Fight fans love a good rivalry, and the Gracie guys have seen their fair share of epic showdowns. Perhaps the most famous Gracie match occurred in 1951, when the highest-ranking judo experts in Japan sailed to Brazil to challenge a nearly 38-year-old Helio.
After choking out their second-best fighter, Yuko Kato, Helio was set to face Masahiko Kimura, the greatest judoka on the planet. As Kimura had 80 pounds on Helio, the Brazilian was predestined to take a major beating. But ever a champion, Helio made it to the second round before Kimura applied his trademark move, the kimura. Carlos Gracie threw in the towel on his stubborn brother's behalf, but while Helio lost, an impressed Kimura awarded him the rank of sixth dan in judo.
The next great rivalry came in 1955, when Helio fought Waldemar Santana, a student who'd turned against the Gracies. It was master vs. apprentice, only the pupil had 40 pounds on the teacher. After a nearly four-hour war, Santana knocked Helio out with a face kick. Furious, Carlson Gracie (son of Carlos) avenged the family name in four separate bouts, earning one draw and three wins. The Santana-Gracie rivalry spilled over into the next generation when Santana pitted his supersized student, Rei Zulu, against an 18-year-old Rickson. Zulu had nearly 45 pounds on the teenager, but after getting tossed out of the ring three times, Rickson won via rear-naked choke.
The most colorful Gracie rival, however, has to be Kazushi Sakuraba. Famous for wearing luchador masks and drawing fake muscles onto his body (and they say working out is hard), Sakuraba was known as "The Gracie Hunter." After all, he'd defeated three separate Gracies, including ex-UFC champion Royce. Naturally, everyone wanted to see the Japanese wrestler fight Rickson. Unfortunately, the dream match never materialized, as Rickson withdrew after the tragic death of his son.