Original air date: October 19, 1997After Lisa's saxophone gets crushed in the street, Homer tells the story of how Lisa first discovered her musical talent — which coincides with the tragic tale of how Bart's first day of kindergarten turned him into the troublemaker he is today.This is the third of four episodes produced by Al Jean and Mike Reiss instead of the current showrunner (in this case, Bill Oakley and Josh Weinstein). Jean would return as showrunner starting in season 13.
- All Asians Look Alike: In the Krusty TV movie, "Krusty" is shown telling his Chinese stepson Chan-Ho he's breaking up with his mother Mia Farrow, but the boy actually tells him Chan-Ho is elsewhere, and he himself is Chin-Ho.
- As Himself: Fyvush Finkel as himself playing Krusty the Clown in the TV movie The Krusty the Clown Story: Booze, Drugs, Guns, Lies, Blackmail, and Laughter!
- The Bus Came Back: Dr. J. Loren Pryor, the Springfield Elementary School psychiatrist from the early seasons comes back during flashbacks discussing Bart's and Lisa's potential.
- Lunch Lady Doris, who was retired from the show after voice actor Doris Grau passed away, appears in the flashbacks.note She'd permanently be back starting in season 18, voiced by Tress MacNeille.
- Celebrity Paradox: The Tracey Ullman Show was once America's leading source of musical comedy and "crudely-drawn filler material."
- Comic-Book Time: This is the first episode to play with the established timeline of the Simpson family. Bart is entering kindergarten in 1990, when previously that was the year Maggie was born and Bart would have already been 10 in 1990 (if he were born in 1980, he would have been kindergarten-aged in 1985, which was when Homer and his friends became a barbershop quartet). The writers have always been upfront about this since the characters never age; Al Jean even admitted that they knew they'd get into this the moment they first mentioned Homer and Marge's senior year.
- Comically Missing the Point: Homer's tale about how Lisa got her saxophone initially ends with Bart's miserable first day of school.Homer: And that my children, is the story of Bart's first day of school.
Bart: Very nice.
Lisa: Yeah. Except you were supposed to be telling the story of how I got my saxophone!
Homer: (beat) D'oh!
- Cycle of Revenge: Seeing Lisa upset about her destroyed saxophone, Homer offers to break something of Bart's. When Bart protests, Homer says he'll break something of Maggie's to make it up to him.
- Fiction Isn't Fair: Principal Skinner introduces some members of staff to the new students, including school bully Jimbo.
- Jimbo: (making a punching gesture) I look forward to whaling on all of you.
- Heck, the entire episode uses this trope to justify why Bart hates school. He actually looked forward to it, until everyone and everything on his first day served to Break the Cutie in ludicrous ways — like the kindergarten teacher declaring him "not college material" simply because he threw in an extra clap while singing "Bingo".
- Freudian Slip: Principal Skinner accidentally introduces himself as "Principal Sinner". As the kindergartners laugh, Skinner mutters "That's it, I've lost them forever..."
- Hilariously Abusive Childhood: Lampshaded.Homer: (to young Bart) Now, son, on your first day of school, I'd like to pass along the words of advice my father gave me.
(thought bubble with Abe and young Homer)
Younger Abe: Homer, you're dumb as a mule and twice as ugly! And if a strange man offers you a ride, I say take it!
Homer: (muttering) Lousy traumatic childhood!
- Hyperaffixation: When Homer and Lisa visit a music store:Homer: So, what do you like, Lisa? Vio-ma-lin? Tuba-ma-ba? Oboe-mo-boe?
Lisa: That one!
Homer: Oh, saxo-ma-phone.
- Hypocritical Humor: This scene between Homer and young Bart.Homer: Bart, son? You want to play catch?
Young Bart: No.
Homer: When a boy doesn't want to play catch with his old man, something is seriously wrong!
Abe: (wearing old-time baseball uniform) I'll play catch with you, son!
Homer: Get the hell out!
Abe: I'm gone.
- After watching the Krusty TV-Movie mentioned above, Homer calls him a bad father, as Maggie walks by carrying an electric drill.
- I Take Offense to That Last One!: When young Bart first made fun of Principal Skinner:Young Bart: (singing) Skinner is a nut, he has a rubber butt!
Skinner: Young man, I can assure you my posterior is nothing more than flesh, bone, and that metal plate I got in 'Nam.
- Lampshade Hanging:Homer: Our family was suffering through its worst crisis ever: Bart was miserable at school and Lisa's gifts were going to waste.
Bart: Uh, Homer, it's five years later, and I'm still miserable at school.
Lisa: And my gifts are still going to waste.
- Really Dead Montage: Towards the end, as Lisa plays her new saxophone, we see a montage of Lisa playing her original saxophone set to Gerry Rafferty's "Baker Street".
- Sadist Teacher: Bart's kindergarten teacher.Teacher: And the ugly duckling was amazed to realize it had grown into a beautiful swan. So you see children, there is hope for anyone.
Bart: Even me?
- Shout-Out: Homer and Marge sing their own version of "Those Were the Days", spoofing the opening sequence of All in the Family, complete with narrator saying "The Simpsons is filmed in front of a live studio audience" and Homer calling Bart "Meathead" afterwards.
- Homer finds Twin Peaks to be brilliant, even though he has no idea what's going on.
- Start of Darkness: The flashback of how Lisa got her saxophone also contains the tragi-comic story of how Bart became a bad kid at school (his kindergarten teacher openly told him he had no real future and he was bullied by Jimbo Jones).
- Stepford Smiler: Marge reveals that sometimes she feels so smothered by being a mother that she wants to scream until her head explodes. Sadly, no one shows any concern for her about it and she continues repressing her feelings.
- Stylistic Suck: Marge's loud, high-pitched, out of tune delivery of the line "and you knew where you were then" cemented the All in the Family parody.
- Take That!: To The WB network.Michigan J. Frog: (singing) We're proud to present on the WB, another bad show that no one will see! (disgustedly walking off) Ah, I need a drink...
- Two Roads Before You: After witnessing his antics, Skinner tells Bart he can either continue being a class clown or apologize right now and be well-behaved.Skinner: Now, what do you say?
Bart: Eat my shorts.