 If you liked
Gintama
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 ...then you might like
Samurai Champloo
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Both are set in a historical Japanese setting with modern touches. There is a group of three doing stupid things; there is the bum who drinks and doesn't like to work, but might actually have a dark past (Gintoki from Gintama and Mugen from Samurai Champloo), the glasses (Shinpachi from Gintama and Jin from Samurai Champloo), and the girl who has a very flat chest (Kagura from Gintama and Fuu from Samurai Champloo). Also, the humor style is very similar. . If you have nothing to do after finishing one, you can always try the other! :D