Event: UFC 1 11/12/1993
Winner: Royce Gracie
Winning Move: Rear Naked Choke
Of all the Gracies, Royce is the most well known. He was the first person admitted to the UFC Hall of Fame. He was also the winner of UFC's 1, 2 and 4. He would have won UFC 3 had he not had to throw in the towel due to injury.
UFC 1 was a bizarre event. There were almost no rules and it was bare-knuckle. No one in America had ever seen BJJ so to watch this scrawny, 178-pound guy manhandle seemingly superior opponents was mad confusing.
Ken Shamrock was a yoked-up wrestler fresh off the boat from Japan where he was a star submission fighter in the art of Pankration. Everyone was convinced he was going to snap Gracie's leg. Less than a minute into the match Shamrock tapped out four times definitively. When Gracie let go of the choke Sham-rock pretended nothing had happened and kept fighting. Get embarrassed on pay-per-view TV much?
Thanks to Gracie's performance at UFC 1, Brazilian Jiu-Jitsu was validated as the most effective martial art and MMA is now a multi-billion dollar industry.