Brad Pitt's 10 Hottest Hook-Ups

Jill Schoelen

When: 1989

Schoelen co-starred with Pitt in Cutting Class, a slasher horror flick that will forever be remembered only for being Pitt's first starring role. Schoelen will be remembered for (if anything) being Pitt's first rumored fiancé. 

Smash Probability: We bet they were engaged in something.

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