Adult animated comedies have many more misses than hits. For every South Park or Seasons 2-5 of Family Guy, there is Brickleberry, Allen Gregory, Ren and Stimpy: Adult Party Cartoon, The Cleveland Show, Bordertown, Glenn Martin DDS, or Seasons 10-13 of Family Guy waiting to ruin your evening. Even the adult comedies that manage to be decent do so only through their ham-handed attempts to mimic The Simpsons or South Park, rarely providing any genuinely fulfilling entertainment.

If primetime adult animation does not satisfy, the ambitious viewer can try their luck with Adult Swim’s “alternative comedy.” More often than not, however, Robot Chicken and Metalocalypse get drowned out by Mr. Pickles, King Star King, 12 oz. Mouse, or Brad Neely’s Harg Nallin’ Sclopio Peepio. Even among Adult Swim cartoons ostensibly considered good like Aqua Teen Hunger Force, Squidbillies, or Superjail!, the style is often so niche that it can isolate many potential viewers (whether that is fair or not).

Adult cartoons, in my opinion, tend to fail because they try to shock and satirize without having the talent to do so. They see the success South Park or The Simpsons has had moralizing and pushing the envelope with their adult audience and think that they can do it too, yet their teams rarely have the comedic chops or story-telling skill to shock in a way that adds anything to the production. What they end up with is something that can only inspire morbid fascination as the show frantically rebels against self-imagined external tyrants.

The shows on this list, however, exemplify the full potential of the TV-14 and TV-MA ratings. They use the mature subject material to say unique and sometimes contentious things. Either they explore concepts that rarely feature in media, or they explore familiar concepts in a refreshing way. They also refuse to let their messages get in the way of creativity. Each of the shows featured on this list avoided the trap that many adult cartoons fall into, sacrificing entertainment and humor on the altar of a message. They perfectly balance the fun with the thought. Simply put, they treat their audience like adults: sometimes they need bacchanalian entertainment, sometimes they need to question their world, and sometimes they need to bite the bullet and admit that they suck.

#5 — American Dad/Futurama

The secondary projects of Matt Groening and Seth MacFarlane are, in my opinion, superior to the works audiences know them for. The Simpsons is a good show. Even at its worst, The Simpsons still manages to be decent, but catching up on all 600+ episodes of this animation behemoth drives home how disconnected I am from its origin. Deconstructing family sitcoms polluting broadcast television at the time also drove a wedge between the show and me. I only ever grew up with the occasional episode of Full House, so I am removed from what gave The Simpsons its edge.

I had no such problem with Futurama. Setting the show one thousand years in the future meant that the comedy could utilize the same conventions that have kept science fiction relevant. This show juxtaposes the technology of a purportedly advanced era with the universal problems of humanity, and shows us the negligible progress we made. Instead of moping about our stagnation as a species, however, Futurama opts to have a laugh. Departing from realism also allows for a more colorful cast of characters, better settings to draw jokes from, and more use of tactful history and pop culture. No one in the year 3000 is going to care about a movie star from a millennium ago.

American Dad is just straight up better than Family Guy. Characters in the former are actually well written rather than interchangeable narrative contrivances. Stan Smith may be a parody of conservatives, but he is not a strawman. Instead of being an extreme caricature, he has interests and motivations outside of far right politics. Even though Seth MacFarlane productions largely swing left, the writers on American Dad have (mostly) humanized the ultra-conservative Stan Smith by tying his beliefs back to relatable thoughts and emotions. Stan is not wrong because his values are stupid, but because there was a perspective he had not considered or a personal insight he had not reached.

American Dad! is also funnier and smarter, particularly because it got rid of Family Guy’s cutaway crutch. What were once fun non-sequiturs became the sole source of cheap giggles. Ending the obligatory segmentation of each episode helped the show create solid structure and consequently stronger jokes. Unlike Family Guy’s pitiful attempts to tackle serious issues a la “Screams of Silence” or “A Shot in the Dark,” American Dad! also put more effort toward dignifying the issues it wants to discuss. “The American Dad After School Special” and “A.T. The Abusive Terrestrial” show how American Dad! can skillfully portray sensitive issues when they choose.

American Dad! and Futurama demonstrate what happens when creative minds are not forced to drive their first good idea into the ground, either by the profit driven corporate entities of network television or the perpetually dissatisfied yet paradoxically demanding fanbase. Their fresh ideas get a new start, unhampered by their tenuous connection to their predecessors. More often than not, it also results in better creativity, as the artist does not feel the need to keep wringing vitality out of something they no longer feel passionate about.

#4 — The Boondocks

This entry definitely reflects a conflict of interest on my part. Though this show is not without criticism, I do not think I will be able to remain unbiased in my discussion. I can tell my audience that I am able to push my personal beliefs aside, but I doubt they will listen. I imagine many readers will believe I am giving this show special recognition because Aaron McGruder was a University of Maryland alumnus, and the temptation to celebrate the work of a fellow Terp is too great.

On a serious note, Adult Swim’s The Boondocks mixes far left political commentary with sharp humor in ways that most adult cartoons could only imagine. Aaron McGruder provides largely poignant and unrelenting criticism of the government, mainstream culture, white culture, and black culture. Subject matter ranged from tearing down superficial rappers to lambasting the injustices committed against the black community. Looking back, The Boondocks was, and has thus far been, one of the only well-known animations to positively portray anything close to black radical politics.

Yet with how brazenly leftist the subject material got, The Boondocks always remained accessible, fair, and hilarious. Drawing from a list of talented black actors and actresses, The Boondocks covered the entire emotional spectrum. John Witherspoon brings sharp comedy with Robert Freeman’s emphatic speech and personality. Regina King demonstrates her acting range through the voices of Riley and Huey Freeman. Riley is the defiant, smart-mouthed child, while Huey is the stoic, and highly intelligent one. The most iconic character is, however, Uncle Ruckus, an Uncle Tom archetype turned up to 11. His unabashed racism was always a source of antagonism and comedy.

The Boondocks is also known for its homages to renowned Japanese anime series, including Samurai Champloo, Trigun, and Cowboy Bebop. The Asian influence pairs well with the action and drama of The Boondocks, while the comedy makes it stand out from its inspirations. An adept purveyor of anime or other forms of Asian entertainment can draw even more value from the show. Season 3 Episode 4 “The Red Ball” was the most affectionate of parodies.

The reason this show is not higher on the list is the dismal fourth season. Even though Aaron McGruder left Adult Swim, the network still wanted to air one more season of The Boondocks. Audiences received an absolute mess. All of the scenarios felt half-baked, the jokes were weak, the writing was flaccid, and the character were all at their worst. Why did Adult Swim do this? In other countries, people lose hands for this kind of thievery and exploitation. Leave it to them to kill one of the best things that ever happened to their network.

#3 — Rick and Morty

The other best thing to happen to Adult Swim, at first glance, looked about as visually welcoming as a dead rat in a pumpkin pie, but Rick and Morty turned out to be one of the funniest and most profound animated series ever created for any network. The titular characters, Rick and Morty, are respectively an elderly genius scientist and his dopey teenage grandson. The show draws serious influence from Back to the Future, as evident by the animated short from Justin Roiland named Doc and Marty. Only instead of being a generic mad scientist, Rick suffers from serious alcoholism, which is something most people would do if they understood the totality of human existence in the way Rick does. He delays the impending existential crisis by focusing on science, indulging in hedonistic pleasures, and abusing his grandson.

Much like Futurama, this show stands out for its inspired science fiction settings. Rick and Morty travel between dimensions of the multiverse, explore the oddness in the depths of space, parody Inception to enter people’s dreams, and watch interdimensional cable programing. Morty’s mother and father, Beth and Jerry, and his sister, Summer, are the human backbone to Rick’s chaos. Rick’s relationship with Beth is particularly captivating/heart-breaking. Consequently, Beth is one of the more complex and well-written female characters in any television program, which is noteworthy considering the misogynistic practices alleged to go on within the Adults Swim network.

The constant freshness and the continually tangible stakes reinforce the solid writing. Rick’s extremely antisocial personality plays well off of his relatively normal family. Morty’s family coming to grips with the insurmountable insanity of the universe is the source of both excellent comedy and poignant drama. The improvised scripts leads to strong comedy as well, as Justin Roiland (the voice of Rick and Morty) can write jokes that flow within the scene organically. A skilled improviser (which Justin Roiland is) can use naturalistic dialogue to great comedic benefit. If a show is going to paint a bleak picture of the universe, it is better to have a laugh about it afterwards.

Rick and Morty, however, most surprised me with its drama and presentation of deeply philosophical themes. This show tackles several complicated topics, including the oppressive weight of loneliness, the fickle morality of killing, the importance of love, and men’s pathological fixation with penises. Even the obligatory “haha, laugh at my feminism strawman” episode came down heavily on men. It seemed to suggest that maybe women would not be so “annoying” if you men would stop being callous, violent and self-centered. It’s no bell hooks essay, but it really surprised with its nuance. Adult Swim was lucky to have a show like this fall into their lap.

#2 — BoJack Horseman

I would not blame anyone for believing that this show is unbearable from the start, as the first season left a lot to be desired. What at first seems like the standard template for adult cartoons does get better throughout the season, but it was still brought down by ham-fisted writing and a concept that took a while to hit its stride. Regardless, BoJack Horseman made a few things clear with its debut: the status quo means nothing, the choices you make do affect those around you, you are probably not a good person, and the happiness you seek may not be as fulfilling as you believe.

Luckily for the Netflix viewing public, BoJack Horseman stepped up its game and became one of the best animated shows out there. And with good reason. BoJack Horseman is an aging horse actor trying to rise to fame again after a long hiatus following his TV debut, a sitcom called “Horsin’ Around.” As a deconstruction of the family sitcom, BoJack Horseman lambasts the conventions of saccharine family shows by juxtaposing them with the harsh realities of network television, substance use disorders, familial strife, and the toxicity of fame.

As much of a taste for gloominess as I have, BoJack Horseman steps to the plate with great comedy. Hollywoo(d), a town of excess and shallowness, serves as a dynamic and colorful environment in which bored affluent people can bankroll ridiculous hijinks. The imagination and situational comedy taken from this gilded town rivals that of outright fantasy narratives. The writers also have their thumb on the pulse of technology and popular culture, making their observations of modern society feel less tired than the pedestrian jabs at selfies most comedians liberally dispense. The cast also consists anthropomorphized animals, who offer endless opportunities for visual puns.

There are so few shows like BoJack Horseman. It gets all of the good adjectives: funny, dramatic, brutal, honest, unflinching, and all of the other novelty-seeking buzz words people use to describe what they want all shows to be like. Netflix is the best version of what FXX and Adult Swim try to be: a broadcasting service with fewer restrictions and more creative freedom, willing to throw a bone to unique ideas that show promise. BoJack Horseman is not only a good show in its own right, but it is evidence that creative ideas can make it with the help of ambitious companies willing to support them. This show should not be missed.

Honorable Mentions:

South Park

I can respect the South Park’s influence on adult animation but only on a detached and objective level. Their humor is often 50/50 with me. Some episodes are genuinely clever and hilarious. Their satire of institutions, society and other media can be fun, and their boldness opened new doors for what comedy could talk about. At the same time, many of their jokes do not land with me. They have a habit of drawing out jokes for far too long, or saying taboo words in a silly voice and calling that a joke (“He was raped,” “She had an abortion,” “You’re a Jew,” “Something, something butthole”). It’s exasperating and tedious; like trying to talk to a kid who giggles every time you say chicken breast. I have to recognize the importance of South Park for adult animation, but my favorite thing about the show is how it paved the way for better programs.

The Simpsons

Now I said that deconstructing the family sitcom put distance between The Simpsons and me, but then I put BoJack Horseman as number two on the list. How did BoJack Horseman succeed when The Simpsons lost me? Bojack Horseman deconstructed the genre by creating captivating characters and strong interpersonal relationships, rather than exclusively subverting the tropes from shows that never mattered to me. It is also hard to go back and watch every episode of that cartoon behemoth, especially since most other adult cartoons have taken jokes to places more relatable to me. The Simpsons is a great show, and it deserves the respect it gets for pioneering quality adult animation, but it will never be as special to me as it was to the people who followed that family since the very beginning.

 Daria

Daria is one of my favorite animated programs of all time. The comedy is sharp, the characters are lovely, and the messages about high school and adolescence are timeless. It is funny how the best thing to come out of Beavis and Butthead was the secondary character strong enough to get her own spin-off. Say thank you to the handful of people at MTV who wanted strong women leads. Despite the commendations, Daria does not quite qualify as adult animation. On a superficial level, the show contains very little “adult” content. There is almost no blood or violence. The swearing is minimal, with only the occasional “bitch”, “bastard” or “God dammit”. The sexual content is sparse and even educational. On a fundamental level, however, Daria is a show about teenagers. Teens were the target audience, the characters related to teens, and the adults who watch do so to reminisce on their teen years. Adolescence, for many, is characterized by cynicism, detachment, and a disregard for the people around them. Daria justified that attitude, while explaining how and why it is important to grow out of it. Because teenagers were meant to get the most out of this show, it was not considered adult for this list.

And the best adult carton is…

#1 — Archer

While most of the choices on my list offer some philosophical or humanitarian drama in addition to the comedy, Archer manages to stand out solely on its humor. Imagined as James Bond meets Arrested Development, Archer follows the adventures of titular character, Sterling Archer, a secret agent for the espionage organization, ISIS (this show was written before the infamous terrorist group became a global force). On top of being the world’s most dangerous spy, Archer is an antisocial, substance dependent, emotionally unstable, womanizing narcissist.

He works with field agents Lana Kane and Ray Gillette, fumbling through missions and sometimes miraculously coming out on top. The cast also includes Mallory Archer, Archer’s abusive mother; Pam Poovey, the crass and tough human resources woman; Cyril Figgis, the geeky comptroller; Cheryl Tunt, the psychotic sadomasochist; and Krieger, the mad scientist. These colorful characters work in tandem with smartly written jokes to create exceptional comedy. Archer, the jerk, avoids being overbearing because the others can stand up to his presence.

The writing itself is unlike any other comedy. The humor blends clever (and less clever) wordplay, dramatic and situational irony, slapstick, misdirection, obscure historical references, equally obscure nods to geek culture, and “phrasing,” which always struck me as a more versatile and inclusive alternative to “That’s what she said.” The show takes this comic cocktail, bounces it off the well-developed personalities of their characters, and then drops it into imaginative settings. The world of espionage and spy-craft delivers a variety of otherwise serious situations for Archer to make farces of.

One additional standout in Archer is its comic anachronism. Technology, cultural references, and political figures are often stuck out of time, and the exact setting is a point of mockery within the show’s universe. This disparity helped Archer on the few moments of critical commentary. Although the writers are known for avoiding topics of global contention, Archer uses its anachronism to have the characters reenact the morally dubious actions of the government during the Cold War period. This includes assassinating world leaders, conducting government funded drug trades, and making secret deals with Russia. Through a sequence of blunders by ISIS, Archer mocks the recklessness of the government. Though seemingly overbearing when listed, the political criticism is so understated when done alongside Archer’s smart and fast-paced comedy.

Despite its initial lukewarm reception, the Emmy Award-winning Archer proved itself to be an unparalleled comedy. In its seventh season, this crew of spies/drug dealers/CIA operatives/ private security contractors/actors have still been going strong. This is an adult animated comedy masterpiece and one of the best programs on television.