The Joker
The Clown Prince of Crime
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Wow, Cliche Rhino ended an entire film franchise and now apparently a really good thread too? Sheesh. Just wanted to throw in a quick 'n' dirty very preliminary thought about these movies in.
The Raimi movies will always hold a special spot in my heart. I'm younger than probably a majority of the people who post in this thread, and was first introduced to Spidey by the 90s animated series, the early PS1 games, and then these movies. I didn't pick up a comic book until much later (Ultimate Spider-Man Ultimate Collection Hardback Vol. 1 at Books a Million--fell in love) and it wasn't until much more recently that I started picking up single issues (aside from a promotion Marvel ran right before Civil War in the mid-00s where they placed reprints of the first 20-or-so Stan & Steve classic issues in a local paper--loved those things!).
While I always loved watching the cartoon and it really captured my imagination, six-year-old me was STOKED when I first saw Spider-Man. It all seemed so real. I was sucked in, never to escape. The lore was so rich, the world so lived in, the characters so relatable and fleshed-out. Tobey Maguire WAS Spider-Man (although, even a preteen ItchyWebShooter didn't believe Tobey Maguire was in high school)!
I could wax nostalgia about these films all day--my dad and siblings and I used to sleep in the living room, eat ice cream, and watch Spider-Man whenever my mom was out of town. Spider-Man 2 is the first movie I ever remember being so excited to go see, and so awed and thrilled walking out of the theater. And even as Spider-Man 3 brought a close to my favorite film trilogy of all time, it sort of served as a close to my childhood--a chapter in my life.
These films were my favorite because I grew up watching them and Spider-Man was my favorite fictional character. These things remain true to this day. But as I've gotten older and started appreciating more of the technique and nuance of film and filmmaking, I've realized just what great examples of superhero cinema these films are--especially at the time they were released! Sam Raimi had a way with tracking shots, unique POVs, and a real sense of location in his scenes. There was never a boring shot in this series. And even as some of the CGI effects have become dated, 90% of the effects in these movies look as realistic as some of the big-budget blockbusters being released today. I'm sure that is in large part due to Raimi's affinity for using practical effects when possible, something I will never stop loving and respecting him for.
I'll never quite be able to fully divorce my feelings for these films from the memories I have of the joy they brought me--watching with friends, eagerly anticipating 3 with one of my closest friends to this day, playing all the video game tie-ins with many friends, etc.--so I'll never be completely impartial, but as distanced as I can get myself from all that; my feelings about these movies shift only marginally. I still enjoy the heck out of them, and I believe that I would if I'd just seen them for the first time a few weeks back.
Of course nothing is perfect. There are flaws in each of these, the most visible appearing in the much-derided Spider-Man 3, but there's a true sense of energy, of love for the characters pulsating throughout each--and I think that's what continues (and will continue) to separate them from such trite money-grabs as X3, Ghost Rider, and many other of its contemporaries. I can't remember who said it (it may have been Peter Travers, or perhaps Roger Ebert--and I'm paraphrasing) but the statement "There is a heartbeat under the action and drama" has never rung truer. I believe that's why MCU films have been so successful, and I hope the success continues with a great new Spidey film next summer. But Raimi's masterpieces--the Spider-Man trilogy--will always hold a special spot in my heart (and obviously millions of others). Regardless of what some snobs and nitpickers think, I believe it's very obvious that the man had a true and genuine love for the character and his mythos and that he gave us what he believed was the best version he could do on film. These movies will always be some of my favorites and will live on as my favorite film trilogy ever indefinitely!
Nice post. Welcome aboard

I'd put it in the top 5, probably top 2 alongside TDK.
Ditto. It's #2 after TDK for me. Even Kevin Fiege said he considers it one of the best superhero movies ever, and that's the standard they have to live up to for Spider-Man Homecoming.