This competitiveness was on full display in a now-legendary game of table tennis between the stars in December 1985. Jackson showed up with his bodyguards at Samuel Goldwyn Studio in West Hollywood, where Prince was putting the final musical touches on
Under the Cherry Moon. After some small talk, Prince challenged Jackson to a game of ping-pong. Jackson had hardly played before but said he’d give it a try. Work stopped in the studio as people gathered around to watch the two superstars play.
Prince went easy at first, but before long his competitive streak took over and he began slamming the ball past (and at) a hapless Jackson. “He played like Helen Keller!” Prince later joked to friends.
Jackson recovered by chatting up Prince’s then-girlfriend, actress Sherilyn Fenn. “Michael knows how to handle himself,” recalls Prince’s recording engineer, Susan Rogers, “and he didn't seem to care [about the game]. [He] started flirting with Sherilyn Fenn, who was visiting Prince in the studio. Prince was pacing, but he wasn't going to get into the game of flirting back. They said hasty goodbyes.”
Prince and Michael Jackson: The Rivalry and the Revolution