I haven't seen that one yet and honestly don't care enough to. Hey, maybe they'll finally go to space in Ip Man 5

2 is goofy but satisfying. A lot of arcs from the first film finish there, and the characters are very fun. The story is kinda silly but satisfying. The final fight with Ip Man and the British boxer is a fantastic payoff. The movie is packed with amazing action in general. The fight at the market, the duels with the other masters, Sammo Hung fighting the British boxer the first time. Excellent stuff.

Very radically different from the tone of the first film but I enjoy it a lot. It's the one I go back to more.

Ip Man 1 and 2 feel like they don't belong in the same universe, the tone is so different, and after 2 they get progressively goofier. It's also very clearly propaganda about how amazing China is over every other country.

However, the series works, because of Donnie Yen. Not just the action scenes, but he's a damn good actor. It's hard to make the audience care about someone who's basically a perfect person with no flaws but he's just so damn good.

The original Thomas Crown Affair from the 60s isn't amazing (though it is rather good) but it's Cool as hell. Steve McQueen and Faye Dunaway were the two coolest people in the world in that film.