Tom Cruise and Cher
It may come as a surprise, but the worlds of Hollywood and music briefly converged when movie star Tom Cruise and musical icon Cher found themselves in a romantic entanglement. The unusual celebrity pair first crossed paths at Madonna and Sean Penn's wedding, a star-studded event that brought them together. At the time, Cruise was 22 years old, a striking 16 years younger than the legendary singer Cher.
Their connection deepened when Cruise and Cher attended a White House event focused on dyslexia, a condition both celebrities shared. Cher later revealed to Oprah Winfrey that she even spent time living in Cruise's apartment during their relationship. She described Cruise as shy, highlighting the surprising dynamic between these two high-profile figures.