The Simpsons has been on TV for over three decades, evolving over the years with the rest of the culture in terms of what's socially acceptable. While some elements have aged better than others, there are some that have taken unexpectedly complicated turns, including one major character, whose increased depth across the course of the series also came with some very rough elements.

While he may be an interesting and occasionally pitiable character, the problematic elements of Moe Syzlack make him a difficult character to root for with a modern sensibility -- making him perfect for a modern reexamination.

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Moe is actually one of the earliest characters introduced in The Simpsons, first appearing in the series premiere "Simpsons Roasting on an Open Fire." The cantankerous owner of Moe's Tavern -- a frequent hangout spot for Homer and his friends -- Moe is often portrayed as something of a sweet-hearted scumbag. Although he's casually disgusting and always on edge, he does have a soft side to him that usually comes out when with his few friends, including Homer. Moe has also developed connections with the rest of the Simpsons family, including Bart, who constantly pranks him with crank phone calls. Moe seems unaware that Bart is responsible for them, however, with episodes like Season 3's "Burns Verkaufen der Kraftwerk" revealing that Moe thinks Bart is adorable.

However, Moe has a far more problematic relationship with Marge, the matriarch of the Simpsons family. Multiple episodes have played up Moe's attraction to Marge, which has ranged from flirtation to aggressively manipulating events so the pair can be together. He has confessed romantic feelings for her in episodes like Season 16's "Mommie Beerfest," despite his friendship with Homer. Marge has always been polite but forceful in her refusal to even consider the idea, but Moe never lets up. Whenever she refuses him, Moe retreats inward -- often insulting her under his breath and even spying on her. This more sinister side of the character extends to many other women in Springfield, with Moe even hinting in some episodes that he's legally a registered sex offender.

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That element of the character makes him horrifying from certain perspectives, and a difficult character to actually like. What makes this more complicated is his established depression, and how the show explores some heavy topics with him. Moe's lack of social life, standing, wealth and companionship weigh on him, and multiple episodes have featured Moe attempting to end it all -- only to fail due to some unexpected occurrence or intervention of a friend, such as Homer. When the show isn't poking the situation for dark comedy, it can actually be used for strong dramatic effect -- with some of Moe's most open and compelling character beats coming from his attempts to overcome his depression and move past his suicidal urges.

Unlike the incredibly problematic Glen Quagmire from Family Guy -- who is shown being much more aggressive and successful with women -- The Simpsons often face the genuine pitiful sadness of Moe's life head-on and doesn't shy away from just how sad of a man someone like Moe would be. But the more aggressively sleazy elements of the character make it harder to root for Moe to find new personal heights. It becomes especially difficult in episodes where Moe ends up alone with Marge's children, watching over the kids of a woman he's repeatedly sexually harassed. The show has even made Moe charming in later years, almost excusing his antics and making him a viable temptation for Marge.

Perhaps there's a way for the show to confront this darker side of Moe while exploring how he became that way, and how he could learn to actually improve himself instead of just trying with Marge again the next chance he gets. It would be a difficult task, but it's one that could push Moe into a more modern sensibility.

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