D'oh Boys: Every Simpsons-Rap Reference Ever

From 50 Cent to Drake, the internet's most complete list of Simpsons-rap on the internet.

[Editor's Note: We've updated this post with new Simpsons greatness including Rihanna, Drake and an interview with B-Real about Cypress Hill's appearance on the show.]

If I had my way in college, I would have double-majored in The Simpsons and hip-hop with a minor in napping. Before hip-hop came into my life, The Simpsons is what gave me purpose; Homer was like my other dad. Every Sunday, my family would get Chinese food and settle in at 8PM for the latest episode. Before I knew how to read a clock, when we would go on long car trips, my parents would tell me how much time we had left in relation to the length of a Simpsons episode. Shit, I even wrote my college essay about The Simpsons and it's safe to say I have seen every episode at least three times (up until like season 14 when it started to go south).

I have to admit though, aside from a few episodes here or there, it's been a while since The Simpsons played a big role in my life. With work, life, and you know, being a functional adult, finding the time to watch a cartoon not called Archer has been tough. Thankfully FXX has made it easier by showing a marathon of every Simpsons episode ever. Working from home has many benefits, and being able to have The Simpsons playing in the background has been one of them. It' been a long time since I've seen Homer lead the charge to get the Springfield lemon tree back or Bart play pee-wee football. So long in fact, that before I never really thought of The Simpsons through the eyes of a rap nerd. So, now that I am both a certified Simpsons ANDrap expert, I think it's time we take a look at times when the two have merged into one beautiful hodge-podge of my life influences.

Rappers on The Simpsons

As any fan knows, musical cameos are as integral to the Simpsons DNA as donuts and Ralph Wiggum quotes. Everyone from Aerosmith to ZZ Top has been a guest star; shit, they even had Michael Jackson voice a crazy guy who thought he was Michael Jackson! So the King of Pop has been a guest, but what about all our favorite rappers? Do they get any love from TV's favorite family? Kind of. There are a few emcees who have been Simpson-ized, but not as many as you might think. The lucky few are:

50 Cent plays himself: "Pranksta Rap" Season 16, Episode 9

Ludacris plays Luda-Crest: Season 18, Episode 22
If you want to hear him talk about it, check this out.

Sir-Mix-Alot performs"I Like Big Guts": Season 18, Episode 4

Cypress Hill: Season 7, Episode 24
"Someone ordered an orchestra, possibly while high... Cypress Hill I'm looking in your direction"

If you are interested, here is an extended, Simpsons remix of "Insane In The Membrane".

[Update: I had the chance to talk with B-Real last week, and I had to ask him about his appearance on The Simpsons. He told me the orchestra was entirely the writers idea and they were the ones who brought in an actual orchestra to record the new version of "Insane In The Membrane." Makes me appreciate the writers even more. They went all out for a small joke in one episode; details, details, details.]

Ice T (sort of): Season 5, Episode 11

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There are about a billion other musical guests, but none in the hip-hop hemisphere. Damn...really? Why is it that the two things I love so much can't be together more often? It's like Homer having to make Skittle Brau. I think it's because The Simpsons is old...like really fucking old. Nowadays, hip-hop is so embedded and ingrained in our culture, it's almost impossible to avoid, but you have to think, The Simpsons' peak was the mid 90's. That means it predates shit like Illmatic and the so called  "Rap Golden Age." Back then hip-hop was still largely considered a sub-culture, so it makes sense that The Simpsons may have ignored it. Although, The Simpsons have not been that hip-hop friendly, it hasn't stopped these rappers from dropping some Simpsons related bars. (no Moe's Tavern). Mmmmm.....bars.....

Rappers Reference The Simpsons

But the clear winner here is Bloodhound Gang. Okay, so they aren't exactly rappers, but they made an entire song entirely out of Ralph Wiggum quotes.

And while this last one isn't a reference per se, Masta Ace rapped over The Simpsons' theme song, further cementing his status as one of my Top 5

Because The Internet

So, The Simpsons may not be so intertwined with hip-hop, it hasn't stopped the internet from bringing them together. Honestly, not really sure how to set up these next few videos, just press play and praise the internet gods.

And for the man who has  everything...a motorized tie rack a clip of Mr. Burns crying synced with Wu-Tang's "Tearz":


Since this groundbreaking, Pulitzer-winning investigation was first published there have been some more instances of my two favorite things in the world colliding. And weirdly enough both happened recently. They aren't necessarily guest appearances - those are still surprisingly sparse - but they are definitely worth mentioning. 

First, to celebrate "Work" reaching number one on the Billboard Hot 100 Chart, Rihanna posted this to her Instagram. It's one lapdance Drake will happily sit out. 

The second instance comes from an actual episode. In "Gal of Constant Sorrow" (season 27, episode 14), when Drake's "Started From The Bottom" gets Bartman-ed. I went in expecting this to be kind of cringeworthy and hokey, but I actually thoroughly enjoyed it. Even in its twilight years The Simpsons still gets me from time to time. Your raps in an episode of The Simpsons? This must be a dream come true for Quentin Miller. 

Never in a million years did I think my job would entail writing about hip-hop and The Simpsons. At the same time. It's crazy to think about, but both have been with me through a large portion of my life. They've been a constant in my 25 years on this earth, and I don't see that changing anytime soon, especially if this marathon is like a yearly thing, or if FXX just becomes an all TheSimpsons channel (fingers crossed). This was a pleasure to write, but now, unfortunately, I am never allowed to complain about my job, even when it entails listening to Migos.

p.s. - I'm aware Kid Rock also made a cameo, but the day I consider him a rapper is the day I quit writing.

p.p.s. - This guy turned rappers into Simpsons characters. It's pretty dope

Lucas Garrison is a writer for DJBooth. His favorite album is “College Dropout,” but you can also tweet him your favorite Migos songs at @LucasDJBooth. Illustration by Olga Wójcik.



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