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That said, movie-Jackie is much better at improvisation than Bruce, so he'd be able to fake him out and take him by surprise if there's anything around for him to use (i.e. a stepping stool or a ladder). That said, Bruce would take this in an all-out brawl.
I remember reading something about Jackie being scared of really fighting Bruce, from his times as an extra in Bruce Lee movies. I could be wrong however.
Anyways, gonna have to go with Bruce Lee via more grounded fighting style (Jeet Kun Do was iirc, made to not be flashy and actually rather dirty, as he utilizes crotch shots).
Jackie probably is better at improvising and using random items in his surroundings to his advantage and overall seems versatile. But the guy comes off as a "jack of many trades and master of few" and his fighting style is just too flashy. Plus he does not have the best track record of taking down enemies with as few blows as possible. This could be due to him not fighting dirty and thus not hitting vulnerable spots on the human body as well as due to his hits simply not packing as much power as Bruce Lee's hits. Just look at his fights and in most of them, you see him taking down enemies with multiple hits and rarely does he ever one-shot or two-shot someone.
Bruce Lee has a minimalist skill set which gets the job done in any given situation against single or multiple opponents and it gets shit done without much fuss (minimal movements and flash but with tremendous speed and striking power). We see him regularly taking down enemies with only one or two hits and needs to do more only against the strongest. Even against the strongest enemies he's faced, he's gotten the job done quickly without screwing around.
In a fight against Bruce Lee, Jackie has to put him down quickly in as few blows as possible. It's either one/two powerful knock-out blow(s) or nothing. But I honestly don't see Jackie taking down Bruce Lee in only one or two hits. But I see Bruce Lee being able to take down Jackie in as few as two blows.
Jackie has slightly higher stats due to the fight with the Silent Monk and he tanks a lot of damage in all of his movie fights. I'd say Jackie will outlast Bruce Lee in a battle of attrition