Charlie Sheen and Kelly Preston
Kelly Preston, who makes her second appearance on this list, was romantically involved with the ever-controversial Charlie Sheen. Sheen, known for being the brother of Emilio Estevez and a fellow '80s star, dated Preston toward the end of the decade. Their relationship progressed to the point where they became engaged. Still, their three-year romance ultimately met a tumultuous end when an alleged incident occurred in which Sheen reportedly shot Preston in the arm.
This incident garnered significant tabloid interest, and for years, both partners found themselves embroiled in disputes over the details. In 2011, Kelly Preston clarified her stance, telling TMZ that Charlie Sheen did not shoot her, adding an intriguing layer to their complex history.
