Nice to see this thread. I’ve mulled over this concept time-to-time.

Initially, I’d have left Season 9 alone. As mixed as it is, I still feel the good outweighs the meh/bad. But then I realized there simply aren’t enough decent episodes in Season 10+ to put together a quality 26-episode season; there’s enough for maybe a 13-episode season? I dunno — I quit watching the show regularly after Season 14.

SEASON Ω

“Lisa’s Sax”
“Treehouse of Horror Ω” (includes the intro from “XII”, The HΩmega Man from “VIII”, The Terror of Tiny Toon from “IX”, & I Know What You Diddily-Iddily-Did from “X”.)
“The Cartridge Family”
“The Two Mrs. Nahasapeemapetilons”
“Lisa the Skeptic” (I’d re-edit this one to remove/reduce Lisa’s antagonism towards belief in angels)
“Realty Bites”
“Miracle on Evergreen Terrace”
“Bart Carny”
“The Joy of Sect”
“Dumbbell Indemnity” (I’d re-edit this one to keep Moe & Renee together.)
“Lisa the Simpson”
“King of the Hill”
“Lost Our Lisa”
“Natural Born Kissers”
“The Wizard of Evergreen Terrace”
“Bart the Mother”
“D’oh-in’ in the Wind”
“Lisa Gets an “A””
“Maximum Homerdrive”
“Take My Wife, Sleaze”
“Alone Again, Natura-Diddily”
“Days of Wine and D’oh’ses”
“The Computer Wore Menace Shoes”
“Trilogy of Error”
“The Blunder Years”
“Behind the Laughter”

I’d also incorporate Stupid Sexy Flanders from “Little Big Mom” and the Adam West Batman scene from “Large Marge” in any of these episodes. Dunno where they’d fit best.