Charismatic was a 30-to-1 shot, but he brought home $886,200 when he defeated Menifee by a neck. After winning at the Preakness Stakes, he had to win just one more race to win the Triple Crown, a feat no horse had accomplished in 21 years. No longer an underdog, Charismatic went into Belmont Stakes a 2-to-1 favorite, only to come in third.

Michelle Wilkins/AFP/Newscom
Jockey Chris Antley (r.) rides Kentucky Derby winner Charismatic across the finish line with his finger pointing number one to second place finisher Menifee and jockey Pat Day (l.) on May 1, 1999 at Churchill Downs in Louisville, Ky.