As an 18-year-old young pup rookie out of Lower Merion High School in Pennsylvania, Bryant became the youngest player in NBA history to win the Slam Dunk Contest. It also marked the only time Bryant ever competed. Admittedly, the competition back in 1997 wasn’t exactly stiff. Bryant beat out fellow competitors Ray Allen, Michael Finley, Darvin Ham, Bob Sura and Chris Carr (who?). No disrespect to Kobe, but his dunks in this competition pale in comparison to today’s high flyers like Aaron Gordon and Zach LaVine. Despite winning five titles during a string of dominance throughout the 2000s, Bryant only garnered one NBA Most Valuable Player award during his career – in 2008.