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  • Base Breaker: Winnie. Some people love her and see her as the quintessential Girl Next Door, while others take offense to the way she treated Kevin at times, especially when their relationship was up in the air.
  • Crowning Moment of Funny: The Gym teacher's utter failure at drawing the female reproductive system ("It looks like a COW").
  • Retroactive Recognition: "Hey, it's The Doctor from Star Trek: Voyager as the asshole Gym teacher!"
    • And Karen is married to Ross from Friends, you do remember Karen don't you?
  • Tear Jerker: Built on a metric ton of these. Special stand-outs include the first episode's final revelation, Kevin's "I love you" to Winnie while she's sick at home, Kevin failing his piano recital utterly and admitting (in narration) that he doesn't even remember how to play anymore, and the Series Finale's ending commentary.
    • The entire Series Finale has to be one of the saddest, yet most enlightening in TV history.
    • Wayne breaking down and crying on his father's shoulder at the end of "Private Butthead." He'd been struggling with SAT prep to the point where he decided he was better off skipping college and joining the army with his friend Wart, but he fails the physical due to psoriasis. Thinking he really has no future now, Wayne breaks down crying on his father's shoulder.
      • The sixth-season opener is a follow-up to the army test. Wart comes home from Vietnam a changed man, hated by everyone for taking part in the war at all. Wayne finds him crying in the parking lot in his underwear after a football game, whereupon Wart says "nothing seems to fit anymore". Wayne gives Wart his shirt, then a warm hug as he reassures him he's still his friend.
    • Mr. Collins's death, but also the lead-up to it. Kevin feels like he's been bonding with Collins as he helps him study for a midterm, but one day he can't make it and Kevin feels hurt and betrayed. He flubs his midterm on purpose, only to come to school after the weekend and learn Collins passed away. Kevin takes the loss hard due to his guilt over being so childish, ends up retaking the test, and sees the spirit of his teacher as he leaves the classroom. Linda Ronstadt's "Goodbye, My Friend" playing over the last few minutes and the "in memoriam" yearbook page really bring home the feelings.
  • Values Dissonance: When Grandpa Arnold brings Kevin a puppy as a surprise present. These days, it's heavily advised not to give animals as gifts without checking with the recipient first, as many of these pets end up in shelters due to the recipient's inability to properly care for them.
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