Or eighteen. Basically, second-half of high school. At least, that's when I saw these movies, and they made an indelible impression on my life.
There are a few factors at work here - first, all of these movies are totally accessible to anyone who's grown up watching movies. Nothing too eclectic, nothing too off-the-beaten path. Second, all of these have valuable life lessons for anyone making the transition from young punk to adult (and trust me, not everyone makes this transition). Everything from girls to school to responsibility...it's all here. And lessons aside, they're damn slick, enjoyable movies to watch.
Eyes Wide Shut - Okay, this is pushing the "mainstream" requirement a little (it is a pretty good thriller for a bit there...and there are a LOT of boobs), but if you're willing to roll with it, the film is here for you. Basically, when I saw this the summer before my Senior year of high school, it blew my head apart. I had no idea women thought this much about sex and had the same desires and fantasies my Catholic-raised ass was struggling with. Of course, the next year I would go to college and find out (alas, not through direct experience) that girls are even more obsessed with sex than guys (some, anyway), but for the time being, this was...very valuable.
Oh, and anyone who says this is "lesser Kubrick" can shove it. This and Barry Lyndon for the win.
A Clockwork Orange - Hey, two Kubrick movies! Hey, boobs aside, they really couldn't be any more different. Another movie that, when I saw it the first time (in a theater, what what)...well, it was one of those movies I saw and couldn't believe it existed. I had a vague notion that something like this could exist, but...wow. The lesson here is basically to question authority. That's something no respectable 17-year-old has ANY problem with, but I'll also say that for the most part, guys enjoy this movie a lot more when they're younger than when they're older. I mean, I'm only 23, and I still think it's a fine film, but I don't think half as well of it now as I did then.
Chasing Amy - Near and dear for a lot of men, for a reason. Young men, take notice - the girl you're crazy about was around before you, and there's a good chance there'll be an "after you" too. Don't get hung up on it. Try to trust her, especially if she says she loves you. If you get burned, you get burned, that's life. But don't get all jealous about stuff that has no bearing on you. I'm still learning the damn lesson Holden learned in this film, but I'm glad as hell that I had a few years' head start on it.
Fight Club - YeeeeAAAAHHHH. Like A Clockwork Orange, I don't like it half as well as I did when I was 17, but I fucking LOVED this movie when I was 17. Sure, I didn't catch onto the biting social commentary that was underneath the surface (that is to say, don't get caught up in ANY cult, be it mainstream corporate environment or anti-establishment underground), but everything that's on the surface (that is, everything that Tyler spouts in the pre-terrorism section of the film) is stuff genuinely worth considering whether or not you end up agreeing with it. Again, like A Clockwork Orange, it gets you thinking about stuff you might not have before, and is damned entertaining while it does it.
Clerks - More Kevin Smith! A little repetitive, maybe, but Kevin Smith is a guy who appeals pretty directly to young men. Certainly did to me. Anyway, two major things here: a) recognize a good lady when you land one, and don't keep chasing after what you think is your dream girl, because she probably isn't, and b) work a job you don't mind working. It doesn't have to be your dream job or your career, but really look around and find something you're comfortable with. It's not worth minimum wage to hate your life for up to eight hours a day (unless that's REALLY all you can find).
Dazed and Confused - And dude, just enjoy it. It's high school. Even if they don't end up being the best years of your life, there are so many opportunities to have so much fun. Soak it up. It's the last years you'll be given a roof over your head and food on your plate. Don't worry about the future, just do the best you can and find things you enjoy doing.
Bonus Religious Pick: The Last Temptation of Christ - Okay, if you're any denomination of Christian, get your ass out and see this movie. First, it's a good barometer to determine if you understand the concept of art, and second, it forces you to reconsider your idea of Jesus. I was raised non-denominational Christian and went to Catholic school for all of my formative years, and this was really powerful stuff. Don't let anyone tell you The Passion of the Christ is a better portrait, either.
My girlfriend has some thoughts on movies to recommend to high school age girls. Blog tie-in...ACTIVATE!