Nobody talks about this one. A rich kid and his servant living in absurd poverty, the premise alone is the joke, and the show milks it for 164 episodes without ever running dry. Every episode is a self-contained gag machine built on character chemistry so natural you forget you're watching a 1989 kids' show that somehow never got tired of itself.
Obocchama-kun is a comedy TV anime from 1989 that ran for 164 episodes. Its source is a children's manga by Kobayashi Yoshinori that received an award and originally appeared in CoroCoro Comic, the Shogakukan magazine. The long-running series brings that comedic manga to television for a young audience.