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On April 19, 1987, America was introduced to the most famous family television will ever know: The Simpsons.

Homer, Marge, Lisa, Bart and Maggie all made their first appearance on little short segments aired during the short-lived The Tracey Ullman Show.

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From there, The Simpsons would go on to make history. The animated show premiered as its own entity on December 17, 1989, and it instantly became one of the most popular shows on television. Now, 25 years later, it has made history as the longest running scripted TV show in history. 

Not too shabby.

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Over the years, The Simpsons have had numerous famous celebrities on their show, whether they’ve played him or herself or another character. There have also been a number of our favorite hip-pop stars, as well.

To celebrate 25 years of animated excellence, here is the 10 most memorable hip-pop appearances on The Simpsons over the last 25 years.

Michael Jackson – “Stark Raving Dad” (1991)

Areosmith “Flaming Moes” (1991)

Red Hot Chili Peppers – “Krusty Gets Kanceled (1993)

Barry White – “Whacking Day” (1993)

James Brown – “Bart’s Inner Child” (1993)

Cypress Hill – “Homerpalooza” (1996)

Blink 182 “Barting Over” (2003)

50 Cent “Pranksta Rap” (2005)

The White Stripes – “Jazzy and the Pussycats (2006)

Coldplay – “Million Dollar Maybe” (2010)

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