HO – ‘If that last punch from Tyson hits, then the whole Ip Man series ends there’: IP Man vs Mike Tyson in a three-minute fight in the movie IP MAN 3 (2015)

11 Times We Got to See Martial Arts Legends Fight Each Other in Movies

Ip Man 3 is the third film in the popular Ip Man series of Hong Kong martial arts movies. It sees the titular martial arts master taking on a dastardly land developer and his team of sadistic gangsters.

The big fight in this movie takes place between Donnie Yen and pro boxer Mike Tyson. Their frightening three-minute brawl is a hair-raising highlight in a movie loaded with beautifully choreographed duels.

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Bruce Lee vs. Robert Wall – Enter the Dragon (1973)

Bruce Lee and his co star in Enter the DragonGolden Harvest

Warner Bros.

Enter the Dragon is a martial arts masterpiece, and the last film that Bruce Lee completed before his sudden death in 1973. It follows the kung fu master on a mission to capture a gang leader who killed his sister. He winds up having to compete in a fighting competition in order to get closer to his target.

Though there are many amazing fight scenes in Enter the Dragon, the most legendary is the one that pits Bruce Lee against his real-life friend and sparring partner, Robert Wall. Although not as well known as some of the other fighters on this list, Wall was no slouch; the martial artist trained under none other than Chuck Norris, and his incredible skill is apparent in this fight scene from Enter the Dragon.

Cynthia Rothrock vs. Bolo Yeung – Tiger Claws (1991)

Tiger Claws scene

MCA/Universal Home Video

A must-watch action extravaganza for fans of Cynthia Rothrock, lovable B-movie Tiger Claws offers a perfect balance of adrenaline-pumping gunplay and martial arts mayhem. It’s about a serial killer, played by competitive bodybuilder and martial artist Bolo Yeung, who’s been clawing up famous fighters in New York City.

The monumental moment from this movie pits martial arts legends Rothrock and Yeung against each other in a thrilling battle. Though it ends inconclusively, the epic battle picks up again in the delightfully cheesy sequel, Tiger Claws II.

Jackie Chan vs. Ken Lo – Legend of the Drunken Master (1994)

Legend of the Drunken Master scene

Golden Harvest

One of the most fun martial arts flicks ever made, Legend of the Drunken Master (also known as Drunken Master II), tracks Jackie Chan’s “Drunken Master” as he puts the intoxicated beatdown on loads of bad guys in Chan’s typical silly yet impressive fashion.

The greatest moment from this movie is when the martial arts legend squares off against fellow fighter and member of Chan’s famous stunt team, Ken Lo. Their battle is simultaneously inventive, super stylish, and edge-of-your-seat intense; Lo’s careful precision meets its match with Chan’s loose, “drunken” style, and the resulting fight is kung fu movie bliss.

Donnie Yen vs. Sammo Hung – Ip Man 2 (2010)

Ip Man 2 Mandarin Films

Mandarin Films

Ip Man 2 is the rousing sequel to Donnie Yen and Wilson Yip’s 2008 modern classic Ip Man. It tracks martial arts master Ip Man as he attempts to relocate to Hong Kong and faces resistance, corruption, and bitter rivals.

According to Collider, “Despite being a staple in the ’90s martial arts scene, Donnie Yen didn’t truly blow up in mainstream popularity until the release of Ip Man in 2008.” Indeed, the Ip Man series features many of Yen’s finest moments on the silver screen, including the one in which he battles an old master played by the venerable Sammo Hung. The two screen legends face off in a duel full of classic, chill-inducing Hong Kong movie magic, in a scene that is as exciting as it is deeply moving.

Jean-Claude Van Damme vs. Bolo Yeung – Bloodsport (1988)

Van Damme in Bloodsport

The Cannon Group

Bloodsport is a martial arts classic starring the great Jean-Claude Van Damme. Equal parts cheesy schlock and extremely effective beat ‘em up entertainment, it’s no wonder why Bloodsport is everyone’s favorite Van Damme movie.

Although Van Damme faces a number of worthy opponents during his run at the Kumite martial arts tournament, he meets his match in Bolo Yeung. The duel between these two fighting icons is nothing short of perfection, as their contrasting styles entertain, while the life-or-death stakes captivate.