Now that all three films are out, it’s impossible to leave any of them behind—or to avoid comparing them. They all explore the life of the same man: a legendary martial arts master whose story is emotionally compelling and, let’s be honest, incredibly fascinating.
The Ip Man trilogy is inspired by the life of Yip Man, the renowned Wing Chun master who became internationally famous for spreading this form of Kung Fu and for being Bruce Lee’s teacher. While all three films focus on the same historical figure, each approaches his life from a different angle.
Why the Change in Actor Makes Sense
Some fans prefer the first two films because of the actor, Donnie Yen, but I’d argue that the third film makes a smart and respectful choice by casting Anthony Wong. The story follows Ip Man in his later years, and instead of using makeup or digital aging (which often lacks realism), switching actors was a more honest and effective decision.
Let’s break down each film and why they’re all absolutely worth watching.
Ip Man (2008): A Hero Emerges During War
The first film begins in Foshan during the 1930s Japanese invasion. In this southern Chinese town, martial arts schools are everywhere, and masters constantly compete to establish their dominance. But Ip Man doesn’t need to prove anything—he’s naturally revered, even though he tries to avoid unnecessary fights.
He’s a calm, peaceful man with a strong-willed wife and a quiet domestic life, often interrupted by friendly sparring and late-night Wing Chun practice with friends. But that peaceful life quickly ends when the Japanese army arrives, stripping people of their rights and property.
Driven into poverty, the townspeople must choose between survival and submission. Eventually, Ip Man rises to defend his community, taking on the role of protector and unifier. His strength, philosophy, and calm demeanor make him a reluctant yet perfect leader.
The film is not just a martial arts showcase—it also explores themes of dignity, resilience, and justice under oppression. It’s a powerful start to the trilogy and arguably the strongest installment.
Ip Man 2: Legend of the Grandmaster (2010): A Flawed but Impressive Sequel
Set nearly two decades later in 1949 Hong Kong, the second movie takes us into a city now under British colonial rule. As usual, martial arts reign supreme—but this time, the system is corrupt, with foreign powers charging masters to legally run their schools.
Ip Man relocates to Hong Kong to start a Wing Chun academy, simply to feed his family. To do that, he must first defeat the other local masters in combat. He does this with dignity, but things escalate when a foreign boxing champion challenges the Chinese fighters, creating a tension-filled showdown.
While the action is still excellent—especially the fight at the fish market and Ip Man’s duel with Hung Chun Nam, played by legend Sammo Hung—the film suffers from weak performances by foreign actors and exaggerated stereotypes. The British characters are cartoonish villains, and that undermines the story’s emotional weight.
Also worth noting: the real Ip Man never fought a British boxer. That part is fictionalized, and in real life, his fights were brief and far less dramatic. Still, despite a disappointing final act, the movie delivers great choreography and some important themes around cultural resistance.
Ip Man 3: The Legend is Born (2013): The Final Chapter
In the third installment, Donnie Yen steps away, and Anthony Wong takes over as the aging master returning to postwar Hong Kong. This final film has a melancholic tone, told from the perspective of Ip Man’s son, Ip Chun.
The style and pacing reflect the character’s later years—quiet, thoughtful, and calm on the surface, yet with the same unwavering strength underneath. Of course, no Ip Man film is complete without a final showdown, and this one delivers what I think is the best fight of the trilogy. Not just because of Ip Man’s performance, but because of how his disciples also rise to the occasion. The emotion, setting, and choreography all align for a truly memorable scene.
It’s a graceful ending to a story of humility, strength, and legacy.
Final Thoughts: Which Ip Man Movie Is the Best?
If I had to choose a favorite, it would be the first film. If I had to pick one fight, it would be the last one in the third film. Together, they form a cohesive and powerful trilogy that tells a complete story—not just of a martial artist, but of a man of principle.
Of course, the world of Ip Man doesn’t end here. I’m still planning to watch The Grandmaster (2013), because when it comes to learning about this fascinating character, it’s never enough.
Highly recommended for martial arts fans, history lovers, and anyone interested in stories of quiet strength and resistance.