There are four main movies in the series, though you could say there are five if you count a spin-off that came about between the third and fourth movies, focusing on a side character from the third. Also, despite the fourth movie in the main series being labeled as “The Finale,” there has been talk of an coming out at some point, but time will tell whether that comes to fruition. Anyway, for now, all the main movies in the series were directed by and starred in the titular role.

was a real person who’s best known for popularizing the martial arts style known as Wing Chun. The films dramatize elements of his real life to some degree, but take certain historical liberties in order to remain exciting and simultaneously function as martial arts/action movies. The films are all ranked below, including that aforementioned spin-off. All , but the best in the series combine that stuff with well-told dramatic stories. All are worth checking out if you're into martial arts cinema, but some are arguably more essential to the genre than others.

It’s ranked last here, sure, but does still have some scenes of Donnie Yen kicking ass, and if a movie has that, it can’t be considered worthless. It is the least compelling of the Ip Man movies, though, because the quality of the action takes a dip here to some extent following the first two films, and the story’s a little muddled. The titular character stands up to some gangsters here, and uses his martial arts skills to stop them from collaborating with a malicious property developer to take control of a large area.

The most noteworthy thing here is probably also the most bizarre part of Ip Man 3: the fact that , of all people, has a supporting role here. It’s stunt-casting that gives the film a little more of a pulse, but otherwise, this is disappointingly standard and overly familiar stuff as far as martial arts movies go. And, sure, plenty of martial arts movies have featured ordinary stories bolstered by great action, but the fight sequences here aren’t quite up to the high standards of the rest of the series. , albeit a tiny bit disappointing overall.

2019 saw the release of two pretty major films that both had actors playing the legendary . played him in one of the more controversial parts of , while Lee was featured more prominently in , being played by there. And there was good reason for this: Bruce Lee is the most famous student Ip Man ever had, and ended up having a short but essential career as a leading actor in a handful of classic martial arts movies.

When Ip Man 4: The Finale slows down at times, you might well find yourself wishing you were watching an actual Bruce Lee film, but then it’s easy to forgive the slower moments when Ip Man 4: The Finale gets flashy and action-packed. It also doesn’t overuse Bruce Lee. It’s if it does end up really being “The Finale.” Parts of this prove emotional, and the better dramatic moments end up being compelling for vastly different reasons than the action sequences being entertaining.

Cheung Tin-chi first showed up in Ip Man 3, and was someone who lost (only just) a fight to Ip Man, which makes him reconsider whether he wants to continue pursuing martial arts. That’s where this 2018 spin-off, , picks up, and though it’s certainly got some imperfections, it’s better than you'd expect it to be. Honestly, it’s more interesting, dramatic, and stylish than Ip Man 3, and probably has slightly better action on top of a better story, too.

was the director here, and though he’s quite an accomplished filmmaker, he’s probably best known for being an action choreographer, with his work seen in movies like , , and . The fight scenes in Master Z: Ip Man Legacy scratch a similar itch to some of the action Woo-Ping’s famous for compared to the other Ip Man movies. But it’s a spin-off, so it doing its own thing feels justified. Also, popping up in a martial arts film is generally a good time, and is also surprisingly good here in a villainous role.

Kicking off the series in 2008, the original Ip Man works as a very good biographical film that explodes into action when it needs to, and thoroughly satisfies and impresses in that department, too. It’s still a dramatization, but it does at least feel the most grounded out of any movie in the series, following him during the events of the Second Sino-Japanese War. Some liberties are taken, but it’s nonetheless a period drama with martial arts action, and does reflect Ip Man as a person, and the values he was known for upholding.

It's a dark film at times, but ultimately has a certain inspiring quality, thanks to the central story here involving standing up for what one believes in. The titular character perseveres during a dark time in history, and does only resort to violence when the situation really calls for it, perhaps being less aggressive than protagonists might otherwise be in most martial arts movies. Ip Man is somewhat restrained, but it also doesn’t disappoint when it comes to action, and it .

A very strong sequel that might well be even better than Ip Man, impresses more as an action movie than the first film did, all the while (admittedly) taking things in a slightly looser direction as far as history is concerned. The story here takes place after World War II, and the premise pits Ip Man against various opponents, all of whom have heard about his mastery of Wing Chun and wish to challenge him, be it through official matches or other means.

When the combat is structured, Ip Man 2 isn't too intense, but once the stakes are raised and things get more dangerous, Ip Man 2 does inevitably get grander and more dramatic. , and having Sammo Hung show up in a supporting role certainly doesn’t hurt. The fight sequences are continually impactful here, and the story is simple and efficiently told. It’s just very satisfying for a martial arts film, and can count itself as one of the best released during the 2010s.

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