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For me, Grand Blue is probably the funniest. The timing, facial expressions, and completely unhinged college comedy never get old. Gintama is a close second, especially once you know the characters and all the running jokes.

Great list — I'm especially happy to see Kaze ga Tsuyoku Fuiteiru and Shōwa Genroku Rakugo Shinjū mentioned. Both deserve much more attention. A few underrated anime I'd recommend: ACCA: 13-Territory Inspection Dept. – A slow-burn political mystery with a unique atmosphere and excellent...