I know I’m showing my age when I talk to people and say something like, “Remember when The Simpsons was really funny?” and they don’t. Awkward. Anyway, among my favorite Simpsons moments from their best seasons (3-9) are the musical numbers. Here are my top picks, but the list is by no means exhaustive. Leave your favorites in the comments.
The only thing more brilliant than parodying Terry Cashman's "Talkin' Baseball" with lines like “Ken Griffey's grotesquely swollen jaw/Steve Sax and his run-in with the law" is getting Cashman himself to perform it. Despite the ear-buggy tune’s age (the episode “Homer at Bat” aired in 1992), it’s still one of the better known Simpsons songs, even among casual fans.
The Canyonero Song
The “country-fried truck endorsed by a clown” is a perfect satire of not only truck commercials, but also razor blade ads, the Marlboro Man, and any other marketing that targets the male mind’s fixation on masculinity and excess.
"Everyone Hates Ned Flanders"
Homer’s musical career may have peaked with “Baby on Board,” but lyrical brilliance never struck the Be Sharps quite like it does here with the comparison of Flanders to both Frankenstein and Dr. No.
Hank Scorpio’s Theme
“You Only Move Twice” is, in my humble opinion, the best Simpsons episode ever. It focuses on Homer’s brief employ with dream boss/super villain Hank Scorpio, and the Bond-theme-esque tune at the end is pitch perfect. Hey guys, what's your least favorite country, Italy or France?
“We Do” (the Stonecutters’ Song)
Conspiracy theorists fear that secret societies control national governments or are hiding knowledge of extraterrestrials. The Stonecutters do all that, but they also have much more innocent aims. In this drinking song, they brag about suppressing the metric system in the U.S. and maintaining Steve Guttenberg’s career, among other things.
The Monorail Song
The song has some great lines (Is there a chance the track could bend?/Not on your life, my Hindu friend!), but its real strength is in laying bare Springfield’s mob mentality and lack of foresight and reason, and holding up a mirror to the shortcomings of our own political processes.
“See My Vest”
This one tips its hat to two different Disney films, parodying “Be Our Guest” from Beauty and the Beast and exposing Mr. Burns’ inner Cruella de Vil.
“We Put the Spring in Springfield”
This tribute to “that little extra spice that makes existence extra nice” won a Primetime Emmy for Outstanding Music and Lyrics.