Ip Man/Characters

Ip Man (Master Ip)
The titular character. Ip is a Wing Chung master whose house was seized by the Japanese. Played by Donnie Yen.
 * Awesome Yet Practical: The fundaments of Wing Chun Kung Fu.
 * Badass
 * Badass Long Robe
 * Berserk Button: Will NOT stand down when defending the Honor of Chinese Warrior Culture.
 * Beware the Nice Ones
 * 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?"
 * Estrogen Brigade Bait
 * The Fettered
 * The Hero
 * Historical Domain Character: Of Yip Man, Bruce Lee's master.
 * Honor Before Reason
 * Hot Dad
 * 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.
 * Martial Pacifist
 * The McCoy
 * The Messiah
 * Misery Builds Character: And makes you a more loving father.
 * Nice Guy
 * Not So Stoic: He was often calm and collected but he finally loses it when he saw
 * 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: Albeit a sweet and kind-hearted example.
 * Rags to Riches: Inverted. He started out a rich man, then was forced to live in abject poverty when the Japanese occupied Fo-Shan.
 * Rapid-Fire Fisticuffs
 * 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.
 * Showy Invincible Hero: While he always curb-stomps his opponents, at least in the first film, he did it with such a style.
 * Smoking Is Cool: When he is at ease.
 * Tranquil Fury
 * Warrior Poet
 * Warrior Therapist

Cheung Wing-sing
Ip 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.
 * Yamato Nadeshiko

Master Liu
A martial artist teacher who had a friendly fight with Ip. Played by Chen Zhihui.
 * Overshadowed by Awesome
 * Proud Warrior Race Guy
 * 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" Lin
Ip's friend who runs a teashop. Played by Xing Yu.
 * Hot-Blooded: Deconstructed; his passionate hate against the Japanese ended up getting him
 * 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 Yuan
Lin's brother. Played by Wong You-nam.
 * Annoying Younger Sibling
 * 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:

Chow Ching-Chuen
A 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 cured after hearing Ip Man beat Twister on the radio.
 * 'Tis Only a Bullet in the Brain

Jin Shanzhao
A martial artist master from the north who came to Fo-shan. Played by Louis Fan.
 * Arrogant Kung Fu Guy
 * 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.
 * Heel Face Turn
 * Henpecked Husband: Even though he accuses Ip Man of being one in the first film, he becomes one himself in the second.
 * Hey, It's That Guy!: Yup, that's the same super-strong boy who literally punched his way out of prison in Riki-Oh: The Story of Ricky 17 years ago...
 * Jerkass: In the first movie.
 * 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!!"
 * Proud Warrior Race Guy
 * Smug Snake: Also in the first movie.

Li Zhao
A 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
 * Les Collaborateurs
 * Reverse Mole

General Miura
The 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
 * Badass in Charge
 * Four-Star Badass
 * Blood Knight: He was driven by his desire to pit the Chinese martial artists with the Japanese ones.
 * Big Bad
 * Doesn't Like Guns: He forbids Sato from bringing a gun into his dojo, which he considers a place reserved for "martial spirit."
 * Honor Before Reason
 * 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 Sato
Miura'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.
 * Complete Monster: In contrast to Miura.
 * The Dragon
 * Smug Snake
 * Why Don't Ya Just Shoot Him: He constantly tells Miura to just kill Ip.
 * Why Don't Ya Just Shoot Him: He constantly tells Miura to just kill Ip.

Wong Leung
Ip 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.
 * Hot-Blooded

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.
 * Badass
 * Badass Grandpa
 * Handicapped Badass: Is able to fight Ip Man to a standstill in spite of being heavily afflicted with Asthma.
 * Heroic Sacrifice
 * Honor Before Reason: It is even Lampshaded by Ip.
 * Old Master
 * Proud Warrior Race Guy

Wallace
A chief police superintendent in Hong Kong who called in protection fees from martial arts schools. Played by Charles Mayer.
 * Corrupt Cop
 * Evil Brit

Taylor "The Twister" Milos
A British boxer who came to fight in Hong Kong. Played by Darren Shahlavi.
 * Arrogant Boxing Guy
 * Ax Crazy: Will kill his opponent for the sexual pleasure of it first chance he gets.
 * Big Bad: Of Movie 2.
 * Blood Knight: More to indulge in his sadism and bloodlust than actual love for combat, though.
 * Complete Monster: The single most honest and realistic portrayal of an Asian-hater ever put to screen.
 * Evil Brit
 * Evil Counterpart: The exact opposite of Ip Man.
 * For the Evulz: Publically humiliates Chinese Martial arts and gleefully beats sick and elderly Chinese Warriors to death for the sexual-pleasure derived from both because the British government has got his back covered.
 * Good Old Fisticuffs: In contrast with the kung fu the Chinese use, Twister sticks to boxing and manages to  and hold his own against Ip.
 * Interplay of Sex and Violence: He clearly gains intense sexual pleasure from bullying and murdering Chinese Warriors.
 * It's All About Me
 * Jerkass
 * Karma Houdini: Doesn't die, or even get crippled, for murdering Master Hung Lei-Nang.
 * Lack of Empathy
 * Lightning Bruiser: The Twister can take and dish it out well while still being fast enough to keep up with Master Hung and Ip.
 * 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: Publically 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
 * Sex Is Violence
 * The Sociopath
 * Screw the Rules, I Have Connections: See For the Evulz for more details.

"Fatso"
A Chinese police officer in Hong Kong who ensures that the martial arts clubs comply with the British police. Played by Kent Cheng.
 * Only Known by Their Nickname
 * 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.
 * Reverse Mole

Bruce Lee
A young kid who wants to be (and will be) Ip Man's student. Played by Jiang Daiyan.
 * Foregone Conclusion: We all know what's going to happen to him...
 * Mouthy Kid