Osomatsu-kun (1988)

The would-be hijinks of the mischievous Matsuno sextuplets are hijacked from episode one by colorful buck-toothed con man Iyami and Chibita, his bald munchkin sidekick. Nearly every episode is a standalone comedy cavalcade with the above cast as well as other quirky locals who show up in a number of different roles as the series shifts effortlessly between time periods and genres, but in most cases, Iyami and Chibita are front and center as partners in crime, a couple of sad sacks scraping by but carrying out scammy schemes in order to get rich quick.

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