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Introduced in Ip Man 1
Ip Man (Master Ip)The titular character. Ip is a Wing Chun master whose house was seized by the Japanese. Played by Donnie Yen.
- Berserk Button: Will NOT stand down when defending the Honor of Chinese Warrior Culture. He also doesn't take kindly to those who threaten his family.
- Doting Parent: Becoming poor made him closer to his family, and comes to realizes how much he loves them over Martial Arts. He even asks Master Hung in the second film "Which is more important; our battle, or having dinner with your wife and children?"
- Improvised Weapon: A master of this. First he uses a duster and later he uses a stick. Both against Jin.
- The Heart: Is willing to help anyone in need in spite of his own poverty.
- Misery Builds Character: And makes you a more loving father.
- Not So Stoic: He was often calm and collected but he finally loses it when he saw Liu being shot trying to pick up a bag of rice he won.
- One-Man Army: He can literally defeat dozens of martial artists single-handedly.
- Parental Neglect: He seems to be this at first regarding his son. To the point that his wife called him out on it.
- Proud Warrior Race Guy: Dosen't stop him from being a gentleman and a total sweetheart, though.
- Rapid-Fire Fisticuffs: His rolling punches pack a serious wallop.
- Real Men Wear Pink: Granted he is garbed in black 99% of the duration of both films and never literally wears pink, but it's mentioned a few times that Wing Chun was invented by a woman. The name itself means something like "eternal springtime" or "spring chant" depending on who you ask.
- Riches to Rags: He started out a rich man, then was forced to live in abject poverty when the Japanese occupied Fo-Shan.
- Showy Invincible Hero: While he always curb-stomps his opponents, at least in the first film, he did it with such a style.
- Simple, yet Awesome: The fundaments of Wing Chun Kung Fu.
- Smoking Is Cool: When he is at ease.
Cheung Wing-singIp Man's wife, played by Lynn Hung. She disapproves of her husband always fighting and wants him to spend more time with his family. She has two sons: Ip Chun, played by Li Chak, and Ip Ching, born at the end of the second film.
- Incurable Cough of Death: She starts getting abdominal pains in the third film and was eventually diagnosed as having cancer. She died after the events of the film from it.
Master LiuA martial artist teacher who had a friendly fight with Ip. Played by Chen Zhihui.
- The Worf Effect: He was easily defeated in his first two fights on screen. By the time he actually defeated someone, it was too little too late.
"Crazy/Zealot" LinIp's friend who runs a teashop. Played by Xing Yu.
- Hot-Blooded: Deconstructed; his passionate hate against the Japanese ended up getting him killed by Miura (who didn't want to kill him in the first place).
- Too Dumb to Live: Despite the fact that he was severely injured against Miura, he continued to go on against him and ended up beaten to death.
Sha Dan YuanLin's brother. Played by Wong You-nam.
- Cassandra Truth: Played with. While many of the people he told believed him when he said he saw Ip and Liu fighting, his brother didn't.
- Tragic Keepsake: A kite made by his brother.
Chow Ching-ChuenA businessman who owns a cotton mill being plagued by Jin's bandits. His family flees to Hong Kong with Ip Man's family but he is shot in the head by a Japanese soldier. This causes him to forget his family and friends, thinking that everyone he sees is Japanese.
- Easy Amnesia: He is partially cured after hearing Ip Man beat Twister on the radio.
Jin ShanzhaoA martial artist master from the north who came to Fo-shan. Played by Louis Fan.
- Badass Longcoat: Justified; it's cold up north.
- Blood Knight - Though more to prove his name than out of pure bloodlust, mind.
- Defeat Means Friendship: Not in the first movie, mind you. But having the arrogance knocked out of him allowed him to find love and build a happy family by the second film, something he has come to thank Ip Man for.
- Doting Parent: Having an adorable little girl is yet another incentive to turn away from a life of violence.
- Easily Forgiven: He had been involved in Ip's life three times in the first movie: first he challenged him to a duel and accidentally smashed up his house (and attacked Ip with a sword), then he had become a bandit and tried to beat and rob the factory Ip was helping at. Finally, he gave Ip's location to the Japanese who were hunting him. Yet when he reappears in the sequel, he's greeted as an old friend.
- Handwraps of Awesome: in the beginning of the first movie, he has his right hand wrapped up. Appropriately, his style is much more brutal and powerful than anyone he faces... until he reaches Ip Man.
- Henpecked Husband: Even though he accuses Ip Man of being one in the first film, he becomes one himself in the second.
- Jerkass: In the first movie.
- Karma Houdini: See Easily Forgiven. He never pays for the various misdeeds of his youth.
- Love Redeems: "Thank you for knocking some sense into me all those years ago. Now that I'm married, I'm a responsible man with a family now!!"
- Smug Snake: Also in the first movie.
Li ZhaoA police inspector in Fo-Shan. When the Japanese occupied China, he became a translator for them. Played by Lam Ka-tung.
- Face–Heel Turn / Heel–Face Turn: Did the former when the Japanese invaded by becoming a translator to them. Then did the latter when he started to secretly work against them while still being the translator, his notable moment being to turn Colonel Sato's gun against him and kill him with it.
- The Quisling: Works rather closely with the Japanese Blood Knight Miura and Sato, however, subverted in that it's heavily implied he's doing it to protect his family.
General MiuraThe Japanese general in Fo-Shan who was also a martial arts enthusiast. He often took Chinese martial artists to his building to fight against their Japanese counterparts. Played by Hiroyuki Ikeuchi.
- Anti-Villain: He respects Chinese martial artists as brother warriors, and would rather have them be integrated into the Japanese Empire as such rather than killed as enemies.
- Authority Equals Asskicking: He turned out to be much more of a skilled martial artist then the other Japanese ones.
- Badass: Gave Ip more of a challenge than ten of his men.
- Blood Knight: He was driven by his desire to pit the Chinese martial artists with the Japanese ones.
- Big Bad: Of the first movie.
- Doesn't Like Guns: He forbids Sato from bringing a gun into his dojo, which he considers a place reserved for "martial spirit."
- Noble Demon: Despite being the antagonist, he threatened to kill Sato for shooting Liu in the arena. He was also baffled when Lin would rather die against him than surrender.
- Pirates Who Don't Do Anything: Spends his time practicing karate and fighting local martial artists rather than anything you'd expect a general to actually do during a war.
- Proud Warrior Race Guy: And an honorable one at that.
- Reasonable Authority Figure: Of an invading tyranny, yes, but he nevertheless treats the Chinese with as much dignity and respect as the Empire permits him to.
- Samurai: While nobody calls him this in the film, his dignified and noble behavior marks him as a likely descendent of a Warrior Clan.
Colonel SatoMiura's right hand man. He was the more sadistic of the two. Played by Shibuya Tenma.
- Colonel Badass: Averted. While Sato is a colonel, he's too much of a cowardly Smug Snake to be this.
- Karmic Death: He was shot by his own gun that he used to shoot Liu and Ip.
- Why Don't Ya Just Shoot Him?: He constantly tells Miura to just kill Ip.
Introduced in Ip Man 2
Wong LeungIp Man's first student in Hong Kong. Played by Huang Xiaoming.
- Defeat Means Friendship: Doubly subverted. At first he rejects Ip's offer to be the man's student and came back with friends for another round. When he's conclusively shown the error of his ways, though, he gladly accepts the tutelage.
Hung Lei-Nan (Master Hung)A Hung Ga master who started out as his enemy but later became his friend. Played by Sammo Hung.
- Acrofatic: A rather mild one but nonetheless he looked out of shape and yet managed to do acrobatic things to keep up with Ip.
- Handicapped Badass: Is able to fight Ip Man to a standstill in spite of being heavily afflicted with Asthma.
- Easily Forgiven: Introduced as the Opposing Sports Team who basically tried to keep Ip from starting a kung fu school and got Ip arrested for rescuing his prize student. This changes after they fight to a draw and he faces off against Twister.
- A Father to His Men: Master Hung's students are largely orphaned delinquents who are forced to turn to criminality to stay alive; by giving them a home along with his teachings, he gave them a second chance at life.
- Honor Before Reason: It is even lampshaded by Ip.
- Necessary Evil: He is something of a Jerkass and Opposing Sports Team to Ip Man early on, but it quickly becomes apparent that his rules, fees, and attitude are necessary for the martial arts schools to remain afloat under British rule.
- Opposing Sports Team: His initial role in the movie.
WallaceA chief police superintendent in Hong Kong who called in protection fees from martial arts schools. Played by Charles Mayer.
Taylor "The Twister" MilosA British boxer who came to fight in Hong Kong. Played by Darren Shahlavi.
- Arrogant Kung-Fu Guy: He's really smug and wants to show how good his boxing is compared to the Chinese.
- Ax-Crazy: Will happily kill his opponent if given an opportunity.
- Blood Knight: He decided to pick a fight with the Chinese for fun.
- Boxing Battler: In contrast with the kung fu the Chinese use, Twister sticks to boxing and manages to beat Hung Lei-Nang to death and hold his own against Ip.
- The Bully: He mocked Chinese performance and decides to crash their presentation for no other reason that he is a dick.
- Evil Brit: Has an imperialist mentality and suggest Chinese martial arts should stick to dancing.
- For the Evulz: Does what he does for the sheer joy of humiliating his opponents.
- Jerkass: He crash Chinese demonstration of their sports simply because he wanted to give them a real reason to scream (mocking their kiai).
- Lack of Empathy: Doesn't care he killed a man in a fight.
- Lightning Bruiser: The Twister can take and dish it out well while still being fast enough to keep up with Master Hung and Ip.
- Mean Character, Nice Actor: Darren Shahlavi himself was a gracious, well spoken and polite Kung Fu practitioner, a polar opposite of the monster that is Twister.
- Politically Incorrect Villain: He has a general distaste of Chinese martial arts and culture in general where he consistently mocked them.
- Put the "Laughter" in "Slaughter": Publicly and happily gloats that he's going to murder every Chinese warrior in Hong Kong in a rematch that is meant to clear his name.
- Red Baron: Twister
- Screw the Rules, I Have Connections!: See For the Evulz for more details.
- Villain with Good Publicity: Due to his connections, the British audience seem to think of him as just a popular, skilled boxer. Given the way they cheer for Ip Man's speech at the end this may no longer be the case.
"Fatso"A Chinese police officer in Hong Kong who ensures that the martial arts clubs comply with the British police. Played by Kent Cheng.
- Les Collaborateurs: Like Li in the first film, Fatso is a policeman who reluctantly collaborates with the foreign occupiers before turning against them and helping the Chinese.
- Foregone Conclusion: We all know what's going to happen to him...
Introduced in Ip Man 3
FrankAn unscrupulous American property developer who attempts to buy the school that Ip Man's son attends, thus putting him at odds with Ip. Played by Mike Tyson.
- Badass: Put it this way; when it's a challenge for the near-unbeatable hero of the trilogy just to survive a three-minute fight with you, you qualify for this trope.
- Big Bad: Probably the closest thing to one in the film, since he is the driving force behind most of the events that affect Ip.
- Boxing Battler: Almost exclusively uses boxing. Given that he's played by Mike Tyson, it's not much of a surprise.
- Combat Pragmatist: He is not dumb, if IP Man uses a stance that he can't punch with his boxing style he will just kick him so he stands up and then throw his hooks. He also wrestle better than Twister when Ip Man tries grappling him.
- Dramatic Dislocation: Ip uses his blocks to dislocate Frank's fist. It seems to work for a second, until he just relocates them and continues fighting as if it never happened.
- Noble Demon: When Ip Man goes the distance he honors his words and leave the school alone.
- No Sell: Several of Ip's attacks during the fight. While Ip Man is shown bleeding from the mouth during the fight, Frank rarely shows signs of damage. Whenever Ip does land a clean blow on him, Frank seems to only get stronger.
- Punched Across the Room: His punches hit so hard he throws Ip around like a ragdoll whenever a solid blow connects. Even if blocked.
- Scary Black Man: Again, not surprising, seeing as he's played by Mike Tyson.
- Soft Glass: Ip maneuvers towards several windows for him to hit if he misses Ip. Doing so doesn't even cause Frank to bleed.
- Time-Limit Boss: Ip only has to last three minutes to win (the equivalent of a single boxing round). It's one of the only fights in the series, that challenges if Ip could have clearly won if it lasted longer.