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  • And You Thought It Would Fail: A number of critics predicted the series would be the first of the Fall 2000 batch to be cancelled. Oh, it did end — after six seasonsnote .
  • Fan-Preferred Couple: Quite a few fans ship Greg and Christine, mostly due to Kim's Scrappy status, despite the canonical marriages of Greg to Kim and Christine to Jimmy.
  • Hilarious in Hindsight:
    • Greg tells Jimmy to stop thinking about sex, to which Jimmy says "That's like Tiger Woods not thinking about sex" due to Woods having a reputation for monk-like dedication to golf at the time. Fast forward to 2010 and Woods became embroiled in scandal after scandalous details about his personal life were revealed to the public.
    • In one episode, Jimmy unintentionally tells Kevin Smith that his latest film (a WW2 comedy) sucks, at first Smith gets offended and demands an apology, but then he later admits to Jimmy that his film really does suck and he ends getting more funding to do a different film. A very similar scenario ended up happening with Smith in real life, after Smith directed Cop Out, Smith was pissed at critics for the negative reviews, then he later admitted the film really wasn't very good, and that was a big part of his decision to make Red State.
  • Informed Wrongness: Explored in "March Madness."
    • Played straight at first, when Greg gets tickets for the NCAA Championship game but Kim guilt-trips him into attending her grandmother's birthday party instead.
    • Next, it was deconstructed by Christine when Greg gave Jimmy the tickets. She got mad at Jimmy for trying to get out of the party, but she then explained that she really didn't care what he did...she just planned to hold it over his head.
    • Then, it was initially subverted when Greg missed an important photo...the entire reason he couldn't go to the game...because Kim made him go buy ice. Although initially furious, Greg starts to enjoy the guilt being on the other foot.
    • Finally, Jimmy and Billy come back from the game and told him how miserable it was and what a terrible time he would have had (which was a boldfaced lie intended to lessen Jimmy's punishment from Christine). This double-subverted it, with Kim once again assuming the right.
  • Quirky Work: For a generic show, the series had its share of weird episodes. Taking the cake would probably be "Halloween," which starts out as a pretty standard episode but ends in a huge Mind Screw involving Greg and Jimmy in bed with an elderly woman.
  • Retroactive Recognition:
  • The Scrappy: Kim. She basically treated Greg's secretaries as slaves to do her bidding (and gave Greg an undeserved Bad Boss reputation) and was repeatedly obnoxious and prudish about everything from raising her children to how she wanted Greg to do things...yet she was often seen as being in the right more often than not.
  • Seasonal Rot: Began to hit in Season 5, and was in full-stop mode in Season 6. The story arc where Greg is unemployed is difficult to watch, and short-haired Kim falling to Christine's level of apathy about her marriage and children stood in pretty jarring contrast to her bubbly, neurotic character in Season 1.
  • Unintentional Period Piece: Occasionally, this show is a time capsule of late 90's and early 2000's child culture, featuring references to such shows as The Wiggles and Blue's Clues, with the latter episode even having Sammy watching said show using a VHS tape. In addition, one episode's plot was centered around Emily Warner's birth being covered by A Baby Story, a popular reality show during that era.
  • The Woobie: Greg. His wife ignores and walks all over him; his in-laws mooch off of his generosity; his boss takes him for granted and is prone to bizarre, off-the-cuff decisions that he has to try and implement; his new friendships, few of the good things that happen to him, all end quickly because his family gets jealous. Nevertheless, he continues plugging along.

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