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  • Crosses the Line Twice:
    • The WW Lazers restaurant's doo-wop singers, with Franklin Roosevelt on the keyboard, Tojo on the electric guitar, and Hitler on vocals.
    • Stealing money from a fountain at a mall? Horrible. Stealing money from a fountain that was supposed to grant sick children their wishes as they stare at him stealing from them? Hilarious.
    • The Mayor calling Gibbons "it" during "Surprise Party".
  • Ho Yay:
    • It's all but outright stated between The Mayor and Dr. Ian Black.
    • The Mayor and Saul as well.
  • Referenced by... Satan can be seen watching the intro during the first episode of Lucy, the Daughter of the Devil.
  • Retroactive Recognition:
    • In what has to be the most bizarre example of this possibly ever, the voice of Joy Peters is Stephanie Courtney, who two years after the show ended would become world-famous as Flo, the Progressive Girl.
    • Zach Galifianakis as Dr. Vickerson, a few years before he hit it big with The Hangover.
  • Squick:
    • The Mayor feeding an unconscious Tom wet cat food for several weeks in "WW Lazers"
    • The guests at Brindon’s memorial were served a gelatinous “meat cobbler” in “Puddins”.
  • Too Bleak, Stopped Caring: Part of the reason Tim and Eric moved onto other projects is that the show's ratings were miserable thanks to this trope. After a while, once it's clear Tom will be screwed over every chance the show gets, you stop caring enough to watch, especially considering this was the only recurring joke the show really had. The show's mean-spirited cast and overall cynical atmosphere don't help matters either.
  • Unintentional Period Piece:
    • The constant mention of CD-Rs, the employment of hipstery, cheerful muted horns with big, blocky, colorful text in the end credits, and Tom's use of both a BlackBerry-esque device and MySpace-like social network all point to this show taking place in a very specific timeframe, around 2004 to 2006.
    • “Gibbons” has a scene that claims Prince Charles is coming to the friendship convention that episode (he never showed up for unknown reasons). As of May 2023, Prince Charles is now King Charles, making the episode outdated.
  • The Woobie: One can't help but feel bad for Tom, whether it be due to Executive Meddling ruining his ideas or his Awful Wedded Life to Joy. Special mention goes to the episode where his stepson explodes after overeating at a buffet. Tom is basically a crying, depressed wreck by the end of the episode.

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