That new Chanel No. 5 commercial featuring Brad Pitt is hilarious -- and it got us thinking about what he was up to before he became famous. In today's Way Back When, we take a look at the earlier roles of one of America's most famous leading men.


Way back in 1988, Brad Pitt played Randy, boyfriend of Charlie on the long-running nighttime soap opera 'Dallas.' Charlie was the daughter of Priscilla Presley's character, and in this episode (shown below), her husband Ray is allowing Randy to move in with the family, but he's setting some ground rules -- double or group dates only! No studying in each other's bedrooms! Comb your hair, mister! Also, we wonder if Brad Pitt ever ages or if he just, you know, evolves?

'21 Jump Street'

If you've ever wanted to see Brad Pitt and Johnny Depp share the screen, then you needn't look further than this episode of the classic '80s TV series '21 Jump Street.' Pitt plays a jock-ish bad boy type (obviously) and Depp is trying to figure out if his buddy, who just got out of jail, is a cat burglar. But more importantly: Brad Pitt and Johnny Depp once acted in something together and the universe didn't implode.

'The Dark Side of the Sun'

This is a movie that time apparently forgot because Fox Video released it in 1997 -- nine years after its initial release -- to capitalize on Pitt's hotness. It's billed as an "incredible love story," but this trailer is ridiculous. Watch Brad Pitt say "this has been the most beautiful day of my life." Watch Brad Pitt skip across the water. Watch Brad Pitt stand on a beach. We have no idea what the title of this movie is supposed to mean and we don't want to look at the official plot on IMDB because we're scared we'll ruin how gloriously and mysteriously awful this trailer is.

Levi's Commercial

In 1991, Brad Pitt was a very bad boy in this Levi's commercial for the brand's famous jeans. You know this commercial is dirty because it opens with the image of a cockroach -- gross! But hey, there's Brad Pitt in his underwear, so we're making some progress. He's escorted out of the jail, which is in the desert, and a sexy lady comes to pick him up and gives him some jeans to wear because the harsh desert environment is not healthy for his naked legs. Clearly this is not his girlfriend. This is a dermatologist and she has some serious opinions about skin care.

Pringles Commercial

Apparently still struggling to make a name for himself in the early '90s with movies like 'Cool World' and 'Thelma & Louise,' Pitt continued his commercial jobs with this 1992 ad for Pringles, which was apparently put together by someone on meth. In it, Pitt and his surfer bros are out of Pringles and their car breaks down. And Brad Pitt is wearing the most unfortunate combo of green shorts and blue Converse hi-tops we've ever seen. Okay, we've never seen this combo. Not even Zack Morris could touch that. The tag for the commercial sells Pringles as the "fever reliever," but we were pretty sure that was Tylenol.