Brad Pitt and Christina Applegate
Long before the era of Brangelina, Brad, and Jen, there was a lesser-known but intriguing chapter in Brad Pitt's romantic history involving actress Christina Applegate. In this case, it was more Christina and Brad, as Applegate was already a household name thanks to her role on the popular sitcom "Married... With Children."
Adding a touch of amusement to their brief connection, Brad Pitt and Christina Applegate publicly appeared at the MTV Movie Awards in 1989. However, the two did not leave the event together despite their joint attendance. In a twist of fate, Applegate reportedly ditched Pitt in favor of spending time with Skid Row's Sebastian Bach instead, offering a glimpse into the unpredictable world of celebrity relationships during the '80s.