1. Batman: The Movie (1966)
If you're some cynical cynic from Cynicstown, maybe you don't realize how great this movie is. But this flick is brilliant. It perfectly captures one particular side of comics and superheroes and mines that side with abandon. And it has staying power. Look at it this way: I was born in '85 and this movie was a staple of my childhood, and the childhoods of lots of my friends. Adam West kills it as the Bats. At least until 1989, this was the definitive version of Batman in the public consciousness, and it's still sort of the quintessential example of what most people think of when they think "comic books" (for good and ill). Love it.
2. Batman Begins (2005)
A, um, slightly different take on Batman than the previous entry. While Batman: The Movie tapped into the campy good-nature of Batman (and so much of the Silver Age), this one is really all about The Dark Knight. All seriousness and brooding, but snappier than the 1989 Tim Burton effort (which hasn't aged well, sadly). Christian Bale heads a pretty star-studded cast and everyone puts in performances which really inhabit the characters. This isn't the only way to do Batman, but it's a compelling one and a tone which is informed by some of the great work on Batman done in the 80s (in comics) and the 90s (on television).
3. The Dark Knight (2008)
The sequel to Batman Begins, continues this totally engrossing take on Bats with the addition of an anarchic (and highly praised and praiseworthy) Joker. Drawing heavily from beloved comic sources like The Killing Joke and The Long Halloween, this film was (deservedly) a massive hit. It'll be interesting to see where the franchise goes from here.
4. Superman: The Movie (1978)
Like the classic Batman flick from '66, this Supes movie was a cornerstone of my childhood (and many others my age). Christopher Reeve is Superman for so many people from across several generations. This film actually holds up really well, presenting a mix of taking-the-content-seriously and charming good-naturedness which is often missing from superhero flicks these days. This one had a star-studded cast too, with Gene Hackman as Lex Luthor, Margot Kidder as Lois Lane and Marlon Brando as Jor-El. Unlike Batman, which has had a few successful live action iterations, Superman has never really again been presented outside of the template set forth by this film.
5. Superman II (1980)
2008 was a great year for superhero films, it seems. Robert Downey, Jr. is Tony Stark in this one, inhabiting the character perfectly. An essentially pitch-perfect film adaptation, this captures the playboy fun and adventure that can make the character so great. Plenty of nerd-bait, like the creation of S.H.I.E.L.D., and an excellent cameo at the end of the credits makes this a memorable entry.
10. Watchmen (2009)
A near-perfect adaptation of one of the greatest graphic novels of all-time. The great deconstruction of the superhero makes it to the big screen with much success.
Runner-Up: Spider-Man 2 (2004)
While the first Spider-Man film in the franchise was pretty good, it felt a bit flat. Here, the pace is brisker and the story better. I'm not a hardcore Spidey fan so I miss a lot of the fan gripes with this franchise, but I thought this was a highly enjoyable film and easily the best of the the three films made. I just don't dip into this franchise quite regularly enough for it to make my top 10.
The Guilty Pleasure: Teenage Mutant Ninja Turtles (1990)
I was 5 when this came out, loved the cartoon, and so this was right in my wheelhouse. It actually does a reasonably admirable job striking a balance between the darker source comics and the, well, cartoonish kids cartoon. It's definitely trashy, but it's oddly satisfying and certainly hits my nostalgia buttons in the right spots.
Final Thoughts: Okay, if it wasn't obvious while reading the list, I'll admit that I'm clearly primarily a DC comics fan. The lone Marvel title in the top 10 probably gave it away. Other titles that some folks might include in their lists (The Hulk [Hell, I preferred the Ang Lee version to the newest one], Daredevil, X-Men) just don't resonate with me as much. I'm not making any claims about this list other than it's my Top 10 personal favorites. I wouldn't hesitate in recommending any of these movies, but I wouldn't make any claims about them becoming your favorites or nuthin.
This is also a list I created off the top of my head, so I may be forgetting something really good.
The other thing is: this list is clearly dominated by recent titles. If I had to expand this list out to 15 or 20 titles, nearly all the rest of the films would be pretty recent ones too. Off the top of my head, I can think of a couple reasons for this: 1) there's been a definite adaptation renaissance in the last decade or so - more comic book titles (superhero and otherwise) are getting adapted to film than ever before, 2) I think the nature of superheroes and comics lend themselves to being "of their time" in a way that makes them particularly susceptible to aging poorly. Will all these flicks in my list last the test of time? Unlikely. I think Tim Burton's 1989 Batman film provides a good case study. Heaped with praise on release (I loved it as a kid), it helped redefine what a "comic book movie" could be to the general public and finally supplanted the Adam West Batman as the definitive one in the public imagination. But, well, I rewatched it recently and it comes off as pretty hacky and dull, without a lot of the charm of that 1966 version. Ten years on, and it felt like the "superhero genre" had left it in the dust.
All this said, I guess it's time to go watch my extended edition of Ghost Rider. *cough*