5 Most Genuinely Heartbreaking King of the Hill Episodes of All Time, Ranked

King of the Hill is seeing quite the resurgence in recent days. Thanks to co-creators Mike Judge and Greg Daniels bringing the Hills back years following their original series finale, the animated show hit the ground running when it landed on Hulu last year. Confirmed for multiple new seasons, Arlen enthusiasts are counting down the days until they once again see Hank Hill in the driver’s seat. In looking at the past of this one-time Fox series, we decided to gather five of the most heartbreaking episodes of the series that prides itself on humor, proving that the Hills can get emotional when they want.

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5.) “Pretty, Pretty Dresses” – Season 3, Episode 9

King of the Hill’s Bill Dauterive has long been the punching bag of the series, which can often mask the loneliness of the character and how depressing Bill’s life can become. Even the revival series started with Bill being a shut-in within his own house following Hank and his family’s departure from the United States. In “Pretty, Pretty Dresses,” the animated series sees Bill during the holiday season, completely losing his grip on reality due to his ever-depressing circumstances.

During this season three episode, Bill reveals that the holidays aren’t just a tough time for him, thanks to being alone, this is also the time when his ex-wife, Lenore, decided to break up with him. The episode sees Bill attempting to take his own life, naming a new lizard after his former partner, and arriving at the Hills’ holiday party wearing a dress. While the installment eventually sees Hank going so far as to wear a dress himself to help his friend, snapping Bill out of his funk, it goes to show just how dark the show could be when it came to its characters, presenting a heartwrenching series of events.

4.) “Wings of the Dope” – Season 3, Episode 23

King of the Hill’s third season began with the after-effects of the “Mega Lo Mart” exploding to cap off season two. While Hank and Luanne escaped with their lives, not every animated character was so lucky. Buckley, Luanne’s aloof boyfriend, was killed in the blast, and it was a major plot point that Luanne had to deal with throughout season three. Everything comes to a head in the episode, “Wings of the Dope,” which has lasting implications for Hank and Peggy’s niece.

Wings of the Dope didn’t just see Buckley return as an angel in Luanne’s mind; it also studied the idea of changing one’s life in the face of trauma and bullying. As she struggles with the loss of Buckley, Luanne eventually finds herself saying goodbye to him as she decides to attend community college and forego her original decision of graduating from beauty school. For a show that typically injects humor into more mundane scenarios, an episode focusing on loss and struggling to forge a new path in life made for quite the departure.

3.) “Dang Ol’ Love” – Season 6, Episode 20

While Bill might be the punching bag of King of the Hill, Boomhauer certainly had his fair share of comic relief moments in the series. During the sixth season episode, “Dang Ol’ Love,” the blond-haired supporting character does something that many viewers didn’t see coming: he falls in love. Throughout the animated show, Boomhauer is routinely shown as a ladies’ man, picking up dates like playing cards, but in this installment, he finds himself on the other foot.

In the installment, Boomhauer falls head over heels for the neighborhood’s ice cream lady, Marlene, despite Bill having feelings of his own for her. Eventually, Marlene dumps Boomhauer, sending the latter into a spiral as he finds himself receiving words of wisdom from none other than Dauterive. Seeing Boomhauer so heartbroken was a wild change of pace for the character, and somehow, this fact makes the moment hit all the harder.

2.) “To Kill a Ladybird” – Season 4, Episode 9

Ladybird has long done something that many others never have in King of the Hill, the canine gained Hank’s affection. In fact, it often seems like Hank loves his dog more than other members of his family. It’s why the episode, “To Kill a Ladybird,” hit so hard in that, following the pooch’s encounter with a raccoon, Hank has to struggle with the idea of killing his best friend. In one solemn moment, Hank sits alone in his garage, thinking about what he might be required to do should Ladybird have rabies.

The fate of Ladybird, surprisingly enough, remains a mystery to this day. In the revival series on Hulu, Hank’s dog is nowhere to be found, though, considering how old Ladybird was in the original series, it would make sense that the animated canine passed away between the thirteenth and fourteenth seasons of the series. Should we eventually see the death of Ladybird in a flashback, we have to imagine that it will make for one sad episode.

1.) “Leanne’s Saga” – Season 2, Episode 19

While Luanne might be best known for one of her biggest struggles revolving around the loss of Buckley, her relationship with her mother, Leanne, made for another emotional beat in King of the Hill. Throughout the first season, Luanne’s parents had mostly been mentioned in passing, never making an appearance in the first season. The reasoning behind why Leanne was absent from the show was stabbing her ex with a fork.

“Leanne’s Saga” sees both Luanne and Bill at their lowest, with Bill falling for Leanne and abused as a result by her. Eventually, nearly coming to blows with Peggy, Leanne decides to leave the Hill home in the episode and effectively leave as Luanne’s mother once again. Luanne and Bill would eventually find their own versions of peace but Leanne certainly never played a role in their journeys moving forward.

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