 If you liked
Sakigake!! Cromartie Koukou
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 ...then you might like
Gintama
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Their sense of humor is pretty similar. If you enjoyed either of them, you will definitely like the other one as well.
I think creator of Gintama inspired a lot from Cromartie High School; both anime have somewhat similar sense of humour; both are comedies that float on the edge of absurdity. Yet only their comedy features are similar. Unlike Gintama Cromartie lacks a solid plotline and strong characters; in other words, cromatie is pure comedy.
Gintama is a mix of the past and future, while Cromartie High deals with present day life. However, both animes are hilariously exotic and whacky, pushing the limit of random episode plots. Both animes also show off a bigger cast of main and sub characters. If you're looking for comedy, look no further.
Cromartie's "talking" segments remind me quite a bit of those in Gintama. However, I think Gintama does it better, somehow. I prefer the Cromartie manga over the anime, perhaps because I can "time" the gags better in the manga than the anime does.
Similar style of comedy with the viewer expecting something crazy, yet still being surprised enough to make it funny. Often parodies many genres of anime.
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Recommended by wolffanghameha
They have the same type of random and hilarious humor, you'll have to laugh a lot watching both shows.
The real-world celebrities that are parodied in the shows are also extremely funny and on point.
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Recommended by Illuminatli
Very similar type of jokes that often go overboard and transcend any common sense. Also gorilla characters and charismatic robots in both. In a sense Cromartie Kokou is a direct predecessor of Gintama and therefore a definite must-watch for all Gintama fans.
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Recommended by StudentMAGe
a similar sense of humor
both are hilarious & GOLDEN! and have a different style of "Humor" and most people can't understand why it's funny lol.
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Recommended by BrawlerJoe
I heard you like comedy. Have no fear, Cromartie High School is everything that Gintama's not - and that's funny. That's right, Cromartie High School is an actual comedy with actual jokes, subtlety, timing, and payoff. It's a comedy that doesn't rely solely on the repetition of the same dozen or so gags every single episode and ham-fisted references where the punchline is the fact that it's a reference. Enjoy.