Tear Jerker / The Boondocks

"Why? WHYYYY?!"

Comics

• 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 that 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.
• One Sunday strip features Jazmine crying while Huey is trying to read. How does he respond? By yelling at her to stop!
• There are times when Huey can question his character and judgement, which can make us see how insecure he truly is. In one strip, he feels like he hasn't really made much of a difference in the world and actually feels useless, because he complains all the time.
• During the April 2000 arc, Huey is in a particularly worse mood than usual (after nobody reads his paper on Santa Claus) and everyone tries to make him feel better, only for him to keep saying that he hates everyone. It is only when Caesar shows up, he seems to brighten up a bit.
• Jazmine makes Huey a Valentine's Day card, but he just leaves her outside for hours and then tells her to go home.

Season 1

Return of the King

• The whole episode really, even if it was just an Alternate History that was entirely imagined by Huey.
  • Martin Luther King Jr. survives the 1968 shooting that killed him in real life, but falls into a 32-year-long coma. When he awakens to see the new millennium, he feels that he's now become irrelevant and out-of-place in today's society. His reputation takes a big hit when he sticks to his pacifistic ideals after 9/11, which causes Fox News to brand him as a cowardly traitor.
  • Later on, King is greatly disappointed by the embarrassing behavior of the younger generation of African-Americans, which eventually results in him experiencing an angry meltdown, and then calling them out for their foolishness. He resolves to move out and settle down in Canada, dying as a bitter and cynical Grumpy Old Man.

Riley Wuz Here

• Also a very heartwarming moment: Riley and his mad art teacher paint a mural of a happily married black couple, referenced from a picture of their wedding day. It moves Granddad to tears.^note It's not known who the couple is, but fans have chalked it up as either a young Granddad and his wife, or Huey and Riley's parents
  • 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 Granddad) believes in Riley up until he reveals himself, and that beforehand he's essentially squandering his talents to get attention from people including Granddad.
  • And setting the tone is the song playing during the reveal: Today.

Wingmen

• This episode is a rather harsh lesson about how things can change, as well as stay the same. "Sometimes, your friends aren't always as loyal as you want them to be."
  • Granddad goes to a funeral for Moe Jackson, a friend whom he never really liked; the guy constantly insulted him, almost got him shot out of the sky in WWII, and was just a terrible person overall.
  • Huey on the other hand reunites with Cairo, one of his former friends; who has already forgotten him, as he believes that Huey left him behind on purpose. Their arguing leads to a fight.
  • After both Granddad and Huey get the courage to be the better men and make amends, Moe (posthumously) sends a final disrespectful insult that he disguised as something nice to him; and Huey tries to apologize for the fight he started with Cairo, only to get rejected with a headbutt that gives him a bloody nose.
  • The Bittersweet Ending, which highlights that Huey still has Jazmine, his current best friend; and it implies that Granddad has actually forgiven Moe despite everything else, which lessens the blow.

The Block Is Hot

• Huey tries as hard as he can to get Jazmine out of her contract with Ed Wuncler I, who is fiendishly profiting from a little girl's labor without rewarding her.
  • It's pretty minor, but when Jazmine snaps at him and tells him to go away, Huey actually seems genuinely sad. Despite his personality, he's still a 10-year-old boy who gets hurt when his friends get mad at him.

The Passion of Reverend Ruckus

• So many of the main characters are pushed into awkward and hopeless situations, what with Granddad trying to stop Ruckus's racist religion with Tom getting lulled into it, and Huey trying as hard as he can to save an innocent man from getting executed. The situation is so large that it makes Huey cry and pray until a sudden miracle saves everyone.

Season 2

Attack of the Killer Kung-Fu Wolf Bitch

• Luna's flashback. She grew up with an abusive father which caused her to run away from home, only to date a series of abusive boyfriends. All of this trauma is why she distrusts men so much.
  • Luna forgives Robert and leaves, only to get another call of bad advice from her friend, which finally pushes her into blowing herself up with a hand grenade.

Home Alone

• Huey and Riley's relationship hits rock bottom in this episode. It's actually heart-rending to see how low the brothers' respect for each other gets, in particular Huey treating Riley like a prisoner (complete with orange jumpsuit and solitary confinement) and blaming him for Granddad leaving.

The Story of Gangstalicious Part 2

• After being outed as gay in a tell-all book by his ex, Gangstalicious is rejected by the Hip-hop community, his fans are shocked at the news and Lethal Injection crew cancel their plans to collaborate with him. He then calls his manager, says that no one will want to work with him now, and believes that his career is over.
• Riley coming to terms with the possibility of being gay after spending most of his life being fiercely homophobic can hit very close to home to people who actually spent most of their lives in the closet, especially those who were similarly homophobic as a defense mechanism. The fact that Riley is a child is also very tragic as many children, particularly African-American children, grow up not knowing how to handle their sexual orientation and might even be taught that they are wrong, much like Riley. The cherry on top is Robert's comforting of his grandson, even after he spent a good portion of the episode trying to cure his gay.

The Uncle Ruckus Reality Show

• Uncle Ruckus is unable to handle the truth that was right under his nose the whole time: a DNA test revealed that he is of pure black ancestry, not a white man with "re-vitiligo" as he had always believed.
  • After trying and failing to live the way he thinks a black person is supposed to, he becomes so depressed that he tries (but fails) to commit suicide by hanging.

Season 3

Bitches to Rags

• Seeing the entirety of Thugnificent's mansion in a decrepit state compared to what it was in "The Story of Thugnificent" and "Shinin'"; it's a depressing indicator of how bad things have gotten for Thugnificent.
• Thugnificent's look of dejection when Riley laughs at his dance after the former complained about Sergant Gudda's dance; he probably thought that even Riley stopped liking him and almost came to the realization that maybe his Rapping career really was over. If not for Riley indirectly catching onto the fact that his insecurities was beginning to get to him and still reassuring his support of him, he would have given up then and there.
• Everyone in the Lethal Interjection crew abandoned Thugnificent (justified in Flonominal's case since he already accepted that the crew was finished), except Leonard...and he still gets mistreated by Thugnificent despite being the only one who stuck around with him.
• Given that Sergant Gudda looked up to Thugnificent prior to being trashed on the radio, imagine the feeling of betrayal he felt when his idol of all people was berating him.
• This entire exchange between Robert Freeman and Thugnificent
  Robert: Boy what on Earth are you doing?! You trying to get yourself killed?
  Thugnificent: (looking defeated) I don't know what to do...
  Robert: Well get a job!
  Thugnificent: I tried that...
  Robert: (Sincerely) Well try again!
  Thugnificent: (dejected) You don't understand, pops; I always wanted to do this rap thing...and then, yknow by some miracle, I actually pulled it off! I just thought...I just thought it would last longer...
• The entire premise of the episode; Thugnificent's rapping career is essentially on its last legs and he's practically doing everything he can to keep it going but just keeps making things for himself and everyone else worse when he tries to keep it afloat...his fanbase and people in general grew tired of his music and old-school rappers like him, his record label abandoned him, he lost Flonominal as a friend, and after a failed music deal with Steve thanks to Ed Wuncler III's greed? He's lying on the sidewalk unconscious, and essentially comes to terms that everything he ever worked for has gone down the drain.

A Date with the Booty Warrior

• The ending, during which the prisoner confesses to Huey his guilt for the crimes that landed him in prison, and wishes things could have been different. He knows he's ruined his life, and all he can do is rape other inmates for the rest of his life.

The Color Ruckus

• Uncle Ruckus reveals that he was raised by a cruel and abusive father, Mister Ruckus. Mister had an extremely short temper and would beat around his own little son for little or no reason. Eventually Mister threw Uncle out of the house, much to the protests of Mister's wife and younger sons. Uncle was so traumatized by the ordeal (pictured above) that it's the reason why he hates his own race so much.
  • Mister Ruckus himself experienced similar misery at the hands of his own abusive mother Nelly, and was also similarly mistreated by the white men who employed him (he lived during the height of Jim Crow). Whenever Mister wasn't drunk and angry, he would just sit down and cry instead.

It's Goin' Down

• The life of Jack Flowers. Every woman he ever loved, they were all brutally murdered by terrorists and criminals. As a secret agent who specializes in counter-terrorism, he has seen and done awful deeds that have also emotionally scarred him.

Season 4

Good Times

• The entirety of this episode 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 to 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.

Granddad Dates a Kardashian

• After the frankly hilarious reason for Kardashia's hospitalization (her butt exploded, mortally wounding her), there's 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...

Freedomland

• Expanding on the terrible events from "Good Times", Ed Wuncler II and Uncle Ruckus force the Freeman family and countless other people onto a plantation-themed amusement park, to drive home the point that they are (quite literally) slaves to Wuncler. The Freemans are forced to endure all kinds of abuse and humiliation. But fortunately, they put a stop to this by rioting and burning down the park.