A Brief History Of Hip-Hop On 'The Simpsons'

When 50 Cent, Ludacris and Cyrpress Hill hit Springfield.

Bart Simpson Rap

Image via Fox

Bart Simpson Rap

This week it was announced there’s going to be a hour-long hip-hop themed episode of The Simpsons, riffing on The Great Gatsby. It’s apparently going to be about Mr Burns making friends with a rap mogul, and feature a guest shot from Empire’s Taraji P. Henson. Obviously, The Simpsons hasn’t been at its best for over a decade now, so part of us is worried this could go horribly wrong. But on the other hand, we can’t not get excited about an all-hip-hop Simpsons special.

This won’t be the first time beats and rhymes have come to Springfield though. Over its 25-year life span, the show has featured cameos from the likes of 50 Cent, Ludacris and Cypress Hill, as well as Bart’s own short-lived rap career. Here are the key Simpsons hip-hop moments so far. 

Do The Bartman


Which episode: N/A (stand alone music video)

Oh, the days of early 90s novelty rap. Now that it’s a cultural institution, it’s easy to forget what an out-of-nowhere sensation The Simpsons’ first season was. Merchandise — both official and bootleg — flooded the shelves, and there was even a comedy single released. Normally these things are god-awful, but The Simpsons had an ace up its sleeve: Michael Jackson. MJ was a massive fan of the show, and wanted to ghostwrite a song for Bart. He was signed to a different record label, so his involvement was an open secret (he’s even name-checked in the lyrics), and while Nancy Cartwright is hardly Nas on the mike, it’s still a great pop tune.

Cypress Hill & The London Symphony Orchestra do ‘Insane In The Membrane’

View this video on YouTube


Which episode: “Homerpalooza”, season 7

The LA trio guested alongside Peter Frampton and Sonic Youth as acts on the fictional Hullabollaz Festival, where Homer is billed as ‘the man getting hit by a cannonball’. Probably too stoned to remember that they didn’t even book the world famous London Symphony Orchestra to play with them, they take them on nonetheless and it turns out they know how to play a decent version of ‘Insane in the Membrane’. If only we could hear the whole version.

Pranksta Rap ft. 50 Cent

The Simpsons 50 Cent

Luda Crest

View this video on YouTube


Which episode: “You Kent Always Say What You Want”, season 18

For their 400th episode they acquired the voice talents of one of ATL’s finest, Chris ‘Ludacris’ Bridges. The Dirty South MC makes his appearance in an awareness video about the importance of cleaning your teeth (as Luda-Crest). He does this by dropping bars and engaging in some physical violence on those ‘low-life degenerates’ Gum Disease and Tooth Decay. The highlight is Luda shooting toothpaste out of his head. Turns out that video was for a one-time showing in Canada only…

Which episode: “Gal of Constant Sorrow”, season 27 

When you’re 10 years old receiving a measly few dollars, or pounds, it’s a f***ing upgrade. The smart move would be to put the money into a piggy bank, but if you’re Bart Simpson you damn well know it’s about that ‘YOLO’ life. El Barto remakes his own version of Drake’s “Started From The Bottom” while throwing $1 bills in the air like they’re confetti and it goes really, really well. In fact it’s genius! Who says The Simpsons are losing the cultural relevancy? They must be out of their damn minds!

The “I Didn’t Do It” song

I Didn't Do It

Drederick Tatum enters the ring to Redman

Drederick Tatum

“A video christmas card from Tupac Shakur”

Krusty Kristmas

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