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

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Recently, King of the Hill has become popular again. After the show ended its original run, co-creators Mike Judge and Greg Daniels brought it back, and it quickly found a new audience when it started streaming on Hulu last year. With multiple new seasons already confirmed, fans are eagerly anticipating Hank Hill’s return. We’ve looked back at the show’s history and picked out five of the most emotionally impactful episodes, proving that even a funny series like King of the Hill can be surprisingly moving.

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

Bill Dauterive from King of the Hill is often the target of jokes, which can hide how lonely and sad his life actually is. The recent revival series begins with Bill isolating himself at home after Hank and his family move away. In the episode “Pretty, Pretty Dresses,” Bill’s difficult circumstances cause him to struggle with reality during the holidays.

In this episode, Bill shares that the holidays are difficult for him not only because he’s alone, but also because his ex-wife, Lenore, ended their relationship around this time. The episode depicts Bill at a very low point, including a suicide attempt and finding unusual ways to cope, like naming a lizard after Lenore and showing up to a party in a dress. Hank eventually tries to help Bill by dressing up in a dress himself, successfully pulling his friend out of his depression. This episode demonstrates the show’s willingness to explore very dark and emotionally challenging storylines for its characters.

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

The third season of King of the Hill started by showing the fallout from the explosion at Mega Lo Mart, which ended the previous season. Although Hank and Luanne survived, not everyone did – Luanne’s boyfriend, Buckley, was killed. This became a significant storyline for Luanne throughout the season, culminating in the episode “Wings of the Dope,” which had a lasting impact on her life and her relationship with Hank and Peggy.

The ‘Wings of the Dope’ episode wasn’t just about Luanne imagining Buckley as an angel; it also explored how people cope with difficult experiences like trauma and bullying. While grieving Buckley’s death, Luanne ultimately decides to change her plans – she chooses to go to community college instead of finishing beauty school. This was a surprisingly serious episode for a show known for finding humor in everyday situations, as it dealt with loss and the challenge of starting over.

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

Although Bill Dauterive often takes the brunt of the jokes in King of the Hill, Boomhauer has plenty of funny moments too. In the episode “Dang Ol’ Love” from season six, he surprises many viewers by falling in love. Throughout the series, Boomhauer is usually portrayed as someone who easily attracts women, but in this episode, the tables turn and he finds himself as the one falling for someone else.

This episode centers around Boomhauer developing a strong crush on the local ice cream vendor, Marlene, even though Bill is also interested in her. Marlene ultimately rejects Boomhauer, leaving him devastated and surprisingly receiving advice from Dauterive. It’s unexpected to see Boomhauer so heartbroken, and that makes the scene particularly impactful.

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

I’ve always loved how King of the Hill handled Ladybird. It’s amazing—she genuinely won Hank’s heart, and honestly, sometimes it feels like he loves that dog more than anyone else! That’s why the episode “To Kill a Ladybird” was so gut-wrenching. Seeing Hank grapple with the possibility of having to put down his best friend after that raccoon fight was just brutal. There’s this one scene, him alone in the garage, just quietly thinking about what he might have to do if Ladybird had rabies… it really gets to me every time.

It’s surprisingly never been explained what happened to Ladybird, Hank’s dog from the original series. She doesn’t appear in the Hulu revival, and given her age, it’s likely she passed away sometime between seasons thirteen and fourteen. If the show ever shows Ladybird’s death in a flashback, it would probably be a very emotional moment.

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

Luanne’s storyline on King of the Hill often focused on difficult times, particularly after the loss of her dog, Buckley. Another significant emotional element was her relationship with her mother, Leanne. For much of the first season, Luanne’s parents were only talked about, and never actually shown on screen. The reason for Leanne’s absence was revealed to be that she had stabbed her former partner with a fork.

In “Leanne’s Saga,” both Luanne and Bill struggle with difficult times. Bill develops feelings for Leanne, which leads to her mistreating him. The situation escalates to a near-fight with Peggy, and Leanne ultimately leaves the Hill household, abandoning her role as Luanne’s mother for a second time. While Luanne and Bill eventually find some happiness, Leanne doesn’t participate in their healing process.

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2026-01-08 00:45