9 of Rap’s Most Memorable Animated Moments

From distinctly early-’90s curio MC Skat Cat to “South Park” spoofing Kendrick just last night, hip-hop and animation go way back. As rappers have become fixtures across the cartoon world, animation has yielded stylistically wide-ranging clips like Kanye West’s “Heartless,” Killer Mike’s “Reagan,” and Jay-Z’s “The Story of O.J.” Cartoon characters are constantly rapping too, often across from real-life rappers making cameos. A search for “Rap AMV” (animated music video) on YouTube produces thousands of fan-made clips, where cartoon fight sequences are soundtracked by mainstream and obscure hip-hop alike. Rarely do such dissimilar mediums become so prolifically linked, bonding over their shared young audiences and an appreciation for absurd, over-the-top personalities.

Because they meet so often, there’s no shortage of bad rap animation—crude, overly juvenile, cheesy. FX’s short-lived animated sitcom “Chozen,” about a gay white gangsta rapper trying to rehabilitate his image after being released from prison, was flat and offensive, barely scratching the surface of both its premise and its animated potential. Back in 1990, Marvel and Saban produced an animated series about rap duo Kid ‘n Play; while Kool Moe Dee, Salt ‘n Pepa, and MC Lyte made appearances, the NBC cartoon had very little to offer outside of its superficial relationship to its characters—which Kid ‘n Play didn’t even voice. Both shows only ran for a single season. “The Simpsons” has tackled rap on several occasions during its run, and while some episodes work better than others, their most recent attempt (a rap Great Gatsby mashup) speaks to their level of cheesiness in this department.

That said, the most impressive examples of rap animation can make you reconsider certain aspects of hip-hop itself. They’re wacky or ribbing, making light of rap self-seriousness or critiquing its mechanics. They stretch rap grandiosity far beyond its real-life limits, as an act of satire or hyperbole. In rare instances, it even test the limits of the art form, reimagining what rap can do.

Below is a mix of both—simply, some of the more memorable times hip-hop got animated.

MC Hammer’s “Hammerman” (1991)

Rappers often envision themselves as larger-than-life characters, but MC Hammer took the next step and made himself into an actual cartoon superhero. The short-lived ABC animated series “Hammerman” followed Stanley Burrell, a youth center worker whose magic dancing shoes transform him into the eponymous hero. Hammerman donned gold chains and those signature parachute pants to tackle sensitive social issues that his alter ego couldn’t. For all of the show’s corniness and after-school special energy, there was something slightly endearing about the dance-rap star using the power of Hammer Time for good.

“PaRappa the Rapper” (1997)

In the late ’90s, the small Japanese video game company NanaOn-Sha broke through in American markets with “PaRappa the Rapper,” which later became an anime series. The game’s titular star PaRappa, a thin rapping dog in a beanie, learns kung fu to impress his dream girl, Sunny Funny. Gameplay revolves around pressing buttons in rhythm with PaRappa’s punches and chops—a simple concept, no doubt, yet PaRappa remains a huge part of animated rap lore as the first and only crossover of its kind. PaRappa has appeared in sketches for the stop-motion sketch comedy “Robot Chicken” (once alongside 50 Cent) and still frustrates gamers two decades later.

“Samurai Champloo” (2004)

Shinichirō Watanabe’s anime series “Samurai Champloo” reimagined Edo-era Japan as a hip-hop period piece, marrying the free-spirited rap world with ritual-driven samurai culture. The show’s characters reflect this balance: Mugen is an unorthodox, B-boying swordsman while Jin is a hardlining traditionalist, and they’re forced to team up to achieve a common goal. Break dancing, beatboxing, and graffiti are set against the backdrop of historic Japan. Japanese rappers and producers like the late Nujabes, Fat Jon, and Tsutchie (of the rap trio Shakkazombie) brought texture to this world through their original music. The well-executed concept was daring, a feat of imagination further proving the value of cultural exchange.

Thugnificent from “The Boondocks” (2005–2014)

Aaron McGruder’s comic strip turned animated series “The Boondocks” had a close relationship with rap dating back to its time in the funny pages, and its move to the small screen in 2005 only strengthened those ties. One of its two main characters, Riley Freeman, was an avid fan who emulated the genre’s gestures and fads. An entire season-two episode focused on him becoming an honorary member of Lethal Interjection rap crew, only to get his brand-new chain snatched. Ghostface Killah and Xzibit made cameos as themselves. Yasiin Bey, Snoop Dogg, and Busta Rhymes all appeared on the show as fictional rappers. Lil Wayne was on the voice cast for “Invasion of the Katrinians.” But the best Boondocks rap moments come from recurring character Thugnificent, who goes into debt when his record sales decline and eventually becomes the Freeman’s neighborhood deliveryman. Thugnificent is a caricature mocking rap tropes, but he’s also a nuanced look at the world through the lens of a hip-hop head.

“Class of 3000” (2006–2008)

Andre 3000’s “Class of 3000” follows a famed jazz musician named Sunny Bridges (a nod to jazz legend Sonny Rollins), who quits the biz hoping that his new teaching job will repair his personal relationship with music. He ends up using music to teach his students about the world, often via the 29 genre-spanning songs the Outkast rapper provided. The Cartoon Network series could lean heavy-handed in its imagery (like portraying record execs as snakes), but it could also be every bit as charming as its creator. Though Andre’s qualms with the industry served as strong inspiration, “Class of 3000” initially was conceived as an animated version of The Love Below, his half of Outkast’s classic 2003 double album. “The show was originally supposed to be an Adult Swim show,” Andre told The Undefeated earlier this year. “It was going to be more edgy. But I felt The Love Below was its own entity. I wanted to create something new.”

“Afro Samurai” (2007)

Inspired by A Tribe Called Quest, De La Soul, and J Dilla, manga artist Takashi Okazaki wrote and drew “Afro Samurai,” the story of a black samurai’s quest to avenge his father’s death. The anime, starring Samuel L. Jackson as the titular character and airing stateside on Spike, makes evident its hip-hop influence through RZA’s score and theme song. Okazaki said that had he won the Emmy he was up for, he would’ve used his stage time to pay tribute to the late ODB (and hip-hop culture at large): “Years ago, Ol’ Dirty Bastard from the Wu-Tang Clan got up on stage to give a speech—even though he hadn’t won the award,” he told Japan Today. “And I remember him saying, ‘Wu-Tang for kids!’ So if I’d had the chance, I would have shouted out ‘Afro for kids!’ That would have been perfect.”

“Regular Show” — “Rap It Up” (2011)

Cartoon Network’s long-running animated sitcom “Regular Show” scored an early highlight with the season-three episode “Rap It Up,” which focuses entirely on a goofy rap battle between mismatched adversaries. A squeaky-voiced and lollipop-headed gentleman, Pops gets mixed up in a rap battle with famed rap battle group CrewCrew after they criticize his poetry. Pops finds rap rude and attempts to recite his poetry in battle, to dismal results. The CrewCrew, voiced by Tyler, the Creator, MC Lyte, and Childish Gambino, make as kooky a trio as they seem, and the whole episode treats rap battling as epic hijinks.

Freaknik: The Musical (2010)

During spring break in ’80s and ’90s, students from historically black colleges and universities would throw an annual street party called Freaknik, including celebrity guests, a basketball tournament, rap cyphers, and even a daylong job fair. The crowds continued to grow in size each year, eventually disrupting day-to-day life in Atlanta, and the event was banned in 2010. In Adult Swim’s Freaknik: The Musical, a group of teenage rappers summon the ghost of Freaknik, hoping to revitalize the city and win “a lifetime supply of money, clothes, and hoes.” The hour-long special is a bizarro monument to Atlanta rap culture, starring local institutions Big Boi, CeeLo Green, and Lil Jon, as well as T-Pain, Rick Ross, Snoop Dogg, Lil Wayne, DJ Pooh, and DJ Drama. (Adult Swim is streaming Freaknik: The Musical in full here.)

Captain Murphy (2012–Present)

During the summer of 2012, there was a race to expose the bassy voice behind the mysterious Captain Murphy persona, a cartoon rap villain named after a character from the Adult Swim cartoon “Sealab 2021.” After early speculation pointed to an Odd Future affiliation, Captain Murphy was eventually unmasked as an alter ego of Flying Lotus. The character’s reveal was closely tied to animation: there was a video of the Captain Murphy origin story, and an Adult Swim–premiered short film mixtape called Duality, which spliced random footage with 3D renderings of Homer Simpson and other cartoons. Even though the rapping was a bit rough around the edges (and the persona even moreso), the very idea of a “cartoon rapper” challenged pre-existing notions of rap “realness.” Murphy also played into FlyLo’s fascination with animation as a highly visceral extension of sound, as seen in videos like “Putty Boy Strut” and “Zodiac Shit.”