I caught an episode of 1999's animated series Mission Hill years ago, and remembered nothing from it except that it seemed amusing but surprisingly mature and sweet for an Adult Swim show. Mom chose it off my Amazon Wish List (probably do to the lack of cleavage, weapons, and blood on the cover) and gave it to me Christmas Eve. By the time I went to bed late Christmas Night I had watched all 13 episodes.
It's the story of three roommates living in an apartment in the trashy-but-trendy fictional Mission Hill neighborhood. I'd assumed based on the name that it was supposed to be in San Francisco, but the commentary says it's largely based on Chicago's Wicker Park. One of the roommates, a cartoonist, grew up the in the surrounding suburbs, and when his parents leave for Wyoming they leave his nerdy 17 year-old brother behind to live with them while he finishes high school. They have antics.
The first few episodes were a little clumsy, but the same sweetness and maturity that I'd noticed the first time got me to keep watching. And I'm glad I did, because they get much funnier and more elegant as time goes on, culminating in a few brilliant ideas that will keep me re-watching.
Apparently the show was made for the WB by some ex-Simpsons folk who "were tired of having almost no characters between 12 and 30". WB cancelled them after episode 2, Adult Swim picked them up, and the rest is I imagine a whole lot of repeat broadcasts. This explains the un-Cartoon Network-y tone and episode length (half-hour), as well as the Simpsons-esque crowded backgrounds and joke signs you almost can't catch without repeat viewing.
If you choose to give it a try (it's on DVD in 2 disks) and don't want to unshakably commit to watching the whole thing, the best to start with may be Episode 4: "Andy Vs. The Real World", in which the entire neighborhood flashes back to what it was like when MTV came to town. It doesn't require knowing a lot of backstory and the comedy is more refined than in the premiere.
But the best episode by far is 10 ("Kevin Finds Love"), in which the younger brother for unworthy reasons starts dating the most unpopular girl in school, Eunice Eulmeyer (voiced by Jennifer Jason Leigh). She's fantastic, kind of what Luna Lovegood might be if she faced the world with bitterness rather than whimsical resignation. Plus, Water Balloon, she has a uniquely scientific way of expressing herself. Got that, Chimpy?
There are also 5 unshot episodes, with unfinished scripts available online. Finishing these is another thing to add to my list of "things to do when I become a millionaire".
The other funny thing, discovered much more recently, is 11 Central Ave, the "radio comic strip". A weekly 4-minute podcast (free at iTunes store) about the realtime goings-on of a family and their friends around the breakfast table. Thus far there've been more misses than hits, but their ratio has been getting slowly better and there's very little commitment required.
The best episode, BY FAR, has been #64, "A Stranger At The Door". Most of them are just kind of topical and sarcastic, but this one transcends that into the realm of existential/absurd-ist theater. "Full of TASTES!" Definitely listen to this and the following episode (#65) first.
Earlier episodes that particularly amused me, in a lower-key way: #26 (Clocky), 49 (Senior Charades), 30-34 (Bollywood, Crowdsourcing, Drinking & Cheney, Annelise is Grounded, Virtual Reality), 48 (Limerence).