Shooter: Michael Jordan
Game: Game 5, 1989 Eastern Conference Quarterfinals
Date: 5/7/1989

Before he made a career of torturing the Knicks and Jazz, Michael Jordan made his bones burying the Cleveland Cavailers. Winless against Cleveland in six games that season, Jordan made good on his promise of an upset in classic fashion. This shot would be the first of many playoff game winners to come for MJ, and the Cavs wouldn't be the same until another high-flying No. 23 broke their hearts 21 years later.