I'm glad you guys got me to watch Cowboy Bebop, even though I was kinda the only one. I'm gonna make a couple recommendations, even though nobody seems to have time to do these rewatches consistently. I think after a heavy drama anime like Bebob, we should watch a more laid back comedy type of show.
Lucky Star - Basically anime Family Guy.
Haiyore! Nyaruko-san - A romcom set in the Cthulhu Mythos. Probably my all time favorite. I still haven't watched the third season.
Watamote - The misadventures of a girl with crippling social anxiety. I should warn you, this one can be extremely cringe-inducing, especially if you've dealt with something similar.
Nichijou - Never actually watched myself, but I've heard good things about it.