Whether collaborating with an artist or just spotlighting them, Cartoon Network's Adult Swim has brought us many musical moments over the years that are hilarious, heartfelt, and even artistically boundary-pushing. Creators at Adult Swim frequently come up with abstract and absurdist programming that addresses complicated topics, most of which tend not to pop up in cartoons: sex, feminism, violence, and strong language, to name a few. Put that to music from some of our favorite independent musicians, and these cartoons are brought into our reality, as if Rick & Morty were our quirky neighbors with complicated issues (and, oh yeah, they happen to listen to Elliott Smith).

Space Ghost Coast to Coast and Pavement

You can’t talk about the history of music on Adult Swim without addressing Space Ghost Coast to Coast, which aired on Cartoon Network before Adult Swim came into existence in 2001. The show’s quirky vibe, obscure jokes, and awkward animation-meets-live action interviews set the stage for what the Adult Swim brand would become. But Space Ghost Coast to Coast’s wildest musical moment has to be the star-filled episode featuring (now Dad Rock band) Pavement. In this 1997 episode, Space Ghost keeps introducing Pavement as “The Beatles” while the band jams at inopportune times, interrupting interviews with guests Colin Quinn, Red Green, Goldie Hawn, and Tommy Davidson.

Aqua Teen Hunger Force and MC Chris

Aqua Teen Hunger Force started working with musicians from day one, collaborating with Schoolly D to produce the show’s theme song. Schoolly D, who wrote the song in the back of the limo on the way to the recording studio, wouldn’t be the last artist to work with the ATHF producers. The show would have a multitude of other musicians grace their studios, but no musical guest is as memorable as MC Chris, who comes on the show five times.

Each time MC Chris’ character is reincarnated, he’s on an overly complicated mission that involves sending hidden messages to people listening to his songs. MC Chris’ first iteration is MC Pee Pants in 2002, a diaper-wearing spider who lures Meatwad and the ATHF neighbor Carl to an abandoned warehouse with a song written for the show called “I Want Candy.” The song’s cryptic message outlines the rapper’s mission to drill a hole to Hell and release demons who will help him operate a diet pill pyramid scheme. Honestly, it’s not that funny of a joke, but what’s important about MC Chris’ appearances is that they demonstrate ATHF’s dedication to its cult following. MC Chris’ guest spots are an inside joke that nurtures the relationship between the show's creators and its consistent viewers.

Metalocalypse and Dethklok

Because of metal’s many subgenres (death metal, heavy metal, doom metal, thrash metal, the list goes on forever), it’s rare for a metal band to gain a huge following these days. But Metalocalypse’s cartoon band, Dethklok, became so famous that the fake band, created by Brendon Small for the show, became a real touring band, releasing four successful albums under the William Street Record label (Adult Swim’s in-house record company). All of Dethklok’s songs are coupled with extreme scenes that play off the genre's brutal themes and mythical fantasy worlds. The 2007 song “Thunderhorse” was such a fan favorite that it inspired a Dethklok tribute band called Thunderhorse. It’s also worth noting that the song is a bonus track in the video game Guitar Hero II.

The Boondocks and Mos Def

In The Boondocks, a black family moves into a predominantly white suburb and has to balance its identity with the expectations of the neighbors. Mos Def’s character, Gangstalicious, appears so frequently that he gets his own subplot that parallels the theme of the entire show. Riley Freeman, who identifies himself as a young gangster, looks up to Gangstalicious, but as a rapper, Gangstalicious struggles to balance the expectations of the thug life with his true identity: being a closeted Black homosexual. Mos Def as Gangstalicious performs several original songs for the show, but 2008's “Homies Over Hoes” song takes gangsta culture to the extreme, satirizing its portrayal of women while suggesting homoerotic undertones.

Black Dynamite's “The Wizard of Watts”

By flipping scripts, taking real life situations and characters to their extremes, and mocking stereotypes, Black Dynamite is an absurdist blaxploitation TV show whose social commentary makes us reflect on our own world’s politics.

No episode challenges viewers more than the finale, “The Wizard of Watts.” Black Dynamite goes on staycation from being the vigilante hero of his hood, which sparks a riot that’s reminiscent of the L.A. Riots (and eerily timed because it aired in early 2015, not long after the police brutality in Ferguson). After getting hit in the head with a brick, Black Dynamite is transported to “The Magical Land of Oz-Watts” and has to navigate the world with special musical guests Tyler, the Creator, Erykah Badu, J.B. Smoove and Tim Blake Nelson.

The star-studded animated musical features original songs, including a soulful “You Can’t Pimp” performed by Erykah Badu, and a clever parody of “If I Only Had a Brain” that wrestles feminist themes by describing how life would be different if the Tin Bee “Only Had Some Balls."

Moral Orel and Mountain Goats

Some of Adult Swim’s most important musical moments aren’t direct collaborations, but in the form of a subtle nod through licensing. Moral Orel is one of Adult Swim’s darker shows, and its use of the Mountain Goats in Season 3 makes the show even more unsettling. At the end of a 2008 episode called “Numb,” the Mountain Goats' song "No Children" accompanies a point-of-view scene where the father exchanges glances between a glass of whiskey and the domesticated life he’s created for his family. The song poetically depicts the father’s alcoholism and makes the crumbling relationship between Moral Orel’s parents palpable and heart crushing.

Rick & Morty and Chaos Chaos

Rick Sanchez comes off as an overconfident, alcoholic, scientific genius who brings his family along on inter-dimensional missions to help calm their existential crises and angst. Viewers spend much of Season 1 believing Rick is a total narcissist and intergalactic know-it-all, but after Rick’s brief fling and traumatic breakup with Unity in Season 2’s “Auto Erotic Assimilation” (2015) we see that many of Rick’s quirks might be the result of deep-rooted depression. To the tune of Chaos Chaos’ “Do You Feel It,” Rick tries to end his life with one of his machines in the garage. The moment raises some complex feelings, and you can’t help but grow some compassion for a misunderstood character who seems as though he has control over the universe, but doesn’t have control over himself.

Freaknik: The Musical

There are too many rappers to count in this 2010 T-Pain produced animated special. Drawing inspiration from the actual Freaknik music festival in Atlanta, the story follows an amateur rap group, the Sweet Tea Mob, voiced by Young Cash, Rick Ross, and CeeLo Green. Along the way the crew finds some ladies, throws down at a frat party, and finds inspiration in a Jesus-like gangster voiced by Lil Wayne. Freaknik is one of Adult Swim’s largest collaborations, with rap performances by Rick Ross, Mack Maine, T-Pain, and Snoop Dogg. The music featured in the special was later released as a soundtrack by Jive Records and Nappy Boy Records.

Adult Swim Bumps: Flying Lotus and Danger Mouse

Adult Swim’s eclectic music is also highlighted through clever commercial interludes, or “bumps." Whether it's just music playing over a black screen with white text, or a full-on animated music video, the Adult Swim bumps have become important platforms for experimental and independent artists. One of the best Adult Swim bumps of all time is Flying Lotus' "Zodiac Shit" from 2010, a psychedelic animation of constantly shifting lines and patterns, perfect for zoning out in the wee morning hours.

Danger Mouse also contributed to the Adult Swim bumps. His involvement with the network led to him teaming up with MF Doom for the album The Mouse and the Mask (2005), which features characters from Aqua Teen Hunger Force, Harvey Birdman, Sealab 2021 and Space Ghost Coast to Coast. This collaboration inspired the founding of Adult Swim’s own in-house label William Street Records.

Off the Air

As Adult Swim approached its 10th anniversary in 2011, Dave Hughes, who previously worked for MTV Animation, felt that the network was moving away from its experimental roots. Hughes pitched the idea of intertwining archival footage and music with bizarre transitions into a type of mixtape played amongst the animated characters. This project became Off the Air, which plays during the 4 a.m. graveyard slot, featuring bands such as Handsome Furs, Death Grips, Black Moth Super Rainbow, Parquet Courts, and Liars. A whole special was even devoted to a 22-minute-long video (2013's Dan Deacon: U.S.A.) for Dan Deacon’s album America, as well as a video animated by nine different artists for his song “When I Was Dying” from the 2015 album Gliss Riffer.

Additional reporting by Jonathan Palmisano.