Hello! First post here, so it might be a long one. I have a pretty long history with Spider-Man, and it really goes back to the 90's when I was 6 or 7 years old. I would watch the old animated tv-show as well as collecting the comic books. I remember when the first movie came out, and I had never been more excited for a movie. 12 years later and I'm still very much into superhero movies, but I would say Spider-Man will always be my favorite.
These last three days I decided to rewatch the whole Raimi trilogy. I hadn't seen them all in years, maybe not since the time around Spider-Man 3 coming out. Rewatching the movies, a wave of nostalgia as well as appreciation for these movies came over me. I forgot how much I loved these movies, and just how good they were. I even really enjoyed the third one, which I remember not being too warm on initially, but I guess hyperbole, time and internet makes you remember things differently. Anyhow, here's some of my thoughts on the movies:
Spider-Man
I would call this an excellent origin-story. One problem I have with many superhero movies is that the origin-movies often feel disjointed. The hero gets his powers and learns to use them, and then some random enemy shows up and that's that. What I like about this story is that Green Goblin is a very natural enemy to the story. You get to know Norman from Peter's perspective and he becomes a natural enemy within the movie. I feel like it flows quite nicely. Green Goblin is a great enemy for the first movie, even though a tiny bit of criticism for me personally would be the characterization of him, as well as the look of him. Norman in the comics was never really a nice person sucked into his creation, he was pretty power mad and a dangerous opponent even before he got his powers. But I can see why they would change him for the movie.
One popular topic has always been Kirsten Dunst as Mary Jane. There are people who really like her, and people who hates her. Me myself, I love her. I just think she fits perfectly, and the chemistry with Tobey is really nice. And that's one of the reasons why I think the Spider-Man movies worked so well. The emotional core with Peter wanting Mary Jane, but all these things getting in the way, it's a great story and Raimi knows how to tell it well. Action-wise I would say the first movie is probably the weakest out of the three. It's used appropriately and when needed, but when you break it down it's more a story about responsibility, love and growing up. A little bit of a missed opportunity that there wasn't more aerial fights between Spidey and Goblin, but this movie more than well stands on its own feet, and is a really good movie.
Spider-Man 2
The general fan favorite, and I will have to agree. I would say that this is the best paced movie in the trilogy, and in terms of structure I would call it perfect. Some people might argue about the lack of action in the first hour or so, but I give that a pass. Again, the emotional core really is the focus of the movie, and the action is a bonus. I just love how this movie plays out. Peter is having a really hard time balancing his two lives, and the movie asks a great question in terms of "Would you give up everything in your life to help others?", and it really leads to a compelling story. Performance-wise I think everyone brings it, and Alfred Molina gives the arguably strongest villain-performance in the trilogy. JK Simmons delivers a lot of gold in this one, probably his funniest performance out of the three.
It's hard to bring up any weak points, because for me it's almost perfect. It started to get a little cheesier, and I could live without scenes like the one on the train when everybody steps between Doctor Octopus and Spidey, with the notion that he has to go through them first. Raimi has a couple of scenes like that in all three movies, and I find them a little corny personally. What I love the most about the movie is the satisfying feeling it leaves you with. The first movie ending was a bit of a bummer, because you wanted Peter to get Mary Jane, and he didn't. This movie ends better, and after the hell he has to go through, he deserves that happy ending.
Spider-Man 3
I actually really enjoyed this last viewing, way more than I expected. I remember being slightly disappointed when it came out, but I guess it's easy to fall victim of internet hyperbole. I would say that this is actually a pretty good movie and a solid closer to the trilogy. I think there are problems, but for me, many of the problems are smaller ones. I've seen people say "It sucks because it has too many villains". To me, a movie with three villains COULD work. It could work, and it could be amazing. But the Raimi-movies where never ABOUT the villains. If you look at the first and the second, both Green Goblin and Doctor Octopus are obstacles that Peter face, but in the heart and soul, both movies are about Peter and his life, and how being Spider-Man affects it. So to me, the reason it doesn't work is because Raimi's movies are about the emotional core and not the villains themselves. When you have that in mind and you try to do it anyways with 3 villains, it's not gonna work.
I read some hate for Mary Jane in this movie, but I disagree. I think she acts quite rationally throughout the whole movie. In the beginning of the movie, Peter is kinda full of himself and quite the *****ebag. He's not very sensitive, and even if she doesn't share everything to him, he still comes off as very clumsy. Drawing parallels to him being Spider-Man is not the right way to go when he is trying to comfort her. I would also say the Gwen-kiss thing is clumsy, as well as most of the stuff he says at the restaurant. I think if you blame Mary Jane for the relationship leading to a break up, you must have been biased, because Peter deserves a lot of the blame.
One of my problems with SM3 is that the way they decided to go with the love story. After the ending of SM2 that left you with a warm feeling, with these characters finally getting each other, we get a movie when they fight and break up. Couldn't they just have been happy? For me personally, they should have left out the whole Gwen part, instead made Peter propose in the first half of the film, and maybe have ended it with the wedding or both of them still being very happy. Since more sequels were planned, I could see why they wouldn't use the wedding already, but I think it could have been a nice touch.
As for the enemies, I like them all separately, but in order to squeeze in all of them, you can tell that they suffer as a result. Harry getting revenge as a new Goblin, that story deserves its own movie. Venom and the symbiote, that deserves its own movie. Sandman, a lot could have been done there, in its own movie. The retcon with Sandman being the killer for Uncle Ben was quite silly and unnecessary imo. A few other negatives for me would be the Emo Peter Parker (which is just hilarious) as well as even more cheesy patriotism at the end. The newscaster-stuff doesn't bother me that much, but that ONE shot when Spidey runs in front of an american flag kinda does.
But lastly (and I want to finish, because this write-up is getting long), I do think the third one is much better than it gets credit for. It might still be the weakest out of the three, but I really liked it. For me it has the best action sequences of the three movies, it has the best Bruce Campbell cameo, and I think it has strong performances throughout. I was skeptical about Topher Grace, but I think he does a great job. Same goes for Thomas Haden Church as Sandman. And has Kirsten Dunst looked better as Mary Jane? Apart from being a cluster***** of a movie, the main negative impression that sticks with me after the movie is "too much of too little". I really loved many of the ideas they had with Sandman, I liked Harry wanting revenge, and I love Venom. So the problem for me is that by cramming too much into the same movie, none of these stories were as good as they could have been. Still, people calling this the "worst superhero movie", really? It has problems, and some pretty laughably bad stuff like Emo Peter Parker, but it also has redeeming qualities.
Anyhow, in case anyone read all of that, I applaud you. Just some thoughts after seeing the trilogy again.

And now I have a major crush on Kirsten Dunst again. She has the ultimate "girl next door" look.