In 1960s Hollywood, there was a popular legend floating around that involved Bruce Lee and Frank Sinatra. It was indicated in Bruce Lee: A Life by Matthew Polly that the story contributed (at least to some degree) to the martial arts actor’s success as a kung fu teacher in Hollywood. However, that doesn’t necessarily mean it is true.
Though Lee was a long way away from being a movie star, he had quite a few friends and acquaintances in the Hollywood area during the 1960s. Due in large part to word of mouth and the skills he showed off at kung fu demonstrations, Lee was well-liked by numerous celebrities, and many paid him to teach them Jeet Kune Do kung fu. As a result, Lee was often included in the social circles of director Roman Polanski, celebrity hairstylist Jay Sebring, A-list movie actors James Coburn and Steve McQueen, and more. Because of the time Lee spent with them, there are all sorts of Hollywood stories about the kung fu icon and his run-ins with other household names.
Polly’s book details a story that’s become a frequent topic at Hollywood parties. Rumor has it that Lee accepted – and passed – a challenge issued to him by the iconic singer Sinatra. The story alleges Sinatra developed an interest in kung fu after filming a martial arts fight scene in The Manchurian Candidate. However, he was skeptical about it and invited Lee to his hotel suite in Las Vegas to judge Lee’s kung fu for himself. Supposedly, the two arranged a test that would ensure no one got injured.
At Lee’s suggestion, they agreed he would try to knock a cigarette out of the mouth of one of Sinatra’s two bodyguards before either man – both of them much larger than Lee – could stop him. Sinatra agreed to Lee’s terms and told his bodyguards not to hurt him, but that it would be okay to “knock him on his a**.” As the story goes, Lee leaped across the room and used a high kick to knock the cigarette from one of the bodyguard’s mouths, shocking Sinatra in the process.
According to Polly’s book, it’s likely this legend evolved from another Hollywood story, this one being about Lee and a different 1950s singer, Vic Damone. There are different versions of the challenge, but they all involve Lee impressing Damone by taking away a cigarette from Sammy Davis Jr.’s bodyguard. Hollywood screenwriter Stirling Silliphant, who was one of Lee’s many celebrity friends and students, said he actually sought friendship with Lee because of this, even though he too wasn’t sure if any version of it had really happened. Silliphant said these legends were “circulating all over Hollywood” and as Polly points out, it only helped Bruce Lee’s image that neither Sinatra nor Damone ever debunked it.