Here’s the fifth installment.  I should also mention, which I haven’t yet, that this list does not contain any Treehouse of Horrors episodes.  To me, those are a different entity all together.

#20: A Star is Burns

Original Air Date: March 5, 1995

PLOT: The town holds a film festival and invites Critic Jay Sherman to sit on the board of judges.

Normally, a crossover episode seems really desperate for a series to attempt. But here, it works brilliantly; probably not unrelated to the fact that the Simpsons lost many a writer and showrunner to ‘The Critic’, so each show was bred from similar DNA. Also, Jon Lovitz was already a regular guest star, so Jay Sherman was sort of like writing yet another guest appearance for him. This episode runs like a well-oiled machine, despite its novelty.

Its fun to see the different takes on filmmaking from the many townspeople in Springfield. From Moe’s musical to Hans Moleman’s ‘Man Getting Hit By Football’, each character’s unique personality comes through in their submissions.

I am also a big fan of any appearance by Jon Lovitz on the show. Between he, Kelsey Grammar, and Phil Hartman, its hard to choose which one performs best when given a part on the show. And I love the competition that grows out of Homer’s jealousy. Because its petty; just like we all know Homer to be. It culminates into an impromptu rendition of the Oscar Mayer jingle by Jay, which is the only way this silly rivalry can reach an apex.

Let us all not forget that the most important part of this episode is that it gave us ‘Boo-urns’

#19: Homer’s Barbershop Quartet

Original Air Date: September 30, 1993

PLOT: Homer tells the story of his short-lived time as a barbershop quartet band member.

As a fan of the Beatles, I truly love this episode. It’s a huge testament to the show to be able to get one of the Beatles, let alone all save for the late John Lennon. Here, George Harrison is the Beatle they got and they did not waste his presence. There are plenty of Beatles references in this episode from the name of the Be-Sharps to the album covers all the way to the end credits (“I’d like to thank you on behalf of the group and I hope we passed the audition”).

The main storyline is great, as its a completely fresh past for Homer. I love the interaction within the group of the four characters and also Chief Wiggum. I lost count of how many times I’ve said “This bird’s gotta fly!”. To add an exclamation point to that line, the Simpsons pay fan service by having Chief Wiggum crash through a window. That always gets me.

But the interstitial storyline I love too. I like the swap meet scene especially, because we get to see different sides to the Springfield citizens. Like Moe trying to sell Oyster Shell Lucille Ball. Pure genius.

#18: Bart vs. Australia

Original Air Date: February 19, 1995

PLOT: Bart pretends to be a government official over the phone, landing him in hot water with the continent of Australia

For better or worse, this is the episode that seemingly started the tradition of “The Simpsons Go Abroad” episodes. Since then, we’ve seen the family go to Japan, Brazil, England, Canada, Africa, and just about any place else imaginable. This is the best by far because while the other episodes politely lampoon their host locations, the Australians don’t fair any better than the people of New Orleans did in “A Streetcar Named Marge”. The Simpsons have a great time skewering this (in the Simpsons’ warped mind’s eye) backwards culture and its hilarious to watch.

Bart is at his usual bad self and that’s what this episode is primarily about. Bart gets called on his crap and has to deal with the consequences. The rest of the family is subjected to background filler. As the name of the episode suggests, its a Bart-heavy episode. But it has some great Homer moments, including him pissing off an American guard.

#17: The City of New York vs. Homer Simpson

Original Air Date: September 21, 1997

PLOT: The Simpsons travel to New York so that Homer may retrieve his car, which Barney illegally parked at the World Trade Center.

This episode, through no fault of its own, is somewhat dated, based solely on the inclusion of the Twin Towers in the plot. I can see how this episode could make someone uncomfortable watching (especially one, now awkward joke), but this is a hilarious episode.

Its all about Homer’s pure hatred for New York, based on a terrible experience he once had. This gives way to a fantastic old-fashioned flashback to the theme from “The Sting”. The flashback is capped with one of my favorite lines in the series and one I use to cap off my own long-winded stories: “…And that’s when the CHUDs got me.” Its such a throwaway line that I didn’t fully understand it until I got older. And now its just purely brilliant.

New York fares better in this episode then, say, Australia, Brazil, or New Orleans in their respective episodes, but this is hardly a glowing love letter to the city. The people are rude, the garbage flies in your face, and the Jets buy ad space on the subway to find a quarterback. You know, just like the real New York. As a person that was born there and now currently works there, it’s fun to see the city get put under the Simpson microscope, which is probably the main reason this episode barely edges out the similarly-themed Bart vs. Australia.

#16: Bart on the Road

Original Air Date: March 31, 1996

PLOT: Bart gets a fake driver’s license and takes a road trip to Knoxville, Tennessee with Milhouse, Nelson, and Martin. Meanwhile, Homer and Lisa bond after he takes her to work for the day.

I’m a huge fan of the road film sub-genre so this episode is right up my alley. This episode is wildly unique as it does have the episodic structure of a road film, albeit condensed to a 22-minute show.

I love the group chemistry among the boys. You usually get to see Bart interact with one of them, but with three, you get the interactions between all four of them and it makes for some interesting pairings. I always love whenever Nelson shares a scene with Martin, as they are such a perfect odd couple. I also love Milhouse… just in general. Here we get plenty of him as well as a trip to the Cracker Factory, which is one of my favorite recurring jokes in the show’s history.

The B-story is a very nice Homer and Lisa story. It’s rare that we get a story between the two that doesn’t involve them butting heads. In this one, its a sweet connection that they share as father and daughter and really creates a nice little heart to the otherwise Bart-centric show.