We all grew up with cartoons, mostly those aimed at kids. With the launch ofThe Simpsons, there was a thirst in that decade for more cartoons aimed at older viewers. Thankfully, more than justSimpsonsclones popped up during this time.

While there were more zany and dry-witted sitcoms, there were also youthful satires, dark comic book adaptations, and slapstick claymation. After having endured the limitations of Saturday morning cartoons, these primetime and late-night shows made me realize how much more potential the medium can have. These are my favorite adult cartoons from the decade when they grew in demand.

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1998-2001

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Based on the Academy Award-winning short film,Bob and Margaretfollowed the dryly comedic lifestyle of the titular British couple. Facing a midlife crisis, the two of them struggle with everything from travel to dinner parties, sometimes exploding on complete strangers with their problems. Their problems mount in the later seasons when they move to Canada, giving the couple more to grapple with in their uncertain relationship.

Although far from the zaniness ofThe Simpsonsand perhaps too dry with its English humor, this series had a certain unexpected crassness. Episodes might start with aSeinfeld-style debate over what to have for dinner, but they can end with Margaret cursing out her friends. The show also had a distinct design with its bulbous-nosed and tubular-shaped characters, adding to the absurdity of the relatable mundanity.

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Tubi

Bob and Margaretis a dry comedy about a British couple struggling to get used to the world as they approach middle age.

1999-2001

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The PJswas a cartoon sitcom set in an apartment complex, developed by Eddie Murphy with claymation by the legendary Will Vinton Studios. Murphy voiced Thurgood Orenthal Stubbs, the building’s crotchety superintendent. While he struggles to keep the building functioning, he’ll also make friends with the quirky community, ranging from the crackhead Smokey to the cantankerous elder Mrs. Avery (Florence Normandie Avery).

The PJswere a real trailblazer for featuring a primarily non-white ensemble cast and claymation that could play and stay in primetime. Eddie Murphy’s stellar voice work lends a lot of credence to the role, and there’s an entire world built from this apartment community with various characters. The scope was grand for the medium, ensuring that claymation could air alongside the traditionally animated marvels like King of the Hill.

The PJsis a clay-animated sitcom starring Eddie Murphy as the superintendent of a struggling apartment complex filled with colorful characters.

1998-2002, 2006-2007

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Before there were Epic Rap Battles of History, absurd mashups could be found onCelebrity Deathmatch. The clay-animated comedy posed as a wrestling event in which various pop culture figures would fight to the death in a ring. The battles came with plenty of topical jokes about the figures, but also an onslaught of brutality with satirical characters being brutalized in the most darkly comedic ways possible.

WatchingCelebrity Deathmatchwas weirdly cathartic. I found the fun in watching celebrities get mocked and mutilated. The claymation made it a little less grotesque, but the wealth of slapstick with the medium is exploited for all its hilarious potential. So if you ever wanted to see Mariah Carey explode Jim Carrey’s head with her singing or the Olsen twins tear each other apart, this cartoon had you covered.

Paramount Plus

Celebrity Deathmatchposes absurd wrestling matches between celebrity figures with clay-animated brutality.

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Cut-out animation made a weird comeback with the odd Comedy Central cartoonSouth Park. Set in a Colorado town, four kids deal with all the strange stuff that happens in their community, starting with the presence of aliens. As the seasons progressed, the stories got weirder and more topical, mocking pop culture, growing up, and small-town quirks.

Although primitive in its simple-shaped animation,South Park’shumor made it the most biting cartoon comedy on cable. The show wasn’t afraid to go to some edgy places, and the eventual quick turnaround time allowed it to be the most topical cartoon on television, animating satire on events from as early as a few days before airing. While the series has gotten long in the tooth in its later seasons, the early 1990s were unique, signaling how crude animation could be so bold and provocative with so little.

South Parkis a satirical cartoon that uses strange and topical humor to follow the exploits of four kids in their little Colorado town.

1994-1995

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At a time when Siskel and Ebert were the most popular movie critics on television,The Criticoffered a silly spoof of their careers. New Yorker Jay Sherman (Jon Lovitz) tries to review movies on his TV show but faces several hurdles with his scrutinizing boss, dry-witted makeup lady, judgy adoptive parents, and underdog son. As he deals with problems of parenting and career, plenty of absurd movies are parodied in the clips on his show.

Developed by the talents who worked onThe Simpsons, this cartoon comedy was made for movie lovers. The various parodies were clever and topical, offering hilarious titles like The Cockroach King and Dennis the Menace II Society. The comedy works so well with the voice talent assembled (Christine Cavanaugh, Maurice LaMarche, Charles Napier), and Jay was iconic enough to garner a crossover withThe Simpsons.

The Criticfollows TV film critic Jay Sherman and his absurd adventures in New York City, laced with movie parodies.

1997-1999

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The Image Comics anti-hero icon graced HBO in animated form without removing a single shade of its dark scenario. The series centers around the tragic Al Simmons, who goes from a black-ops assassin to a casualty via betrayal. He can rise from the depths of hell with a demonic agreement to become a soldier of the underworld, granting him dark powers in the realm of the living.

Spawnwas like a jolt of a cartoon for the high-quality animation in this edgy comic book adaptation. It fit HBO’s standards by boasting plenty of violence, profanity, and nudity, but it also remained faithful to the comics in tone and style. As someone who read the comics then, it was like a dream come true to see that grim world come to life with a richly colored and darkly shaded cartoon adaptation, feeling extra special for one of the few cartoons exclusive to HBO.

HBO Max

Spawnfollows the dark adventures of a wronged man who returns from hell for revenge and becomes a sinister force on the dark city streets.

1997-2001

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Spinning off fromBeavis & Butt-headwas the bolder, dry-witted comedy ofDaria. Having moved to a new suburb, teenager Daria tries to get through high school with her deadpan tone and outsider interests. While she finds kinship with the artistic Jane, Daria’s life is further complicated by her popularity-obsessed sister, Quinn.

With a bolder art style and more nuanced comedy,Dariawas a cartoon relatable enough for teenagers and well-written for adults to find funny. There was a charm to how Daria navigated through her life problems with wit, but the show also grounded her enough to deal with crushes, piercings, and trauma in a surprisingly mature manner. She was a fully realized character, making it no surprise that her show lasted for five seasons and two TV specials.

Pluto TV

Dariafollows the day-to-day problems of a dry-witted teenage girl navigating her suburban world with deadpan punchlines.

1991-1995

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Peter Chung delivered one of the most intoxicating cartoons of the 1990s withÆon Flux. Set in a dystopian future, the vigilante Æon strikes back against the oppressive Breen, led by her on/off lover Trevor Goodchild. Her adventures find her dealing with strange sci-fi discoveries of mind-wiping drugs to body-altering alien visitors.

WhileÆon Fluxmatched the rough nature of cartoons on MTV, it was weirdly sexual and provocative in its surreal sci-fi staging. Each episode felt strangely dense with its setting and themes while embracing a weirdness in its style of revealing clothing and rail-thin characters. For daring to be more erotic and esoteric, this was one of the more challenging cartoons on 1990s TV, and was such a treat to return to years later.

Æon Fluxdepicts the surreal and sexy adventures of a vigilante in a dystopian future, dealing with all manner of oppression and strangeness.

1994-2008

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Cartoon Network found something fun for Space Ghost to do with his talk show,Coast to Coast. The cartoon superhero interviewed celebrities and asked increasingly absurd questions as the show went on. In addition to his struggles as a talk show host, Space Ghost must also deal with his villains, Zorak and Moltar, who constantly sabotage the show.

As a foundation forCartoon Network’s Adult Swim block,Space Ghostwas a highly subversive show beyond the gimmick of cartoons interviewing live-action celebrities. It took some time to find its voice and humor, but once it became more gonzo, it was the most hilarious show ever. Nothing is funnier than watching Space Ghost ask his guests the stupidest questions and how they react, especially with George Lowe’s flawless performance as the superhero.

Sling TV

Space Ghost Coast to Coastfeatures the classic cartoon superhero interviewing celebrities in a talk show format.

1993-1997, 2011, 2022-2023

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It was the infectious laugh you couldn’t help but replicate.Beavis & Butt-Headwas MTV’s satire king for posing the titular teens as the dumbest examples of the MTV generation. When they weren’t making absurd commentary on music videos, the duo was causing trouble in school, at their fast-food job, and being a general nuisance to their middle-aged neighbor, Mr. Anderson.

Although crudely drawn by Mike Judge, there was a genius to the simple-minded satire ofBeavis & Butt-Head. The characters were dumb, but were presented in a way that the world misread their mindless meandering. There was an enduring charm to the dim-witted youth that they continued their antics in the form of movies and sequel series.

Beavis and Butt-headis a satirical take on dumb teenagers who stumble into trouble and constantly laugh.

Adult cartoons of the 1990s were refreshingly diverse, with various genres and mediums. The realms of traditional 2D and claymation were expanding to more than family-friendly entertainment on both network and cable TV. This primordial ooze enabledadult animation to thrive, and it’s important to learn the history and appreciate the freedom of these shows.