The Top Five Rap Cameos on The Simpsons

Kid Rock!

​The squeaky-pitched funk of "Do the Bartman" might not come up often when rap nerds talk about hip-hop's golden era, but during The Simpsons' near-500-episode reign, the show has proved more than willing to spoof the rap world's biggest stars. So with the somewhat curious news that Nancy Cartwright, the voice behind pint-size jape-master Bart Simpson, will be joining Bay Area rappers Tajai, Casual, and Zion I, and making a guest appearance at the Hip-Hop Chess Federation's Spring Classic tournament in San Jose this Saturday, here the show's five most, uh, animated rap cameos.

5. Cypress Hill

In an episode that also features Sonic Youth and Smashing Pumpkins performing at the Hullabalooza music festival, perennial rap tokers Cypress Hill take to the stage with the expansive London Symphony Orchestra. It's a collaboration facilitated by the West Coast crew's love of a pungent puff. Backstage, a tech guy ponders: "Who is playing with the London Symphony Orchestra? Come on, people, somebody ordered the London Symphony Orchestra -- possibly while high. Cypress Hill, I'm looking in your general direction."

4. Sir Mix-a-Lot

Proving that he doesn't discriminate when it comes to packing on the extra pounds, Sir Mix-a-Lot flips his rump-shaking anthem "Baby Got Back" into an ode to the excesses of the gut -- ostensibly to soundtrack a "Treehouse of Horror" segment starring a humongous Homer. "I eat fat people for days/Like potato chips by Lay's," he raps indulgently.