Aaron McGruder's The Boondocks deserves to sit in the pantheon of Black entertainment. Not many series—animated or live-action—nailed its subject as perfect as The Boondocks did, and as the years go by, we continue to see how impactful (and important) this series was.
As many know, The Boondocks started out in 1996 as a comic strip written and drawn by McGruder (and a small team of like-minded individuals). The show spent the next ten years gaining popularity, newspaper syndication, and causing controversy for McGruder's satirical voice, all filtered through three characters: Granddad, an older black man who saw the civil rights movement and is just trying to live in the suburbs with his two grandsons, Riley (the hip-hop-obsessed wannabe thug) and Huey (essentially, Boots Riley from The Coup)—although it further expanded its universe to include "Uncle Tom" (who was actually named Tom), a black guy who hates black people, a biracial girl who was confused af, and so many believable portrayals of the everyday black people we meet. Never afraid to skewer everything from social issues to the state of hip-hop, when word got out that McGruder selling the rights to The Boondocks for an animated show on adult swim, it was wildly known that it was going to be "that show." We'd lost Chappelle's Show in 2005, and were missing the informed voice on all of the fuckery facing black lives in America.
See, The Boondocks as a cartoon could do what shows like In Living Color couldn't: it was able to say things about current events and long-known struggles and situations in black America that some shows couldn't (although Dave Chappelle definitely got the closest). It covered issues like soul food, the war in Iraq, homophobia, "nigga moments," slavery, and so much more in ways that were as witty as they were real, in an anime style that allowed for some truly memorable sequences.
While it's a goddamn shame that a) McGruder left after three seasons of the show and b) the fourth season left a meh taste in the mouths of many, The Boondocks goes down in history as one of the realest shows about the black experience in America, even if its just a bunch anime(-influenced) characters spitting foul language and getting into fuckery. Complex's Boondocks consortium put their collective heads together and paired down the show's history into the 15 best episodes of The Boondocks, which you can stream on HBO Max (well all of the episodes except for "The Story of Jimmy Rebel", which was recently removed from the service).