavor.

Back in 1988, Pitt popped up as a high school student in an episode of 21 Jump Street. Along with Captain Jack Johnny Depp and Peter DeLuise (who is currently a director on the new Canadian show jPod), you’ll also notice Cheryl Pollak — who played smartie Paige Woodward in Pump Up the Volume. So her brother spends a night in jail, with his super-saucy mullet, and letterman-jacket Pitt teases him mercilessly because the bad dude partied without him. I have to say, Pitt’s voice sure got deeper over the years. Brad totally could’ve pulled off a cross-dressing role back then.