What's really wrong with Troy.
Winona Ryder's character really nailed it when she told him that if he really wanted to make it as a singer he needed to practice at least 3 times a day and play somewhere other than the coffee house.
She also nailed him when she said that life doesn't owe you anything.
Troy wants the reward without doing the work. He's smug and overly impressed with himself. His comment about an IQ requirement clearly demonstrates his arrogance. He is a poser.
I saw the ending as tragic. Troy is going to screw the relationship up because he's emotionally immature. When he tells Michael we all die alone and Michael asks him what he's looking for outside on the street that demonstrates that Michael has a far greater understanding of what relationships are about. The irony is that Troy's father doesn't die alone. Troy is at his side.
Did Troy have an epiphany when he saw his father die? He probably did but it will be short-lived.
Michael is not the right guy for Winona either. He might be in another 5 to 10 years but not at that moment. She's still naive and idealistic and hasn't learned what reality is yet. It's extremely unrealistic to expect that a TV network is going to give carte-blanche to a first time filmmaker and buy a show that will tank in the ratings. Her documentary would've been right for the Sundance Film Festival but airing it on "MTV" would have teenagers clicking the remote faster than you can say Reality Bites.
Seeing this movie 16 years after it was originally released gives clarity to what the filmmakers thought of the time they came of age was all about. It oozes with self-importance, judgmentalism and naivete. In other words it was a perfect reflection of the time.