Alternative Character Interpretation: Miss Shaw. An idealistic teacher with bold new ideas that was unfairly driven away by a conservative school board that never gave her ideas a chance? Or an irresponsible teacher with terrible ideas that walked out on the students that needed her when she was forced to compromise with the school board? Lampshaded at the end when Adult Kevin notes that he didn't know if he should be angry at her or the school board.
Confirmation Bias: A rather nasty case with Kevin's civics teacher. He does a number of prickish things, but Kevin only decides that he's irredeemably evil when it becomes apparent that he's a Republican.
"Funny Aneurysm" Moment: In "Steady as She Goes", narrator Kevin says that Carla Healy was the only woman in Paul's life who wasn't a blood relative. In later seasons, she is no longer seen or mentioned, and Paul is rarely shown to be involved with other women (though he did lose his virginity in one episode).
Harsher in Hindsight: The first clip show ends with a montage playing over a recording of the song "In My Life". One of the lyrics is "some are gone and some remain", with the "some remain" line playing over a clip of Jack Arnold, implying he's still alive. However, in the last episode it's revealed that he died two years after the events of the last episode. On the other hand, the "some are gone..." part plays over a clip of Grandpa Arnold, whose death was never confimed on the show.
In the episode "Heart of Darkness", Paul says that he's allergic to contact lenses, but in the last two seasons he switches to contacts. In the episode before he starts wearing contacts, when Winnie informs Kevin that there's something he doesn't yet know about Paul, one of Kevin's guesses is that he's wearing contacts.
Jerkass Woobie: Becky Slater. Disproportionate Retribution aside, Kevin was the one that hurt her first. He's the one that asked her to go steady when he really still liked Winnie, stringing her along and using her to make Winnie jealous until she got wise to it and broke up with him. Then he got her to take him back by lying to her about not liking Winnie anymore and only finally came clean with her and ended it when it became clear that Winnie's current relationship was over and that Winnie might still like him. It's understandable that she would hold a grudge against him after all that; even if she did go too far with it at times.
They Wasted a Perfectly Good Plot: While it would have been hard to really focus on it since the shows entire focus was on Kevin and the last episode ended during the summer, it's a shame that they couldn't have shown Chuck and Jeff's summer road trip in the last episode, or even have the narrator reveal anything that happened to them on that trip.
The Woobie: Winnie, to a degree. In the first episode she loses her big brother, and her family never really recovers. She leaves her childhood home and goes through a rough period in the 3rd season, and it's implied she has some insecurity issues in a few episodes, particularly the ones where she hangs with the "cool kids" and tries to change who she is.
Growing the Beard: They've impressively managed to continuously do this album after album since "The Upsides."
Old Shame: Soupy really doesn't like "Get Stoked On It" and feels that it created a very bad first impression of the band to many. No one else in the band really likes it either but they don't quite share the same level of disdain Soupy has for it.
Face of the Band: Dan "Soupy" Campbell to some. Most of the songs are about his experiences (combined with some of the other band members' in a couple songs).