Despite Bruce Lee’s skills as a fighter, rumors have circulated since the 1960s about the martial arts legend losing two of his fights. Given the remarkable speed and skills he’s displayed in his films, it’s easy to see Lee as someone who won all of his fights. It’s partially for this reason that Quentin Tarantino’s decision to have Lee lose to Brad Pitt’s character in Once Upon a Time in Hollywood courted so much controversy.
Through roles in just five kung fu movies, Lee developed a reputation as the greatest martial arts movie actor of all time. And not only was Lee respected for his onscreen image but he was viewed as a martial artist of seemingly unsurpassed skill in real life as well. Over the years, there have been numerous discussions about how Lee would stack up against professional fighters. But since Lee never competed at this level, this will remain open to speculation. However, several Hollywood tales and public demonstrations have shed light on his capabilities. As for the fights he’s been involved in, most of these stories end with Bruce Lee winning.
Interestingly, there have been two fights that Bruce Lee was rumored to have lost, which were against Hollywood stuntman Gene LeBell and Chinese martial artist Wong Jack Man. It’s worth noting that while there’s evidence to show that both fights did indeed happen, there’s not enough to prove outright that Lee lost either one. It would seem, based on the accounts of what took place, one wasn’t a true fight (nor was it under fair conditions), and in the case of the other, there are too many conflicting stories to declare a real winner.
The aforementioned incident with Gene LeBell happened on the set of The Green Hornet [via South China Morning Post]. Supposedly, the show’s stunt performers weren’t happy with Lee’s rough approach to Green Hornet's fight scenes so they convinced LeBell to go up against him. Instead of starting an actual fight with the actor, LeBell used his size and strength to force Lee into a headlock before proceeding to carry him around the set on his back. Unable to get free, Lee shouted at him angrily until he was finally put down. Since this was the extent of the conflict, it may not be fair to call this a true loss for Lee, especially since LeBell was able to grab him by catching him by surprise.
As for the fight with Wong Jack Man, it was of a much more serious nature and can actually be classified as a martial arts showdown. According to Bruce Lee’s wife, Linda Lee Cadwell, Wong Jack Man fought Bruce Lee to get him to stop teaching Chinese martial arts to Americans. Wong stated that the fight was called off after 20 minutes because Lee was too exhausted to go on. If Wong’s story is accurate, that could very well be the closest Lee ever came to losing, but that claim has never been proven. William Chen, who witnessed the fight, said it ended in a tie, whereas Cadwell has said that despite some difficulties dealing with Wong’s style, Bruce Lee managed to win in less than three minutes.