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Trivia about Herman's Head includes:

  • Hey, It's That Guy!: Jane Sibbett, who played Heddy, is probably better known these days as Carol Willick, Ross's lesbian ex-wife on Friends; and Jennifer Aniston made a brief appearance.
    • And the boss is played by Jason Bernard, who played Elias' father Caleb in V.
  • Hey, It's That Voice!: Yeardley Smith will always sound like Lisa Simpson.
    • Parodied in one episode, where Louise (Smith's character) tells off an old friend (Maureen McCormick) of the boss without realizing who it is. When the boss confronts the staff about it, not knowing who spoke to Maureen but knowing that she sounded "like a cartoon character", Louise gets an Oh Crap moment—only for the boss to turn and start yelling at another woman, who protests in a Betty Boop voice.
    • Averted by Hank Azaria, who doesn't sound like any of his Simpsons characters.
  • Shout-Out: Many for The Simpsons
    • A Running Gag involved Louise being mistaken for Lisa Simpson every time she talked to someone on the phone.
    • Eventually it got shouted out on The Simpsons, as well, with Lisa covering up a sinister laugh by saying she was "thinking of something funny I saw on Herman's Head."
  • What Could Have Been: According to a writer on the show, had it not been canceled at the end of the third season, a second set of Insiders—for Heddy—would have been introduced in the fourth season.

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