On 2005's "Old School Rules" by Danger Doom, Talib Kweli raps that, "I might be buggin but it seem to me/That cartoons be realer than reality TV." While we could easily enumerate a number of reasons why Kweli's lyric is a bold hyperbole to make - namely because they're cartoons - it definitely speaks to hip-hop's longstanding history with the animated arts. Whether it's Kid 'n Play's short-lived animated series or the Gorillaz actually being animated, hip-hop has been all over the map when it comes to cartoons.  Now, XXL has put together a list of 23 hilarious hip-hop moments in televised cartoon history.

Family Guy Translates The Wu-Tang Clan

Year: 2006

Peter Griffin pulls a Rap Genius on the Wu-Tang and gives a rough translation Inspectah Deck's verse from "Bring Da Ruckus." Seth MacFarlane and company get bonus points for referencing one of the Clan's deeper cuts.

South Park Makes Kanye West A "Gay Fish"

Year: 2009

South Park has a lot of amazing moments, but one of its best by far is From making Yeezy hump a giant fish to recreating the supreme ridiculousness of this photo, Trey Parker and Matt Stone achieved the impossible: rip on Kanye hard enough to make him laugh at himself.

The Boondocks Casts 50 Cent in Soul Plane 2

Year: 2007

Soul Plane is arguably one of the least funny and most surprisingly racist films ever made. However, it would have been amazing to witness "Air Marshall" 50 Cent take down terrorists...or die trying.

The Simpsons Creates "The Bartman"

Year: 1990

Although New Jack Swing has gone the way of the dinosaurs and snap music, "The Bartman" still gets love for its nostalgic value and significance in pop culture. But it's probably best not to break out Bart's signature moves at the club anytime soon.

The Cleveland Show Exposes The Hip-Hop Illuminati

Year: 2012

The Cleveland Show doesn't deserve many accolades - it's exceptionally awful even by spin-off standards - but in this once instances, it's writer got right. Convincing Kanye West, will.i.am, Nicki Minaj, ?uestlove and Bruno Mars to portray themselves as Illuminati members takes a lot of balls, and thankfully, the script backs up the hilarious conceit.

South Park Resurrects The Notorious B.I.G.

Year: 2006

Leave it to the geniuses behind South Park to bring Biggie back from the dead, only to pair him with Butters, the lamest character in the show. But if you think about it, Diddy already kind of did that with Born Again and Duets: The Final Chapter.

Tyler, The Creator Battles Himself On Regular Show

Year: 2012

Although many hip-hop heads may not recognize the show's name, Regular Show has become one of Cartoon Network's biggest and most genuinely funny cartoons in recent history. In an unexpected turn, the show brings out Tyler, the Creator - as well as Childish Gambino and MC Lyte - for a rap-centric episode.

Space Jam Enlists B-Real, Method Man, LL Cool J, Busta Rhymes & Coolio

Year: 1995

Despite being a kid's comedy and oversized Air Jordan XI ad, Space Jam produced one of the dopest crew collabs of the mid-'90s. As awesome as the collaboration is, it would've been nice to see Redman on that list instead of Coolio.

Snoop Dogg Battles Bob Barker On Robot Chicken

Year: 2007

As evidenced by Happy Gilmore, Bob Barker fighting people will never not be funny. Add Snoop Dogg to the mix in a battle over spading and neutering your pets, and it's comedy gold.

Eminem Checks In For Celebrity Death Match

Year: 2000

Sadly, the humor of the above clip hasn't held up in the decade since it aired. But my 12 year old self still has great memories of this epic claymation battle, as well as the Eminem lyric is spawned on "Scary Movies" with Royce Da 5'9."

Family Guy & The "Hang Nail Rap"

Year: 2001

Although Family Guy never really capitalizes on its hip-hop minded fan base that often, one of its earliest interactions with the genre finds them parodying shout rap with a music video about hang nails. 

Yelawolf Raps For Squidbillies

Year: 2012

As one of Adult Swim's more bizarre series, Squidbillies is definitely geared towards a select base of individuals with an "acquired taste" (ie. psychopaths that like watching redneck squids maim themselves). But the heads over at Adult Swim bridged the gap by having Yelawolf put his spin on the show's opening credits.

The Simpsons & 50 Cent

Year: 2005

At the height of his career, Fif was landing guest spots and acting roles with nearly every TV show out at the time. But his spot on The Simpsons takes the cake by forcing the G-Unit general to pick up dog poop.

Schoolly D Performs The Theme Song To Aqua Teen Hunger Force

Year: 2000

Philadelphia rap legend and arguably the first gangsta rapper ever Schoolly D performed the opening theme song to Aqua Teen Hunger Force from 2000 until 2010. Kind of a far cry from "P.S.K.," but it's definitely a good look for fans of the show.

The Boondocks Channels State Property

Year: 2010

State Property is possibly one of the most unintentionally hilarious entires to the hip-hop cinema lexicon, primarily because of Beanie Sigel's rampant use of the phrase, "Get down or lay down." So leave it to The Boondocks to bring it back in the best possible way when Riley Freeman goes head-to-head with a chocolate-slanging gangster.

Killer Mike Stars In Frisky Dingo

Year: 2008

Few rappers possess a real sense of comedic timing, but Killer Mike knocked it out the park with his featured role on Frisky Dingo. We just wish that the show's creative team had cast Mike in their latest acclaimed series, Archer

Kid 'n Play's Entire Series

Year: 1990

Kid 'n Play's eponymous cartoon series definitely predates any of the XXL editorial staff's memories by, but if it was anything like the above clip, it was probably awesome. It also marks the first time for a rap act to ever sign on to its own TV show - a feat that deserves some recognition.

"Freaknik: The Musical" Casts The Entirety Of Hip-Hop

Year: 2010

With a cast that includes T-Pain, Rick Ross, Lil Wayne, DJ Drama, Snoop Dogg, Cee-Lo, Lil Jon and comedians like Andy Samberg and Affion Crockett, "Freaknik: The Musical" was destined to be a hip-hop classic. What makes the cartoon special great, however, is that it pays homage to the actual Freaknik musical festival in Atlanta.

The Boondocks Blasts Soulja Boy DJ Vlad & The Whole Hip-Hop Industry

Year: 2010

If there's one clip that best sums up "The Boondocks'" satirical genius, it's this one. The show lampoons Soulja Boy and Ice-T's beef, DJ Vlad's questionable interview skills and the cornier aspects of the hip-hop industry in one fell swoop.

Family Guy Bumps Some Geto Boys

Year: 2008

Although clip is a direct reference to the film Office Space, it's great to see that the show's producers went far enough with the gag to fork over the royalty payments for the Geto Boys' classic gangsta track "Still."

Cypress Hill Finds A Lost Child On The Simpsons

Year: 1996

At its prime, The Simpsons was one of the funniest series on television, eclipsed only by its contemporary "Seinfeld." In this clip, the show brings out Cypress Hill to deliver a PSA at a Lollapalooza-esque festival about a lost child who may end up the property of Blockbuster.


MF DOOM Plays A Giraffe On Perfect Hair Forever

Year: 2004

On this short lived Adult Swim series, DOOM played the coolest talking giraffe since since Toys-R-Us' Geoffrey. Although the show didn't last terribly long, it did produce a song of the same name from Metal Fingerz and Danger Mouse's Danger Doom collab.

Jay-Z And Warren Buffet Team Up For A Cartoon

Year: 2011

Sounds like Hov's gotten better at delivering dialogue since State Property. Cartoons are supposed to be funny, but Hov and company seemingly achieved that goal without actually trying.

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