Christian Slater and Winona Ryder

Christian Slater and Winona Ryder, co-stars in the black comedy and high school satire "Heathers," kindled a brief romance after filming concluded. He had made his film debut several years prior in "The Legend of Billie Jean" and continued to build his career, eventually taking on the leading role in "Mr. Robot."

As for Winona Ryder, her career as an actress endured beyond the '80s, but she also faced personal challenges in the '90s. The star encountered legal troubles when she was arrested for shoplifting in 2001, a period during which she grappled with prescription medicine issues. Naturally, her experiences with fame, scrutiny, and personal struggles became fodder for the tabloids, casting a shadow on her otherwise successful career.

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