Cromartie High School
Hard not to draw parallels to Azumanga Daioh — a show that I think Cromartie edges out as the funniest anime I've ever seen. Whereas Azumanga feels sweet and dated — not in a bad way, but in that it shows its age and clearly influenced a legion of copycat "cute girls doing cute things" successors — Cromartie, despite coming out a single year later, strikes you as incomprehensibly modern. The closest historical parallel that comes to mind is the Adult Swim extended universe, but whereas those shows lean too far into a kind of nihilistic absurdism that never quite resonated with me, Cromartie has a cleverness with every single throwaway gag or callback that wins you over quickly. I'm shocked there's only a single season of this show; I'm shocked it's not talked about more often.