When The Simpsons premiered on the Fox network in 1989, the show that everyone compared it to was The Flinstones, it was the only other animated sitcom of its kind. It seems silly today, but before The Simpsons, animation on television was almost exclusively targeted for children, and prime time animation was practically unheard of. Even The Flinstones, which premiered in a prime time slot, was eventually bumped to Saturday morning. But The Simpsons, with its tremendous success, proved that animation could not only survive in prime time, but that it could also be made for older audiences. As a result, the 90's saw a boom of animated prime time shows aimed at adults, many of which were, well, frankly, terrible. Adult animation was a new concept on television, and it took a lot of trial and error before television creators could figure out what worked and what didn't. Never the less, while there were a lot of duds, there were also lots of gems that came to be during this time of experimentation. Sadly, many of them were never given much of a chance to succeed due to those before mentioned problems, but thanks to syndication, and networks like Adult Swim and Comedy Central, these shows would eventually find a small audience. This is part one of a two part (maybe even three?) article composed of what I think are some of the best underrated 90's adult animated shows, in no particular order.

1. Clerks: The Animated Series

Based on the movie of the same name, Clerks: The Animated Series was picked up for six episodes, of which only two were aired, and the world is a poorer place for it. Clerks was so much better than an animated show based on a years old independent film had any right to be. Like the movie, it's centered around the misadventures of Dante and Randal who try to stave off boredom at their jobs through hair brain schemes and nerdy debates, occasionally joined by dealers Jay and Silent Bob. Unlike the movie, however, the animated format allows Clerks to leave behind the restrictions of reality and embrace animated anarchy to its fullest. This was a show way ahead of its time in the way it play on the conventions of TV sitcoms. Take, for example, the second episode of the series entitled "The Clip show Wherein Dante and Randal are Locked in the Freezer and Remember Some of the Great Moments in Their Lives." As you can probably guess, it's a clip show, but with only one episode to flashback to, it's one of the best clips how parodies ever. Sadly, the joke was completely lost upon first airing, since ABC chose to air the fourth episode first, followed by the second episode, thus completely gutting the joke. The show was then cancelled after that, and the remaining four episodes ended up being run in syndication on Comedy Central, where it developed a dedicated cult following. Kevin Smith has threatened to bring it back, but until that happens -- if it happens -- at least we still have these six episodes which are definitely worth tracking down on DVD, which has some of the best extras and commentaries ever.

2. Capital Critters

There were a lot of terrible shows to come out of the 90's animation boom, but while I wouldn't say Capital Critters is a good show by any stretch, it is a fascinating one. Created by Hanna-Barbera (there's your first red flag) the show is centered around a group of mice living in the White House basement, oppressed by the villainous fat cats, sort of like a really obvious political cartoon, and much like a political cartoon, it is painfully obvious on almost every level. The animation is dated, the voice acting sounds like it's out of Scooby-Doo or the Flintstones, except now they're tackling subjects like gun control, race relations, sexism, environmentalism, and even nuclear arms race; all of which are handled with the subtlety you would expect from a cartoon from the people that brought you Wacky Racers. Oh, and did I mention there are other animals living down there and they each represent a different ethnicity. You know all those old cartoons from the 1930's that Disney and Warner Bros don't want you to see? Capital Critters should probably be buried in the same vault. Capital Critters is a show that has been burned into many people's memories from being constantly rerun in syndication during the early years of Cartoon Network. If you're curious, you can find the entire series run on YouTube. Not good, but definitely worth checking out for just how odd it is.

3. Duckman

Speaking of odd, Duckman is probably one of the more successful shows on this list, having lasted a total of four seasons. Based on the indie comic by Everett Peck (you youngsters might recognize his as the creator of the equally strange Boy and Squirrel.) The show is about a widowed and angry anthropomorphic duck named, you guessed it, Duckman --voiced to perfection by Jason Alexander -- who works as a detective in LA, living with his dysfunctional family, including his sister-in-law who looks exactly like his deceased wife, Beatrice, except she hates his guts, only further adding to his misery. Some of the best moments in Seinfeld were when George Catania goes on a rant, Duckman had about one per episode. Duckman's constant anger and frustration with modern life where most of the show's humor stems from, and what I admire about the show is that while most of them are ignorant and stupid, Duckman occasionally makes some good points. My personal favorite Duckman rant is when he critics a comedian whose humor lacks any bite, and how people are manipulated into liking comedy that's clean and thoughtless by comedians, here represented by King chicken. In addition to its off the wall dark humor, it has an equally off the wall animation style by Klasky Csupo, which you may recognize from Rugrats and early Simpsons. I highly recommend checking this out. Plenty of the episodes are available on YouTube, but here's a sample that does a pretty good job of summing up Duckman and why it works so well. Most frustrating is that the series ended on a major cliffhanger that has never been addressed. Although Everett claims that he knows how the series will truly end and is still planning on continuing it someday, it seems doubtful that will ever happen. Too bad, because I think Duckman could really work in the modern day very well.

4. Dr. Katz Profession Therapist

This is barely and animated show. More of a way for Comedy Central to package and resell stand up routines, Dr. Katz features the titular doctor as he deals with his strange clientele, while trying to get his twenty-something son out of his house. The show is most notable for squigglevision, one of the worst, yet oddly charming animation gimmicks ever conceived and featuring a smorgasbords worth of comedians like Ray Romano, Louis C.K., Conan O'Brien, Kristen Schall, and more. It was also one of the first notable appearance of John Benjamin, who voices Dr. Katz's lethargic son, and would go on to voice some of the funniest animated characters in shows like Bob's Burgers and Archer. The show also featured something rare in animation, voice actors would actually record lines at the same time, giving the dialogue and more natural and improvisational feel, it truly was unlike anything that came before. Although to call it "animated" may have been a bit of a stretch. The show had very limited animation, and honestly, it kind of hurts the eyes to look at it for too long. But the voice acting and writing were so sharp, it practically didn't matter. If you can get past the squigglevision, Dr. Katz is one of the most hilarious animated shows, almost like a sampler of different comedians. The improvisational nature leads to a lot of great moments and lines which I still quote regularly today.

5. Mission Hill

Created by Simpsons alumni Josh Weinstein and Bill Oakley, Mission Hill told the story of a group of twenty-somethings living in a San Fransisco/New York-like metropolis, primarily centered around brothers Andy (a struggling cartoonist) and Kevin French (his nerdy seventeen year old brother), dealing with the difficulties of the realities of growing up, while also trying to remain cool and hip. It was an urban hipster fantasy that was both loving as well as mocking of its subject matter. Featuring a cool indie comic book art style reminiscent of David Clowes, as well as one of the first gay couples in a prime time show, Mission Hill was cool, hip, and not long for this world. Weinstein and Oakley have stated that it might have been due to the lack of a family, pointing out that the most successful adult animated shows up to that point had all revolved around ten family dynamic. They may be right, but it's a shame, since Mission Hill was clever, funny, and surprisingly daring. It featured one of the first openly homosexual couples on television, not just as caricatured punchlines, but as real characters. Its unique settings allowed it to tell stories outside of the usual sitcom stories. It talked about what it was like to be an aimless young adult and dealt with the problems of modern life with a unique satirical edge and apathetic youthful eyes. In its short run, the show resemble managed to tell hilarious and thoughtful stories in the same way many of Oakley and Weinstein's best episodes of The Simpsons had been. Like many of the shows on this list, it got a cult following via reruns in syndication, especially in the early days of Adult Swim, where it developed a cult following. A show too far ahead of its time, perhaps. I highly recommend it, especially if you're a twenty-something yourself.