20 Years of ‘The Boondocks’: Iconic Cameos From Rappers & Comedians
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20 Years of ‘The Boondocks’: Iconic Cameos From Rappers & Comedians

2005 TCA - Turner
Source: L. Cohen / Getty

Can you believe it has been 20 years since the premiere of the series The Boondocks?

The Boondocks is an adult animated series created by Aaron McGruder that premiered on Adult Swim on Nov. 6, 2005. The highly controversial comedy show, which was based on McGruder’s comic strip of the same name, took risks in raunchy, dark yet conscious humor and was revered as one of the most unapologetic adult cartoons of its time. It also helped skyrocket Adult Swim as its own comedic platform in its own right.

The show was memorable for several hilarious yet controversial reasons. Like the episode “Pause” that depicted a parody of Tyler Perry Studios (which was actually banned from airing on television after it premiered), or where a teacher says the N-Word to Riley Freeman (played by Regina King), who was trying to relate to him, and the family decides to sue the school system. Or even just the main character, Uncle Ruckus, who is an anti-Black self-hating man who praises “White Jesus” and swears he has a disease called re-vitiligo that causes his skin to darken instead of lighten.

The show covered controversial topics such as racism, social class, and stereotypes, along with highlighting several moments in pop culture in a satirical way.

The show also had a star-studded cast of Regina King, John Witherspoon, Gary Anthony Williams, Cedric Yarbrough and more— the show also featured iconic cameos from rap artists, comedians and other Hollywood heavy-hitters.

So, for the 20th anniversary, we have compiled a list of guest stars you may have heard voiced on the popular adult cartoon.