This is an unconventional one, but clearly fits

Sayonara, Zetsubou-sensei (SZS).

I just love the cast. The wordplay is amazing and the fan translations that I read from years ago have so much passion explaining complex Japanese word play and cultural references and SHAFT managed to adapt 3 seasons and 3 OVAs for it before they exploded with Monogatari series and PMMM to the point that I resent them for not doing anymore SZS lol