Tearjerker: The Boondocks

  • This strip, being one of the very few times we ever see Huey cry. Especially given how vocally negative Huey is in other strips about the very things Caesar points, out the idea that he would happily accept them in order to see people he lost again is very poignant. And even more tragic, the strip is written in someone's memory, making it very clear that McGruder is using Huey to reflect his own feelings about a real life loss.
  • Uncle Ruckus's life as a whole: Having a cruel, abusive father traumatizing him so badly that he hates his own race to such an extent. This gets even worse in one episode where he founds an entire church based on getting black people to hate themselves. The man is so incredibly mentally broken that when he's told via DNA testing that he is "102% African with a 2% margin of error", he completely loses the will to live.
  • The ending of the episode Riley Wuz Here: Riley and his mad art teacher paint a mural of Granddad and his deceased wife Dorothy, referenced from a picture of their wedding day. It moves Granddad to tears.
    • What makes it even more heart-wrenching/heartwarming is Riley's teacher's soft Meaningful Echo being heard. Why don't we paint a picture of someone you love, someone who is no longer with us... Doesn't help that the teacher was probably one of the few people Riley got to be good friends with and probably got arrested for it.
    • Even worse is that the episode points out how pretty much nobody (including Grandad) believes in Riley up until he reveals himself, and that beforehand he's essentially squandering his talents to get attention from people including Grandad.
  • The entirety of "Good Times" deals with the issue of debt foreclosure. Robert Freeman owes millions of dollars on the house mortgage and throughout the episode the Freeman family has endure one humiliation after another as Eddie Wuncler, a competent sociopath, repeatedly harasses the family for the money. Robert has to, literally, sell himself into slavery to keep the house. The show reflects how brutal the housing market has become, how easy it is fall into debt with no safety net, and the lengths homeowners will debase themselves in order to keep a roof over their head for themselves and their family.
  • "Wingman" is a rather harsh lesson about how things can change, as well as stay the same. Grandad goes to a funeral for a friend he never liked, the guy constantly insulted him, almost got him shot out of the sky in WWII, and was just a terrible person; Huey, on the other hand reunites with one of his best friends, who already has moved on, and pushes the fact that Huey moved away in his face. After both, in their own ways, get the courage to be the better men and make amends, Grandad's friend (post-humorously{pun not intended}) sends a final disrespectful insult he disguised as something nice to him, and Huey tries to apologize for a fight he started with his friend, only to get a bloody nose. the Bittersweet Ending, which highlights Huey does have a friend he didn't consider and implies that Grandad has actually forgiven Mo' despite everything else, lessens the blow.
  • "Passion of Reverend Ruckus" pushes so many of the main characters into awkward and hopeless situations, what with Grandad trying to stop Ruckus's Religion with one of his friends being lulled into it, and Huey trying as hard as he can to save a truly innocent man for charges that made no sense. The situation is so humongously large it makes Huey pray and cry until a Deus ex Machina miracle saves everyone.
  • Occasionally, episodes go out of their way to highlight Grandad's whipping, the beginning of "Smokin' With Cigarettes" comes to mind. Suddenly what's implied makes Riley's situation extremely depressing and sad.
  • After Kardashia's behind exploded and the frankly hilarious reason for her hospitalization, theres something rather sad about her last moments. Dying as everyone else discovers she wasn't a real Kardashian to begin with:
    Kardashia:...I just wanted to be on TV...