I've seen seven of his films. It's kind of hard to rank them for me. He's an interesting director, he makes bold and unique films and I liked everything I've seen from him so far, but I can't say I truly LOVE any of his films yet. I don't really know why that's the case, because they're mostly all very clever and well made films and I do feel like I understand why some people are huge fans of his films. I personally find myself enjoying them, but I can't call any of them true favorites yet. It's impossible for me to rank his films, but I'll give a short commentary on every film I've seen from him so far:
Videodrome
Weird, little horror film that tackles the more detrimental aspects of media in a classic Cronenberg-like fashion! I like it. It's a deliciously f*cked up film.
The Fly
Possibly my favorite Cronenberg experience yet. It's horror at its most effective and it treats every single one of its characters with a great deal of respect (even the monster), which I really appreciated. My favorite scene is the "birth scene". Horror at its finest.
I'm not completely sure if the film would have the same effect on me during a rewatch, but it was able to completely captivate me during my first viewing of it in every possible way, so I guess I'd consider this my favorite film of his, for now.
Dead Ringers
A psychologically complex story about two twin brothers who're both famous doctors. It's weird, it's shocking and it's masterfully made, but sometimes I do think Cronenberg's fascination with the "extreme" gets in the way here of what could have been an even more profound and better movie. That's my opinion, though. I think it's a great film, but I don't think it's the masterpiece that some people make it out to be. I feel like the desire to shock took over in the end and reduced the story's resonance a little bit.
It's still one of Cronenberg's most ambitious films and I can definitely see why so many people call it a masterpiece. Jeremy Irons' performances are also incredible!
Crash
A very bold films about the search for emotional satisfaction through extreme experiences. I came to appreciate it more since my first viewing, but I wished it would focus a little bit more in depth on the mentality of its characters, in stead of repetitiously showing the shocking stuff that is the result of that mentality.
eXistenZ
This is a very enjoyable adventurous sci-fi film that contains most of Cronenberg's classic (gory and horror-like) features. Yep, I like this one.
A History of Violence
It's a neo-noir story that strongly focuses on the theme of violence. The difference between this film and other films of its genre is how much weight, attention and psychological consequences every single act of violence has in this film. The film is pretty good in those terms, but to me it feels a bit too particularly limited to its theme of violence to be something truly great or profound. That's why I don't LOVE it as much as many other people do.
Eastern Promises
A good film about the criminal underworld and its filthy consequences and about the people who are trying to undermine the existence of it through extreme sacrificices. I like this film, it's well directed and it has a couple of great scenes, but ultimately it's not that profound or refreshing content-wise as it appears to be. Still a cool watch.