YMMV / Skippy Dies

• Esoteric Happy Ending: Lets see here. Two pedophiles, an adulteress, a grossly negligent friend of Skippy’s who let one of the other friends take the blame for Tom’s death and Carl get away with their various crimes not only scot-free, but even get the lives of their dreams in the process, with only the latter wallowing in self pity. And the silver lining is... two people don’t kill themselves. Yeah, real happy ending there.
• Jerkass Woobie: Lori. Early scenes show her engaging in a mean, racist prank, and she cheats on Skippy, breaking his heart. But she's also engaged in a somewhat abusive "relationship" with Carl that mostly involves exchanging sex for drugs (which she wants because of her insecurity about her body), and you can't help but feel for her when he films her questionable-consenting blowjob and sends it out to the whole school, and she panics, thinking she's pregnant. The last section of the book reveals her to be desperate for love and with few real friends, which drives her to suicide.
• Rewatch Bonus: The more you reread the book, the better you understand what's going on. For example, you start to recognize the ton of Foreshadowing that Skippy was molested by his swimming coach. And you start picking up on all the Harsher in Hindsight moments.
• Too Bleak, Stopped Caring: This whole series chronicles the slow descent of Skippy and his friends into tragedy , from adultery and constant harassment to pedophilia and gross negligence. And as noted in Esoteric Happy Ending, every perpetrator involved either faces no comeuppance or positive consequences for their actions.
• The Woobie: Skippy. He's a sweet, innocent, Adorkable kid who is the center of his friend group. The first two thirds of the book detail his life getting destroyed under a gauntlet of assaults: getting bullied at school, dealing with his mom's slow death, having his heart broken in a shocking way, being raped by his swim coach, and becoming addicted to drugs to cope with it all... And then he dies at the age of 14. Heartbreaking.