 If you liked
Sakigake!! Cromartie Koukou
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 ...then you might like
Sakamoto desu ga?
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Both are surreal and over-the-top high school comedies with very similar tone and comedic timing. Sakamoto would have fit right in if he transferred to Cromartie High.
These shows feel so close that I'm sure the author of Sakamoto was a fan of Cromartie High School. They both feature school delinquents and over the top humour.
Cromartie high school is a delinquent school, it's a lot weirder than Sakamoto but it gives you the same feeling of randomness. Well, you'll just have to try it for yourself. This is just how I feel.
These series revolve around over-the-top situational "gag" comedy expressed in a deadpan manner from the main characters involved. Sakamoto's actions mirror that of the everyday lives of the Cromartie Highschool attendees. They rely on slapstick humor to add a bigger punch to their comedic gags. They're also both set in a high school full of delinquents and are carried out in a similar SOL fashion. If your sense of humor gravitates towards this "deadpan meet absurdist" style of comedy, then what Sakamoto and Cromartie play around with would feel right at home with you.
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Recommended by ZephSilver
Both series are very off the walls in their comedic style and leave you in stitches due to how stupid some of the humour is such as Sakomoto being able to run on walls whilst Cromartie has a gorilla and a robot as classmates. Both focus heavily on the lives of delinquents and involve lots of hilarious adventures with them in various comedic skits
ITS THE MCS, THEIR COMMENTARY IS THE FUNNIEST, THE SIDE CHARACTERS ARE HILARIOUS
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Recommended by yoshida_hirofumi