This . . . this was insanely hard to do. My first list probably consisted of 40+ episodes. I finally trimmed that down to 24. Getting 10 from that? Ridiculous. Ordering those 10? Ohhhh, fuck you.
10. Coming to Homerica (Season 20)
- People seem to moan these days that The Simpsons stopped being a great series after the 90's. While I think the show peaked around then, there's still a ton of great episodes that have come around since, and I think most people just aren't paying attention. One such great episode is this one here - a hilarious satire of the current immigration debate in America - and it's just from last season.
9. Homer at the Bat (Season 3)
- This is the earliest episode on my list, and it seems to mark the beginning of when the series truly hit its stride. "No hustle either, Skip!"
8. Trilogy of Error (Season 12)
- I don't see this episode referenced very much, but I feel it represents one of the most fun breaks in form the series has done (the story structure was modeled after the films Go and Run, Lola, Run.) Plus, it's just plain funny. "You could be one of them TV magic queers!"
7. 22 Short Films About Springfield (Season 7)
- This one's getting a ton of mentions, and deservedly so. The run of dialogue between Skinner and Chalmers is just astoundingly funny.
6. Cape Feare (Season 5)
- This is the very best of the Sideshow Bob episodes, and that's saying a lot. "He remaaaaaaaaains and Eng-LISH-maaaaaaan!"
5. Homer vs. The Eighteenth Amendment (Season 8)
- One of John Swartzwelder's finest, and that puts it above at least FIFTY other great episodes, as Swartwelder is the series' most prolific (and perhaps funniest) writer. Plus, Dave Thomas in a great turn as Rex Banner. "Uhhh . . . the best damn pet shop in town!"
4. Homer's Enemy (Season 8)
- This episode probably best exemplifies the series' ability to poke fun at itself and even make you question the most basic premises. "Frank Grimes - or Grimey, as he liked to be called . . . ."
3. You Only Move Twice (Season 8)
- Swartzwelder wrote it. Albert Brooks (perhaps the best guest star the series has ever had) is in it as one of the most iconic secondary characters ever. The writers tried to shake-up the basic premise of the show. And it's damn funny. I won't quote the whole thing, but the run of hammock jokes may be the funniest bit of improvised dialogue ever.
2. Mother Simpson (Season 7)
- The Simpsons is at its best when it has you emotionally invested, yet laughing out loud. This is arguably the episode that evokes the most intense emotional reaction while keeping you laughing all the way (Maggie Makes Three, Lisa's Substitute, and my number one choice would be the other major contenders for this throne, in my view.) Plus, it has Glenn Close in a great guest-starring role. Plus plus, the series that is perhaps best known for a new joke every few seconds spends its final moments just reflecting quietly on what has happened.
1. HOMR (Season 12)
- I'm sure basically everyone will disagree with me putting this at number one, but it's my personal favorite. Why? First off, the Homer/Lisa stories almost always get to me emotionally. This one is more focused on Homer himself, but his relationship with Lisa is brought sharply into focus here. In addition, twelve seasons on, the show is still playing with its basic premise and asks "Why is Homer so dumb?" On that note, the show takes the opportunity to examine what it's like to be intelligent in a society of the ignorant. Plus, it's just ridiculously funny. "Notice I no longer say 'libary' or 'tomorry." On top of all of that, Homer's "I'm taking the coward's way out" note to Lisa kills me every time. It's touching to see him communicate his admiration for Lisa, yet heartbreaking to see the finality in his decision.
Honorable Mentions (Because I just can't not mention them, and in no particular order):
The Color Yellow (Season 20) (Another great one from just last season.)
Missionary: Impossible (Season 11) "SAVE ME JEEBUS!"
Homie the Clown (Season 6) " . . . and all the other piddlin' crap that I wouldn't touch with a ten foot clown-pole."
Lemon of Troy (Season 6) (Seeing Shelbyville equivalents of Springfieldians is surreal.)
El Viaje Misterioso de Nuestro Jomer (Season 8) (A touching Homer and Marge story, a literally surreal story, and JOHNNY CASH AS SPACE COYOTE.)
Simpsons Roasting On An Open Fire (Season 1) (The first episode to air really set a great tone for the whole series.)
Lisa's Substitute (Season 2) (It seems cliche now, but "You are Lisa Simpson" is just brilliant.)
And Maggie Makes Three (Season 6) ("Do it for her." *cue tears*)
Homer the Heretic (Season 4) ("We interrupt this public affairs program to bring you a football game.")
The Itchy & Scratchy & Poochie Show (Season 8) ("Poochie died on the way back to his home planet.")
The Cartridge Family (Season 9) (Another Swartzwelder classic, rife with satire.)
Simpsons Bible Stories (Season 10) (A sequel to David & Goliath as done by Jerry Bruckheimer. "I thought you were dead!" "Nope.")
The Simpsons Spin-Off Showcase (Season 8) ("Damn straight, Troy, my man.")
Homer The Great (Season 6) (Stonecutters. 'Nuff said.)
I Love Lisa (4) ("We are the mediocre presidents!")
By the way, can you tell I love Season 8? I never truly noticed myself until I made this list.
And Sousa, if you're soliciting write-ups, I'd like to give it a shot.