This past Sunday, August 15th, 2010, television audiences across the nation said goodbye to what had quietly over the past five years become a cultural phenomenon. “The Boondocks” series finale marked the end of three seasons of biting humor, razor sharp social satire, and a poignant narration of hip-hop culture dominating a world that fears it. Not since “The Fresh Prince of Bel-Air” had audiences seen such a clear presentation of hip-hop’s influence on mainstream society, one that’s all the more pressing with the culture’s current prominence throughout all forms of media. The Boondocks captured effortlessly the tensions, conflicts and contradictions that plague hip-hop’s presence in the mainstream spotlight, while simultaneously celebrating the culture as deeply and personally as all true fans do. This was most evident in the show’s soundtrack, which featured both original music scored by musical contributors Asheru and 9th Wonder and classic cuts handpicked by the show’s staff. Couple this with the fantastic “Hip-Hop Docktrine” mixtape series and the dozens of collaborations with artists on and off air, and The Boondocks stands as one of the most significant television shows in hip-hop history. A look at a few key moments in The Boondocks’ soundtrack reveals just how well the series used hip-hop to craft narratives, develop characters and make prevalent arguments about the state of the music and the culture altogether.

The Boondocks is a character driven show, retaining the heavy focus on personality nuances and relationships between family that made the comic strip so infectious. When the strip was adapted for television, fans were excited to see the fuller development of characters who now had room to flex their personas beyond three panels of black and white. Huey is hands down the most complex character in the series, and his manifestation on screen portrayed him as a solemn, imaginative cynic with a sharp tongue and wisdom beyond his years. It only made sense then that during one of our earliest displays of Huey’s imagination, his nightmare about a fight with the Blind Nigga Samurai in the episode “Granddad’s Fight,” he is placed against the cryptic keys of the RZA and the Wu-Tang Clan through the album cut “Guillotine (Swordz)” from Raekwon’s Only Built 4 Cuban Linx… The fight scene (watch here) plays out in a dark jungle with Huey battling the Samurai under moonlight and Inspectah Deck rhyming in the background. The implications of this scene are in many ways obvious: the entire Clan are known kung-fu flick aficionados, and Huey’s infatuation with martial arts is a central theme of the series. But this track selection speaks even more directly to the conflict between Huey and the Blind Nigga Samurai, and ultimately between Stinkmeaner and Granddad.

During the fight, Huey struggles with the Samurai, complaining that he’s helpless against this constant opposition and yet can’t understand his motive. The harder Huey fights, the more he plays into the Samurai’s hands. At the end of Huey’s dream the Samurai yells out “What’s good nigga?! What’s really good?!” in a furious drawl that becomes Stinkmeaner’s calling card. That same blind, irrational aggression that Stinkmeaner embodies is echoed throughout “Guillotine”. The track makes several references to large battles and wars, but identifies no enemy or motive. It opens with the declaration that “it’s the Inspectah Deck on the warpath!” and he continues with the warning to “Run fast, here comes the verbal assaulter!” but offers no reason for the war or the assault. Deck’s verse is in direct conversation with Huey’s narration, as Huey notes that “he has no just cause to want my life. There is no forethought, no logic in his actions.” “He” here becomes both Inspectah and The Samurai. By pairing Deck’s verse with Huey’s narration within a nightmare representing the most frightening parts of Huey’s subconscious, The Boondocks staff sets up a sonic representation of the struggle occurring physically on screen, and mentally throughout the episode. Granddad struggles to apply reason to his conflict with Stinkmeaner (a simple fender-bender quickly becomes physical as Stinkmeaner tests Grandad’s ego), but his ability to see the situation for how miniscule it is makes him appear weak. As Huey phrases it, Granddad’s “sight” becomes “a liability.” A simple song choice becomes a symbol for an entire character and story arc here in one of The Boondocks’ true strokes of musical genius.

But The Boondocks aren’t all about war, and some of their greatest musical achievements have been about love. In “Riley Wuz Here,” Riley takes up painting graffiti on houses and enlists the help of a professional artist to pull off his biggest project yet. Throughout the episode, Riley’s public art is celebrated, but residents of the neighborhood refuse to believe that a child so young and seemingly uneducated could produce art so powerful. Riley struggles with this conflict as he wants to be recognized for his art but not suffer the punishments for its illegality. In the episode’s closing scene (watch here), Riley and his instructor are putting finishing touches on his final piece when the cops discover them and they are forced to flee. The backdrop for this car-chase is the classic psychedelic jazz record “Today” by Tom Scott. The chase is juxtaposed against Granddad and the neighborhood’s discovery of the piece, which is revealed to be a portrait of Granddad and his late unnamed wife on their wedding day. The scene is rich with subtle commentary on the relationship between the hip-hop generation and its predecessors who grew up on jazz and soul. The significance of this song choice isn’t the record itself, it’s that this song was sampled to create possibly the most iconic song in hip-hop, “T.R.O.Y (They Reminisce Over You)” by Pete Rock & CL Smooth. By choosing the original sample instead of CL’s version, the point hits even harder: “Today” now stands as an audible yoke between the jazz era of the 60s, Granddad’s time, and the hip-hop generation birthed in the 90s, which Riley is a direct product of.

Throughout the episode, Riley is repeatedly frustrated with his inability to express exactly what he wants to through his medium, and he only gets it right when he embraces the significance of the generation before him. His presentation of his grandparents’ love becomes a reflection of his own for them, as the appropriation of Tom Scott’s work by Pete and CL to express themselves becomes a celebration of both the past generation and the beauty of their own. Riley’s difficulties in validating his artistic voice mirror those of Pete Rock and producers like him who have fought for years to have their work respected as true art and not simply copyright infringement. This parallel is only enriched by the fact that “T.R.O.Y” is a tribute from CL to his grandfather, who “took me from a boy to a man, so I always had a father when my biological didn’t bother,” a sentiment that Riley would surely identify with. In the scene, the horn riff sampled in “T.R.O.Y” coincides with the image of the portrait, creating a moment so poignant that it’s difficult to not get the chills watching it. Here, The Boondocks seamlessly crafts a commentary on generational conflicts and the beauty that comes when youth culture and its predecessors embrace one another. They cap it with the perfect amount of hip-hop-savvy humor, as Granddad quickly demands “That’s it, no more memories. Clean it up… Nobody told you to paint all over my house cuz you wanna make a point, this ain’t ‘Beat Street!’”

Moments like these throughout the series are too frequent to cover in total here. It is The Boondocks’ relentless confidence in hip-hop to express these complex messages that make it so special. The show doesn’t dumb down for its audience; contrarily, it demands of them the insight to catch the allusions and make the connections necessary to get all that the show has to offer. It takes an art that has been for years refused as a relevant piece of culture and builds with it, making more than one ever thought imaginable before. Its dedication to staying almost shockingly current and consistently relevant will make it a sorely missed barometer for the state of hip-hop culture. For now, however, we can only hope that as its finale suggested, the crew is just pulling a Jay-Z fake retirement, and plans to come back after a couple of months. Knowing their history, we wouldn’t be surprised.