10) Kanye West– Cleveland show

Kanye makes an appearance on Family Guy spin-off The Cleveland show as Kenny West AKA the “Black Zak Efron”. He rap battles with Cleveland Jr. to show him why he should stay away from Kenny West’s girl. Papa Doc and B Rabbit have got nothing on this one as the two freestyle MC’s exchange some personal bars with a twist ending.

9) Eminem – Family Guy

Eminem gets a plug from Stewie for his album Relapse which was dropping at the time. Marshall then asks Stewie if he is a “Gay baby” It’s overall a pretty weird segment. Probably could have done some funnier stuff with Eminem and Family Guy, but Eminem had some bigger issues during his Relapse days

8) Ludacris/50 Cent – The Simpsons

Ludacris plays superhero “Luda Crest” in “Menace Tooth Society” and 50 cent plays himself. The latter drops knowledge on Bartholomew J. before heading off to pick up dog poop. There has been a ton of musical guest stars on The Simpsons with very few of them being from the hip hop genre. Hopefully we will see some more in the future.

7) Drake – The Lebrons

Drake and his boys roll up in matching OVO jackets to (somehow) help the kids by freestyling and using a grotesque amount of product placement. So Corny. So Drake.

6) GhostFace Killah – The Boondocks

The Wu-Tang General plays himself, sort of, in the Adult Swim sitcom The Boondocks. GFK voices the Ghost of Ghostface Killah who has come back to earth to warn Huey that his Granfather’s arch nemesis Stinkmeiner’s ghost is coming back to earth as well. The Boondocks is a hilarious show and could have a top 10 rappers list all on its own.

5) Tyler, The Creator & Childish Gambino – The Regular Show

Tyler, the Creator and Childish Gambino go at each other in a rap battle on The Regular Show. Due to copyright claims only this low quality version is available, but its still funny:

4) Beastie Boys – Futurama

Fry Bender and Leela go to check out some old, old, incredibley old school beats at a Beastie Boys concert in the future. Only the heads of the trio remain, but they have still got it busting mad rhymes at an 86% success rate. Despite how cool Fry was looking Ad-Rock was not that interested in meeting him backstage.

3) Kanye West – South Park

I am a big Kanye fan so this one was tough for me to rank so high… but it is just too damn funny. Kanye West the gay fish. The whole episode is a classic, if you have never seen it watch it immediately. One of the boys in town invents the funniest joke ever told and everyone in the wold gets it except for Kanye West. Amazing. The new episode with Kanye and Kim was not as good so I’m sticking with the original.

Do you like fish sticks?

2) Cypress Hill – The Simpsons

Cypress Hill on the Lollapalooza tour along with Sonic Youth, Smashing Pumpkins and Homer Simpson. There were so many classic moments in this episode but it can probably be summed up with this quote “Did anyone order a London Symphony Orchestra? Possibly while high? Cypress Hill, I’m looking in your direction”

1) Mos Def – The Boondocks

On the Boondocks Mos Def plays one of the funniest characters ever created in any TV show in my opinion, the rapper Gangstalicious. Gangstalicious is a closeted homo sexual rapper who is trying to make it in the hip-hop industry and the hints are dropped without any of his fans noticing is amazing.

Check out Gangstalicous’s music video “Homies over Hoes”