Looks like I got ninja'd on most of the big dogs, I'll have to come up with some more creative choices...
Michiko and Hatchin
Fantastic series, even though it's very very western-centric in terms of writing and presentation (I'd go as far as to call it Taranteno-esque). It's got a really cool visual style it's dark as hell but has plenty of genuinely funny moments, and it's by most of the same people who made Cowboy muthahfuckin Bebop so that's gotta count for something.
Jojo's Bizarre Adventure
I'm specifically referring to the newest ongoing adaptation of Jojo's which started in 2012, but I also like the OVA from '98, it's pretty good too in it's own right. But Jojo's 2012 is pretty much the closest thing to a perfect adaptation of the manga you could ask for, it retains all the delightfully over the top characters, stories, and dialog that characterize Jojo's, and make for a very addicting and entertaining series. It's never been a better time to start either because the new season (titles "Stardust Crusaders" after the title of the manga arc it's an adaptation of) is still only about halfway through, and it's often considered the high point of the entire series!
Princess Jellyfish
This one struck a more... personal chord with me, it's a more acquired taste then the others I've mentioned and it's not for everyone, but if you're in the right state of mind this show has the perfect mix of clever writing that manages to be both very funny and very serious (sometimes at the same time), ingenious art direction and character design, and it all just amounts to a very enjoyable show overall.
Also, Kuranosuke is the model of who I aspire to be as a person, just sayin'.
Watamote
Again, kind of an aquired taste, but if you had a highschool experience that was anything like Tomoko's (EG: being the introverted, socially incapable, recluse who'd rather being gaming or watching anime then doing... anything else; Read: Me) then you are going to LOVE this show. If you didn't... then this might come off as the single most mean spirited thing you've ever watched, it's that subjective. I've known people who consider this the best anime ever made, and I've known people who were terrified and disturbed deeply by it.
All I can say is give it a watch, you'll just have to see what you think.
Oh and it's been said but...
Panty and Stocking, Panty and Stocking, Panty and Stocking, PANTY AND STOCKING!!!
It's my favorite anime and I hope it becomes one of yours too!