Credit: Sony Pictures Television

Every Episode of ‘The Boondocks,’ Ranked

Twenty-five years ago, Aaron McGruder introduced the world to the Freemans, and nothing would ever be the same

Peter A. Berry
Published in
28 min readFeb 8, 2021

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The Boondocks started out as a fallback plan.

Before creating the comic strip, Aaron McGruder was a semi-aimless University of Maryland student who didn’t expect to graduate; instead, he wanted to be a comic book artist for Marvel. After realizing that his drawing skills weren’t up to par and that he’d lose his scholarship if he didn’t return to school, he’d loaded up on so many Afro American Studies courses that it was an obvious discipline to declare as his major. From there, he began to cultivate his defining work, one guided in part by his curriculum.

The Boondocks debuted on Hitlist.com on Feb. 8, 1996 before appearing in McGruder’s college newspaper, The Diamondback, later that same year. It eventually ran in The Source, too. The strip focused on the exploits of two elementary schoolers — a Black militant named Huey and his gangsta rap automaton little brother, Riley — and their grandfather, former Civil Rights era activist Robert Jebediah Freeman (affectionately known as Granddad). The three moved from the South Side of Chicago to the white-fenced fictional Woodcrest neighborhood after Robert decided he wanted to retire in peace, away from the dangers of the Chi. The only problem is that peace can be subjective, and assimilation, especially for Huey and Riley, can be even harder than it sounds.

When they first arrive in Woodcrest, Huey thinks he’s spotted late racist politician Bull Connor; it’s actually just a White guy washing his car. Riley is disgusted by the smell of the new town, but Huey tells him it’s just clean air. Their struggle to mesh with their new locale establishes the comedic fulcrum of the strip, one derived in part from the experiences of people like McGruder himself, who knew all too well “the intimidation of being one of two or three Black faces in a sea of faces that don’t look like you.”

With quippy one-liners and unfiltered commentary on race, rap, and American politics, The Boondocks was a comic strip…

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Peter A. Berry
LEVEL
Writer for

Peter is a writer and editor from the New York area. He’s written for XXL, Complex, OkayPlayer, Level, Billboard, Netflix and more.