27 Years Ago Today, King of the Hill Delivered a Christmas Episode That Was Also One of Bill’s Best Ever

27 years ago today, King of the Hill released a Christmas episode that also happened to be one of Bill Dauterive’s best episodes in the series ever. King of the Hill has had a few Christmas specials over the course of its original run years ago, and many of them used the holiday to highlight the awkwardness of the familial gatherings itself. It was a particularly rough time for Bill as while he was always portrayed as the sad sack of the neighborhood, it was clear that the holiday season fully turned that into a depression that his friends needed to monitor to keep him from hurting himself.

It’s a dark undercurrent with many of Bill’s stories, and the best Bill episodes had used that to fully address his issues. 27 years ago today, on December 15, 1998, King of the Hill debuted “Pretty, Pretty Dresses” that directly called attention to the fact that Bill had been left by his ex-wife years before. It was an episode that saw him go through a full mental breakdown, and it’s with Hank’s help that he’s able to get back to his old self. All while also being set during the Christmas holiday season.

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Premiering during the third season, King of the Hill’s “Pretty, Pretty Dresses” has a title that already alludes to Bill’s terrible upbringing. There’s a previous episode where Bill makes an offhand comment about how his father used to punish and ridicule them by making him wear dresses, and he sort of whispers “Pretty, pretty dresses” as a way to infer that he took some delight in this. But then the episode uses that as a springboard to explore more of Bill’s past in full as well.

Because while it had been previously revealed that Bill’s ex-wife had run out on him, it wasn’t until this episode in particular that fans found out she was named Lenore. It turns out that Christmas is actually the anniversary of when Lenore first left him, and it’s why he has such a brutal spiral every year since. It’s an episode that tests Hank’s friendship with Bill as it confirms that he feels a sense of obligation after Bill helped block him during football plays when they were in high school (which is a very important time in Hank’s life), but also reveals that Bill has become a real issue during the holidays for all of his friends.

It’s also where Bill starts to lose himself even more. He adopts a pet iguana that he names after his ex-wife, reveals that he still gets her presents in the hopes that she returns one day, and often attempts to take his own life because of how depressed he gets at this time of year. It’s become so rampant that it’s not only something the entire neighborhood has become aware of, but has become a notable burden on all of them. Pretty much souring their own holiday.

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The episode then takes a much darker turn as Bill hits what he realizes himself is “rock bottom.” He begins to wear Lenore’s dresses, and even speaks in a higher tone of voice pretending that he’s a returned Lenore. He keeps up this charade for a while, and even shows up to the Hill’s Christmas party in a full dress. It almost takes a darker turn as those around him get aggressive for doing so, but Hank has to pretend he’s Lenore to snap Bill out of it.

This wa the darkest Christmas episode that King of the Hill ever released, but it was much needed for Bill himself. This truly was the lowest that Bill had ever sunk in the series before, and notably has not dropped to that level ever since. Because while Bill continued to be sad during the holidays (and even extended his pathetic grasp on it to unhealthy levels in future seasons like with “‘Twas the Nut Before Christmas”), it was never on this grounded, fully suicidal level again. This was as distressing as it ever had been.

The Christmas tone of the episode is buried underneath that darkness, sure, but it’s also why King of the Hill is so great at what it does. It took a realistic look at the holiday with a character who reflects the darker emotions that the holiday might elicit. It bravely hits all of this head on, and while it might not be first King of the Hill Christmas episode you choose to revisit, it’s certainly one of the most important specials the series has ever released.

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