The Simpsons has been an American comedy institution for over thirty years. Over the course of 34 seasons, the show has hosted myriad cameos from celebrities of all walks of life. The most recent guest was Lizzo, who made her Springfield debut on the show’s 34th season finale.
From professional athletes to politicians, The Simpsons has shown no signs of stopping when it comes to working with famous folks. While Lizzo certainly made a splash with her appearance, she was by no means the first figure from the world of hip-hop to grace the show. Let’s look at some of the best cameos from rappers on The Simpsons.
6. Snoop Dogg, RZA & Common
A trio of rap iconoclasts made their debut on The Simpsons in 2017 during the show’s 28th season. Snoop Dogg, RZA, and Common were featured in “The Great Phatsby: Part Two.” The two-part episode centered around Mr. Burns seeking revenge on the rap mogul Jay G, voiced by Kevin Michael Richardson.
Mr. Burns, with help from Millhouse (Springfield’s local hip-hop head) attempted to produce a take down track against Jay G. Snoop, RZA, and Common were brought in help elevate the song. However, things didn’t shake out well for Springfield’s most famous miser. Jay G acquired a copy of the song before it could be performed, thus thwarting Burns’ plan.
5. Pharrell Williams
In the episode “Walking Big & Tall” it is revealed that several towns across the country have the same anthem as Springfield. It turned out that Hans Moleman was the former mayor of Springfield. During his tenure, he bought the song from a salesman who had also sold it to several cities. Moleman didn’t think it would be an issue since people from Springfield never traveled.
Lisa and Bart offer to compose a new anthem. However, in a hilarious cameo appearance, Pharrell Williams also proposes to write the song for Springfield. Of course, he was denied and banished from the town via being tied to a horse. Pharrell musically laments, “Shelbyville rules, Springfield drools!” as the horse gallops away.
4. Sir Mix-A-Lot
“Treehouse of Horror XVII” featured a trio of outstanding horror parodies. However, the most memorable segment was “Married to the Blob.” The tale centered around Homer becoming an insatiable, gelatinous monster and wreaking havoc on Springfield.
During his rampage, Homer gets a taste for eating heavy-set people. He hunts them down to a parody version of Sir Mix-A-Lot’s “Baby Got Back,” appropriately titled “Baby Likes Fat.” Sir Mix-A-Lot did not appear in the episode, but he did record the tongue-in-cheek track. It was the kind of self-parody The Simpsons has always been known for.
3. Cypress Hill
The first rappers ever to cameo on The Simpsons were the hip-hop trio, Cypress Hill. Way back in the season 7 episode “Homerpalooza,” the group appeared along side other musical acts like The Smashing Pumpkins and Sonic Youth. However, Cypress Hill had the best gag in the episode.
The rap group was featured backstage of the show’s fictitious music fest, Hullabalooza. Cypress Hill’s gag centered around ordering the London Symphony Orchestra while they were high. The result was a unique version of “Insane In the Brain” that even got Marge bobbing her head.
2. 50 Cent
In the season 16 episode “Pranksta Rap,” Bart found his passion for hip-hop and tried his hand at being an MC. Marge and Homer forbade Bart from attending a benefit rap concert called Murder 4 Life. Bart (being Bart) snuck out to attend the show and found himself on stage with his favorite rapper, Alcatraaaz.
After impressing Alcatraaaz with his rap skills, Bart was taken back home in the rapper’s Hummer limo. During the trip, none other than 50 Cent rolled up next to them. In a wonderful exchange, 50 Cent delivered some self-deprecating humor and admiration for the fledgling MC.
1. Ludacris
“You Kent Always Say What You Want” was an episode about rehabilitating anchorman Kent Brockman after an on-air gaffe. However, the cold open of the episode featured the absolute best rapper cameo The Simpsons has offered.
Ludacris appeared as an anthropomorphic tube of toothpaste named Luda-Crest in an informational dentistry video called “Menace Tooth Society.” Luda-Crest fights off various tooth diseases and raps about oral health. It was as baffling as it was hilarious. Shortly after the video, Ludacris appears again as himself, threatening a dentist with legal action. Of all the rappers who’ve made a cameo on The Simpsons, Ludacris’ appearance was by far the most memorable.