- Pretty much the entire "Wings of a Dope" episode, in which Buckley's angel comes back, particularly the scene in which he and Luanne bounce on the trampoline after first meeting. Fireflies appear around them and fittingly enough, Dream Academy's "Life in a Northern Town" plays in the background. The last scene is even more powerful - Buckley bounces on Luanne's trampoline high enough to disappear from her sight, after which she believes he is gone for good and goes back into the house. He returns to Earth, exclaims, "Cool, a new record!" and then, as the song begins to play again, is shown walking off toward the horizon, pulling a halo from his pocket and donning it as the credits begin to roll. The scene where Luanne is by the trampoline crying listening to "Angel Flying Too Close to the Ground" as she waits for Buckley and hopes he isn't "gurardianin' some other girl," followed by Peggy's motivational speech, is a close second.
- "Wings of a Dope" aired several weeks after the 1999 Columbine High School Massacre. Mike Judge received a fan letter from one of the survivors of the tragedy who secretly had a crush on a fellow student at her school and said if she made it out alive, she would ask the person out. That person ended up actually being one of the shooters and it broke the survivors heart that she didn't get the chance to confess her love and she couldn't outwardly grieve for him due to his actions. The survivor credited Peggy's speech at the end of the episode in helping her release her grief and apparently quoted Luanne's "guardianin' some other girl" line in her letter.
- Bobby breaking down into tears and going through a Heroic BSoD after Marie breaks up with him in "And They Call It Bobby Love."
- "Chasing Bobby" can be pretty depressing if you're a truck or any general car owner. Hank's truck is on its last few miles and Hank is utterly devastated because of how much the truck means to him; this is one of the few episodes where we see him break down in tears. Hank's refusal to get a new truck and his attempts to save it lead to him taking his frustration out on his family, when it's clear he doesn't mean to.
- Almost any episode from the first few seasons which focuses on Luanne. Whether it's the reveal of her mother's alcohol problem, general discussion of her dysfunctional family, her futile struggles with beauty school, her boyfriend's death and return as an angel, or her facing sexual harassment at work, the early Luanne episodes tended to be pretty heavy.Luanne: Mama, please...
Leanne: Would you QUIT calling me that?
- "Propane Boom", the second season finale. When the Mega-Lo-Mart explodes as a result of a negligent propane leak, Peggy screams in terror for Hank and Luanne, who are both inside. The scene is not Played for Laughs, with the season ending upon Boomhauer calling 911 and a horrified Peggy watching him do so, unaware if her husband or niece are alive. The following episode, "Death Of A Propane Salesman", has Luanne dealing with the loss of her hair and bottling her emotions by pulling a Sinead O'Connor act, but she soon breaks down alone in her room after reading the last birthday card Buckley gave to her.
- Peggy lamenting about how all of her birthdays always end in disaster in "Strangeness on a Train".
- Peggy crying when she finds out that her big feet were being used to satisfy internet perverts in "Transnational Amusements Presents: Peggy's Magic Sex Feet."
- Bobby telling Peggy that she shouldn't feel bad about her big feet just because the perverted podiatrist said so and the fact that Bobby accepts the fact that he's fat (or "husky" as his jeans says) and there are people out there who pick on him for it, but he doesn't let it get him down because he has friends, a girlfriend (at least until he and Connie broke up), and most people see past the fact that he's "the fat kid" and see that he's a very funny, friendly person.
- Cotton was a complete and utter, unrepentant Jerkass towards Hank his entire life, but when suffering from internal wounds, severe burns, and a shellfish allergy at the same time, Hank doesn't even think much of it because his dad's "been through much worse", even outright denying there'd be long-term problems because of how stubborn a bastard Cotton can be. When he finally starts thinking it could worse than he thought, not only does Cotton promptly chew out Hank and fake his death to screw with him, the two minutes he leaves the room and Peggy with Cotton to cool off is all Cotton needed to basically commit suicide by stopping his heart - just to spite Peggy. The sad part isn't so much Cotton's death, as it is Hank just not being able to come to terms with it all properly or emotionally due to how much emotional abuse Cotton heaped on him his whole life.
- In "The Man Who Shot Skretteberg," Hank and the others recover from their first paintball match, acting like shellshocked veterans. Though played for laughs, their interactions are very similar to how actual war veterans can turn out. If seen without context, new viewers could easily mistake this scene for a completely serious portrayal of people with PTSD.
- Boomhauer's Break the Haughty moment in "Dang Ol' Love" and his subsequent 10-Minute Retirement.
- The ending of "Won't You Pimai Neighbor" where Bobby chooses what's in the mirror- Connie's reflection- meaning he doesn't want the celibate life of a monk if it means he can't be with her. And it turns out the mirror was the object belonging to the Lama, but the monks decided that the choice was still legitimate. Connie's reaction, is to shed a single tear of happiness.
- Bobby and Connie's breakup.
- Quite a few Ladybird-centric episodes have their moments, but "To Kill a Ladybird" takes the cake. Ladybird is feared to have rabies and Hank, while grappling with the fact that he may have to put her down shuts the garage down and turns on some loud power tools which fail to mask Hank audibly sobbing.
- "Manger Baby Einstein" has the Gurgle-Gurgle subplot. The rest of the Manger Babies save for the octopus are destroyed by Dale as revenge for Luanne plagiarizing a story he wrote. While they were just inanimate puppets, they have been a running joke since Season 2 and seeing their destruction feels like a recurring character is being killed off.
- "Pretty, Pretty Dresses". Bill is already a horribly depressed character, but watching him break as thoroughly as he does here is really awful. Fortunately, it leads to a Heartwarming Moment by the end.
- The Cold Opening gives you a pretty good idea of what you're in for. Watching Bill break down crying seemingly out of nowhere juxtaposed to the jolly "Sleigh Ride" instrumental can either be surprisingly funny or outright unnerving to watch.
- When Peggy is about to break to Dale about how Nancy has been cheating on him all these years with John Redcorn, when Joseph (John Redcorn's biological son) comes out of the house and asks Dale for some money to see a movie. Dale gives him extra for snacks, and you realize how much Dale loves Joseph (even though Joseph is biologically not his). Peggy can see this too and decides not to tell the truth.
- In the first episode, Hank is under investigation by Social Services, because people mistakenly thought he hit Bobby. When the investigation is called off due to the social worker's incompetence, Bobby (who intercepted the call) lies and tells Hank that if he continues to lose his temper, the government will take him away. When Peggy learns from the case manager that the investigation was halted a week earlier, she confronts Bobby...and he admits that he is doing it because he doesn't believe Hank loves him.
- When Bobby accidentally burns down the church, Cotton takes the blame for it. His reasoning is that Bobby's life would be tainted forever by this (even though Bobby burning the church was an accident brought on by him trying to cover up the fact that he got sick on lutefisk). If it was Cotton's fault, however, it could be written off as Cotton being mentally unstable and sexist (since a lot of people thought the church burning was a hate crime over a female pastor being hired). As huge of a jerkass as Cotton is, this is one of the few times he shows that he does have a heart underneath all his bluster and cruelty.
- The Season 4 premiere, where Peggy is recovering in a full bodycast after falling out of her plane. At first she's elated from the thrill of surviving, but as she spends more time completely helpless, her depression takes over. It reaches its peak when Cotton's new baby GH has to stay at their house so Bobby can take care of him, and we get a long scene of Peggy being treated just as much like a baby by Hank as GH is by Bobby, to the point where she is fed through a bottle. You can see her rapidly realizing how utterly immobile and helpless she is, and how degrading the whole experience is for her even before the tears start flowing. What makes her explode with anger was when she remembered why she jumped from the plane: Didi having Cotton's baby. She couldn't stand the idea of Cotton having another baby to torment (because of how he abused Hank) while Didi is too much of an airhead to raise a child, all while she herself desperately wanted more children but was never able to conceive them due to Hank's narrow urethra. And here she is, stuck in a body cast, helplessly watching Cotton and Didi neglecting "Their beautiful new baby that they don't even want." The only good tear jerker? Peggy finally makes the baby stop crying by rocking him to sleep with the only part of her body not in the cast: her toes.
- The episode "Vision Quest" makes a big-time woobie out of John Redcorn. He desperately wants to be a part of his illegitimate son's life, but doesn't want Dale to find out that Joseph is his biological son. Dale has been pushing Joseph to hang out with a crowd of delinquents in order to be seen as "cool", something that Redcorn cannot allow. He arranges the titular vision quest as a way of straightening Joseph out and attends the trip despite agreeing to stay away. The saddest part is when Joseph is yelling for his "dad" (Dale, who had gone off into the woods with Hank and Bobby) with Redcorn watching from behind a tree a few feet away. The look on Redcorn's face shows just how much Joseph really means to him and he knows how bad of a role model Dale is despite the love he has for Joseph.Redcorn (to Nancy): Dale's going to ruin Joseph's life! I have relied on others to raise my son for too long. No offense, but it ends now.
- "As Old as the Hills": Peggy's reaction to what's supposed to be a light-hearted anniversary slide show. At first Hank thinks she's crying about a slide that shows Hank and Peggy as old people, but she clarifies that the photos of her and Hank as a young, newly-married couple were what upset her, because she didn't recognize them. This is one of those bits of dialogue that only gets more relevant as you age.
- The series finale where Hank and Bobby finally find something they love to do together (grill beef) and have a small barbecue for the neighbors is both this and heartwarming. After 13 years, Bobby has finally found a hobby he can bond with his father over.
- "Blood And Sauce" revealed much to Bill's sorrow that the majority of his family has died off. His Aunt Esme and cousin Violeta died of fever and Passed in Their Sleep respectively. Gilbert goes on to explain the majority of the Dauterive line died barren, were impostors or committed to mental institutions, leaving only he and Bill as the last of their family.
- A more Meta example. The death of the real Tom Landry in February 2000 makes his speech to Hank in his varnish-induced dream "in Hillennium" that much more poignant and tragic. He assures Hank that no matter what the future holds not to live in fear. As the episode was about the Millennium Bug paranoia it's sad to know Tom didn't get to experience the 21st century himself.
- In-Universe Hank was once tricked by his cousin Dusty (of ZZ Top) that Landry had died. He believed he was being pranked a second time when Dusty tried to tell him how Tom Landry died for real. Hank is legitimately mortified he went to work on that day.
- In "Full Metal Dust Jacket", Peggy goes through hell just to be allowed to join a ladies' book club, and when she finally gets in, the women lie about the book club being canceled while calling Peggy a windbag when (they think) she's out of earshot. Peggy tries to give a dignified goodbye, but once she gets to the parking lot she breaks down crying. Even if Peggy can be full of hot air, this is one of the moments you can feel bad for her.
Tear Jerker / King of the Hill