#276. Mary Poppins (1964)
This is a childhood favorite that I wouldn’t necessarily seek out in adulthood, but is still a fond memory, as evidenced by another of those Simpsons spoofs that I treasure just about equally. Ah, who am I kidding? Julie Andrews was hot in this movie, and Dick Van Dyke is pretty classic.
#277. Fantasia (1940)
What Pixar is to the current generation, Disney (at least from the rental store) was to mine, and this is like an animated symphony, the kind of movie experience that it’s a little weird isn’t a little more ordinary, given that there are so many possibilities but most filmmakers tend toward expository. When you have a visual and audio experience possible, why do there have to be so many stories? I’m not against stories, but when a medium doesn’t necessarily have to be constrained by them, why force them on everything?
#278. Butch Cassidy and the Sundance Kid (1969)
This is a totally breakthrough Western, one that broke the John Wayne mold that had come to dominate the genre, operating more as a buddy flick, with Paul Newman and Robert Redford and “Raindrops Keep Falling on My Head” (I still can’t figure out why, exactly) and is probably responsible for every buddy film that followed (Crosby and Hope don’t count). If more filmmakers were to take inspiration from this, and not just for the buddy formula, we’d be better off.
#279. Three Kings (1999)
See? Here, George Clooney, Mark Wahlberg, and Ice Cube do a Gulf War version of Butch Cassidy, and we were all the better for it. Incredibly, this was another example of Clooney as bona fide movie star, but critics still weren’t having it. He had to wait pretty much a decade for the credit he richly deserved, and even then, it’s still dodgy. Critics are assholes.
#280. Rocky (1976)
The Rocky movies in general are something of a treasure. This is the only one on the list, but I recommend the whole series to posterity. There’s a line in Rocky Balboa (the sixth and most recent one) about persistence in the face of adversity, and that’s pretty much what these films are all about. There’s a lot more integrity to Sylvester Stallone’s opus (yeah, I’m saying it) than most people are willing to admit. So start here, and continue on with the rest of them.
#281. Easy Rider (1969)
This was one of those things that I knew (or thought I knew) by reputation for a long time, so when I finally did see it, I was pretty surprised. Peter Fonda is pretty much what you would expect, but Dennis Hopper, I really had to reevaluate everything I thought I knew. But Jack Nicholson steals this movie. That was the best discovery.
#282. The Adventures of Baron Munchausen (1989)
Here’s a cult Terry Gilliam flick that ought to be considered one of his defining masterpieces, rather than relegated behind the likes of the inferior Time Bandits and Fisher King. Here he finds a sufficient outfit to dress his usual predilection for oddity, much like Doctor Parnassus and Brazil. Also, Uma Thurman.
#283. Philadelphia (1993)
The only time icons Tom Hanks and Denzel Washington have worked together almost doesn’t really count, because Hanks is really too busy working with AIDS, the first of two Best Actor awards from the Oscars.
#284. Cold Mountain (2003)
Jack White! No, I’m kidding. It’s great to have him on the soundtrack, of course, but this is really all about the most interesting Civil War story no one else apparently ever thought about, as portrayed by Jude Law, Nicole Kidman, and Renee Zellweger.
#285. The Family Man (2000)
The actor who never gets any respect (okay, sometimes, but most of the time, when people are bitching about his style, it cancels those moments out) is Nicolas Cage. Movies like The Family Man ought to shut his critics up. When you’re the only actor who could play a role that way, that means you’re a pretty singular actor. That, in case you were wondering, means he’s special. In a good way.
#286. Wall Street (1987)
Charlie Sheen in the only role he’s really going to be remembered for (unless people actually start respecting Two and a Half Men in the future), what I may in the future be considering the prequel to its sequel, which I think might actually be the better film. But this one is pretty interesting, too. Oh, and I think someone named Michael Douglas is also in it. He may or may not play someone with a fairly famous name.
#287. Thelma and Louise (1991)
See? And without Butch Cassidy, you wouldn’t have this one, either. Geena Davis for a while had a career she deserved because of this movie. Brad Pitt owes his entire career to this movie. How often does that even happen, one of the medium’s biggest stars coming from something where he’s not even referenced in the title?
#288. Dude, Where’s My Car? (2000)
This is not even because I’m a huge fan of both Ashton Kutcher and Seann William Scott (not to mention Jennifer Garner), but because I absolutely believe this is a classic. Dude! Sweet!
#289. Natural Born Killers (1994)
Aside from everything else people have managed to talk about this movie over the years, there’s also Robert Downey, Jr. in a supporting role that steals the show, which is about the one thing all those people tend to overlook.
#290. A League of Their Own (1992)
I consider this to be Geena Davis, plus Tom Hanks warming up for Woody. A film that really needs to be rediscovered.
#291. Broken Lizard’s Club Dread (2003)
For pretty much everyone else, Broken Lizard is a comedy troupe that produced Super Troopers, and that’s pretty much it. I actually saw this one first, and even after I saw Super Troopers, I still ended up preferring Club Dread, almost entirely because of Coconut Pete. But the Broken Lizard players are pretty awesome, too.
#292. 10 Things I Hate About You (1999)
This was ostensibly a Heath Ledger vehicle, but the central figure in the movie is actually portrayed by Joseph Gordon-Levitt, the actor who gets to continue the legacy of Ledger, so that makes this one increasingly important, to see the two working together. Ledger clearly had some fun making this one, one of his earliest Hollywood performances, and closest to what he pictured for himself.
#293. True Romance (1993)
This is one of those cult flicks that I only somewhat recently had a chance to catch, and need to watch a few more times to truly catch up with, but it deserves a place on this list regardless.
#294. Top Gun (1986)
Sometimes an instant classic is an all-time classic, too, a box office blockbuster that truly stands up. You’ve got Tom Cruise and Val Kilmer, and a bunch of other stuff, “a need for speed,” and what else do you need?
#295. Blazing Saddles (1974)
My family became obsessed with Mel Brooks at one point (seeing most but not all of his films, including many that have become unfairly obscure, even though he’s generally much better than critics are willing to concede), and this is a classic by any regard. Gene Wilder at one point actually had a career, and this is the movie to thank for that.
#296. True Grit (1969)
It’s funny, because the recent new adaptation made it clear just how long ago and fuzzy my experience with this one actually is, because I remember very little, but it was a John Wayne standout then, and it’s a John Wayne standout now. Wayne, I should explain, is my dad’s favorite actor, so my childhood was a mix of Disney and Westerns. Now it’s easy to assume most of the Westerns were in fact Disney movies, because they might as well have been. Just sayin’.
#297. Trading Places (1983)
Saturday Night Live has a long history of providing Hollywood with new stars, and this is one of those weird confluences where two of those stars actually aligned from different eras of the show. They were, of course, Dan Ackroyd and Eddie Murphy. I would love if they did a follow-up to Trading Places, actually. Except now, both of them would be trading up.
#298. Road Trip (2000)
There are other things to love about this movie (the creepy/cool DJ Qualls, for instance), but this is otherwise known as the one time Tom Green was unabashedly entertaining.
#299. Heaven and Earth (1993)
The awesome thing about Oliver Stone is that where other filmmakers are content to touch on subjects and then movie on, he tends to meditate a bit longer. It’s more than safe to say that he’s the Vietnam War’s Spielberg, at the very least. Here he tries to help Tommy Lee Jones find some piece. Ha! And it turns out okay for everyone!
#300. Grumpy Old Men (1993)
This is another of those movies that might as well be a prequel to its sequel, nice to see in order to find out how Matthau and Lemmon ended up as retirement age chick magnets in the first place.