Lifetime of Simpsons

Favorite Episodes: Season 19-24


Hi there everyone, and welcome back to another day of rattling off my favorite episodes of the Simpsons. And, pleasantly, we have a pretty solid batch of episodes to talk about today. These seasons were kind of a mixed-bag, but for the most part each season had a very great episode somewhere inside to highlight for this wrap-up. So, without further ado, let’s get to the episodes!




Season 19 – “Eternal Moonshine of the Simpson Mind”

Season 19

We’re starting things off today with a serious head-trip, folks. This episode is another example of the show playing around with the format, trying something different in order to avoid being stale. And it worked out really well. This is an episode that send Homer on a memory-less voyage across Springfield, desperately trying to figure out the missing pieces of his memory while getting increasingly horrified that he’s done something that will forever change his marriage. It’s a fun little scavenger-hunt that features some incredibly solid voice-acting from Dan Castellanetta, who doesn’t always get the credit he deserves for his performances as Homer. It’s a really fun episode, and we get to see Homer try all sorts of weird things to solve his conundrum, even using some sort of memory-viewing device from Professor Frink, which kind of strains the logic of the episode, but doesn’t keep it from being one of the more innovative episodes from this era.

“Eternal Moonshine of the Simpson Mind” was written by J Stewart Burns and directed by Chuck Sheetz, 2007.




Season 20 – “Homer and Lisa Exchange Cross Words”

Season 20.jpg

I’ll be real with you folks, Season 20 isn’t exactly the strongest assembly of episodes. There’s plenty of fine episodes, but very few really stand out to me. However, if there’s one thing that I’m a huge mark for, it’s episodes that revolve around Homer and Lisa’s relationship, and this episode takes that in a very interesting direction. For most of the episode Homer and Lisa are on very different stories, doing their own thing. Homer gets a lot of money as a professional break-up surrogate, and Lisa is becoming a famous cross-word solver. But, everything comes together when Homer starts betting his money on Lisa, and ends up better against her at one point. This shatters their relationship for a while, and Homer realizes he needs to do anything he can to mend the relationship that seems like it could be permanently destroyed. But, like you’re expect, things end up working in the end, and their relationship gets fixed. What I really find so interesting about this episode is the fact that the episode is very well-put together. It starts as two plots, and dovetails together to form a third combined plot in a way that really worked well, and felt very realistic.

“Homer and Lisa Exchange Cross Words” was written by Tim Long and directed by Nancy Kruse, 2008.




Season 21 – “The Squirt and the Whale”

Season 21

Hey, speaking of Lisa, let’s talk about an episode that legitimately made me cry! Lisa’s intense passion and love for all living things in the world is one of the things that I most love about her, and this episode puts that on full display. When Lisa discovers a beached whale, she makes it her goal in life to spend time with the animal, trying her best to give it some sort of comfort while the people of Springfield vainly try to figure out how to save it. But, they fail. The whale dies, and Lisa is forced to experience her first true brush with death, and the realization that sometimes there’s nothing that you can do to fix things, and its out of your hands. This episode takes Lisa’s grief, and let’s us examine it, not destroying the emotion by tossing in some jokes to cut the mood, and I really appreciate it for that.

“The Squirt and the Whale” was written by Matt Warburton and directed by Mark Kirkland, 2010.




Season 22 – “The Great Simpsina”

Season 22

Oh look, another Lisa episode! And an incredibly solid one at that. I was kind of blown away by this episode when I first saw it, primarily because it checked an incredible amount of my personal boxes. We had a Lisa episode where she learned how to do practical magic from a curmudgeonly old stage magician all in order to defeat the rise of a Criss Angelesque goth magician. That’s a hell of a story right there. Lisa’s friendship with this old magician becomes really fun, especially when we start to see how sad his life is, and the idea that Lisa becomes something of a surrogate daughter to him. It’s just a hell of an episode, folks. It has heart, charm, and plenty of laughs, which is kind of everything I want from an episode of the Simpsons.

“The Great Simpsina” was written by Matt Warburton and directed by Chris Clements, 2011.




Season 23 – “The Book Job”

Season 23

This isn’t going to be all about emotional episodes though, because sometimes all you need is an utterly ridiculous and incredibly entertaining story. And this is what we get today. “The Book Job” is an episode that almost feels too weird to explain. It’s about Homer and Bart realizing that there’s a lot of money in the young-adult literature business, so they put together an all-star group of cohorts in order to write a successful book. And for some reason its all set up like it’s a heist, specifically one of the Soderberg Oceans movies. There’s nothing too deep about this episode, it’s just an incredibly good time.

“The Book Job” was written by Dan Vebber and directed by Bob Anderson, 2011.




Season 24 – “Gone Abie Gone”

Season 24

The last episode that we’ll be talking about today is one of the rarest types from this period of the show. A great Grandpa-centric episode. It’s all about the family trying to find Abe after he seems to vanish, while falling down a rabbit hole and learning about Abe’s life post-Mona. The time period doesn’t really make a whole lot of sense, but learning that Abe had a second wife who he made beautiful music with while embracing a more artistic part of his life is a whole lot of fun. The canon doesn’t always add up, but who cares? It’s a really fun episode that shines a great light on Abe, and the idea that no matter what, he loves Homer, and will do whatever he needs to do in order to take care of his son. It’s just a really fun episode.

“Gone Abie Gone” was written by Joel H Cohen and directed by Matthew Nastuk, 2012.



And there we go! Another list of favorite episodes. We only have one more day of these lists, before next week’s round-up of rankings. So, meet me back here tomorrow to close out this list of favorite episodes!




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