(I think the OP should be titled "Most Ridiculous Anime You've Seen"... it'd probably make more sense because I thought this was going to be a thread for an anime I had never heard of.)
Chu-Bra!! is one of those extremely rare series where you go into for lewdness but it instead turns out to be frightening informative and has good characters and story
Like Futari Ecchi
True that. Now you got me curious about
Chu-Bra!!.
Pupa was ridiculous in just about everything, from its poorly-executed premise due to the four-minute run time per episode, to the awful censoring, and to the awful incest. I seriously don't know what I was expecting from it the first time around, but I guess I didn't do research well enough or else I would've caught the incest before it aired, it almost felt forced even though it had been part of the plot from the start. Apparently.
For a more serious, positive answer of what ridiculous shows I've seen, I've seen quite a bit, but
Gonna be the Twin-Tails!! and
Samurai Flamenco best come to mind of fairly recent anime. I think both of them were affectionate parodies to begin with (though
Flamenco was more of a reconstruction of the superhero genre, and the ride was fun), and yet it was clear the shows were just having so much fun that I couldn't help falling in love with everything no matter how ridiculous it seemed. It's probably also a reason why I like
Binan Koukou Chikyuu Bouei-bu LOVE! even though it's a magical boy anime, it's stupid, and yet it's enjoyable.