I first saw this movie when it came out in the theaters and I was a teenager myself, and I remember feeling a just a little shortchanged and even dirty, like I'd been manipulated in a way. I did enjoy it, but the reasons for enjoying it do not hold up today. Watching it again has been fun because looking at it through adult eyes, I am having fun seeing how easy it is to spot the dated qualities and outmoded philosophies that, as one reviewer said, were pretty much defunct by 2000, or maybe even by 1995-6.
And it's not like I was some profound kid who had all this insight how mass media sells these ideas to young people...I bought into the whole "Seattle grunge" thing lock, stock and barrel, I thought guys with stringy unwashed hair and bad attitudes were totally hot, I wore crocheted vests, mood rings, and colored sunglasses with the best of them. So me thinking that something did not ring true must have been because it is pretty obvious that this movie is in essence a failure.
1. The characters-The movie works really hard to make Troy be the better option for Leilana. For teenagers, he was totally sexy to watch on screen and totally swoon worthy, but his utterly obnoxious attitude, his rudeness to Ben Stiller's character, and his bullying just came off as unpleasant at the least, and his philosophy for not working are textbook definitions of a narcissist. Hearing some of his pseudo intellectual discussions are painful and embarrassing, because it is clear that the movie feels that young Gen X'ers embrace and admire such outlooks unequivocally and at face value. And kids were supposed to identify with this person? What an inconsiderate person, to stand up Leilana's father for the job interview and lead her to blame herself, and to embarrass women around him for being attracted to him. Any good friend and countless therapists would advise against having him as a boyfriend. The sad few seconds devoted to his dying father are not enough to redeem him or "understand" him.
Bottom line, if Ethan Hawke was supposed to make this person somewhat sympathetic, he failed, or if he truly was supposed to be this unlikable, then good work.
Leilana did come off as sympathetic and overall was well played by Winona, and her beauty is the one of the few things in this movie with true staying power. Her character does some pretty awful things, though. When her boss rudely rebuffs her video ideas, she humiliates him on air. When her friend offers her a job, she snaps at her. Instead of swallowing her pride and working at the gap for a bit, she resorts to the embarrassing "gas card" scene, which we are supposed to think is cute and rebellious. It is totally unconvincing that a "valedictorian" would ever be so irresponsible and immature, even if she had fallen on bad times.
As for the other two, they are both well acted and likable, but seem to be added on simply to achieve a gritty "90's" edge, like HIV testing and coming out to your parents. Neither subplot is developed enough to give this movie the edge it craves. Both are attractive and funny, and Vicky especially projects a friendliness, sympathy, and is cute as hell in those throwback clothes.
2. The Michael stuff really is a failure. Ben Stiller did a good job acting in this movie and came across as warm and real, but this movie is his work too. I guess a simple plot device would have been to make him more arrogant from the get-go so that he could seem like the "bad guy" but that would have been cheap. Either way, the movie does seem like it's trying to convince you that he either "betrays" Leilana or "doesn't understand her" the way Troy does, and it doesn't work. Those two had a positive chemistry and seemed to complement each other as characters. To make this a true coming of age and growing up story, Leilana should have either chosen Michael, who emphasizes growing up, taking responsibility for your actions, and change for the better, or decided to be on her own for a while to become a more mature person.
3. The biggest failure of this movie, and in my opinion, the most dangerous, is how it elevates Troy's attitude as the noble one above all, as if being narcissistic and self-involved are desirable. Being that he is the hot guy of the movie and that the other characters seem to respond so positively to him, a young teenager is left with the message that this is the "new" way to be and that Michael's responsible and kind persona are "hypocritical" or "selling out." Leaving the theater back in '94, I was enjoying myself thinking about the romance between two good looking and stylish characters, but I couldn't really get into that part as much as I should have. Since I also really wanted to be cool and up to date, I was wondering if I should be acting or living like any of these characters, living in a flat with a guy who mooches off me, sleeping around with strangers, dancing at the gas station, etc. The movies have a lot more influence on young people than one thinks.
In my gut, I felt two things: a-My parents would be horrified if I brought friends like that around and more frighteningly, b-I secretly would agree with them.