On April 19, 1987, The Simpsons premiered as a short cartoon on The Tracey Ullman Show.

It’s hard to imagine anyone predicting that the animated sitcom would become the longest running prime time TV series of all time!

If there’s one thing we love about The Simpsons, it’s the celebrity cameos.

Check out these eight times that some of our favorite hip-hop artists were featured on the show . . . But have a look at that Simpsons debut TV appearance first!

50 Cent

Season 16/Episode 9 – “Pranksta Rap”

Bart sneaks out of the house to attend a concert featuring hip-hop artist “Alcatraaz”. After defeating Alcatraaz in a rap battle, Bart Simpson meets 50 Cent on his way home!

Tupac

Season 24/Episode 19 – “Whiskey Business”

Tupac’s hologram actually makes the appearance on this episode! The video below has bonus content of every time Tupac’s name had been mentioned on The Simpsons!

Ludacris

Season 18/Episode 22 – “You Kent Always Say What You Want”

“Luda Crest” appears in an informational video Lisa watches while at the dentist’s office called “Menace Tooth Society.”

Common, RZA, Snoop Dogg

Season 28/Episodes 12 & 13 – “The Great Phatsby Parts 1 & 2″

In the two-part, hip-hop-themed, Great Gatsby-inspired episodes, Common, RZA and Snoop Dogg play themselves! Original songs for the episode were created by Jim Beanz, a producer on Fox’s hip-hop drama Empire.

Sir Mix-A-Lot

Season 18/Episode 4 – “Treehouse Of Horror XVII”

Sir Mix-A-Lot makes a cameo in audio form on The Simpsons annual Halloween episode. He reworks his classic hit “Baby Got Back” into “I Like Big Guts,” which celebrates the joy of being plump while an overgrown Homer Simpson terrorizes the town!

Pharell Williams

Season 26/Episode 13 – “Walking Big & Tall” 

Pharrell offers to write a city anthem for Springfield!

Cypress Hill

Season 7/Episode 24 – “Homerpalooza”

Homer, in an attempt to prove to Bart and Lisa how cool he is, takes them to a music festival featuring Cypress Hill, Smashing Pumpkins and more!