Original air date: October 19, 1997
After 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.
- 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!
- Author Avatar: Al Jean modeled the boy who eats worms on himself, as he ate worms as a child. He even looks like Jean.
- Batman Parody: Bart sings a song called Buttman.
- Because You Were Nice to Me: The episode shows the route of Bart and Milhouse's friendship surprisingly started with Bart feeling this way towards Milhouse, before Bart became a troublemaker when he was just a depressed kid who Milhouse was willing to sit with and gave him the confidence to joke around in front of the class.
- Blatant Lies: Homer flashes back to having said to Barney as a kid "Let's Never Drink Again!" Then in the present day he says, holding a beer, "And we never did!" as he proceeds to take a sip.
- Bread, Eggs, Milk, Squick: Bart makes fun of Principal Skinner, singing "Skinner is a nut, he has a rubber butt!". Skinner responds by saying, "Young man, I can assure you my posterior is nothing more than flesh, bone, and that metal plate I got in 'Nam.".
- 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. To add an extra level of confusion, while produced two seasons earlier, the episode didn't air until 1997. As a consequence, the reference to the characters being five years younger in 1990 didn't make sense even when the episode first aired.
- 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!
- Crush Parade: Lisa's prized saxophone accidentally sailed out her bedroom window and into the street where it's run over by a car, a truck, stamped on by Nelson (who then points at it and mocks, "Ha ha"), and concludes with Hans Moleman on a tricycle who falls over to the side when his front tire hits what remains of the flattened saxophone. (And to top it all off, the sax produces a "Wah Wah" sound after all that.)
- 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 his kindergarten teacher declaring him "not college material" simply because he threw in an extra clap while singing "Bingo".
- Freudian Excuse: This episode goes out of the way to explain that Bart is troublemaker today because his kindergarten teacher basically said he'd never amount to anything just because he wasn't as quick as the other kids to catch on to things.
- Freudian Slip: Principal Skinner accidentally introduces himself as "Principal Sinner". As the kindergartners laugh, Skinner mutters "That's it, I've lost them forever..."
- Hate Sink: Bart's kindergarten teacher is nothing but a sadistic, mean spirited bully.
- 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.
- This scene between Homer and young Bart.
- I Need a Freaking Drink: From the Michigan J. Frog parody:"We're proud to present on the WB, another bad show that no-one will see-ee-eee! Ugh, I need a drink."
- 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.
- Jerkass: Bart's kindergarten teacher and Skinner.
- Karma Houdini: Bart's kindergarten teacher. The episode shows that the cruel treatment he received from his teacher contributed greatly to shaping Bart's future behavior. Simply put, she wrote down Bart as a lost cause because he didn't catch on to things as quickly as the other kids, and has been emotionally and psychologically abusing him ever since. He was just five years old and he was already considering suicide. Its likely that by now this teacher is still putting down children that she deems slow, unwittingly turning them into Future Barts.
- Kill It with Fire: Marge shows Homer a picture an upset Bart drew:Marge: Homer, I want you to look at this drawing Bart did.Homer: [watching TV] Oh, it's beautiful! Oh, oh, let's put Bart's beautiful drawing up on the fridge!Marge: Homer, stop. Will you please look at the drawing?Homer: Oh, all right. What...[looks at drawing]...aaah!! Burn it! Send it to hell!
- 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.
- Literal Metaphor: When Homer sees Lisa looking at the music shop, he says "A musical instrument? Could that be a way to encourage a gifted child? (looking upward) Just give me a sign!". That's when the shop owner puts a sign in the window saying "Musical instruments: the way to encourage a gifted child.", to which Homer says "Eh, works for me." and they go inside and purchase Lisa's saxophone.
- Name One:Homer: Marge, name one successful person in life who ever lived without air conditioning.Marge: Balzac!Homer: No need for potty mouth just because you can't think of one.
- Nightmare Fuel Coloring Book: Bart did a "Sad" drawing◊ after his first day at school.Marge: Homer, I want you to look at this drawing Bart did.Homer: (takes drawing but without taking his eyes off of the TV) Ohhh, it's beautiful! Oh! Oh let's put Bart's beautiful drawing up on the fridge—Marge: Homer, stop! Would you please look at the drawing?Homer: Oh, alright. (looks) What a— (screams) BURN IT! SEND IT TO HELL!Marge: I think we're going to have to get Bart some help.Homer: Get it away!
- Noodle Incident: Grandpa blurts out at one point "I realized I could make money selling my medication to deadheads." He chooses not to elaborate further.
- Not Helping Your Case: After Lisa points out there's a cockroach in with the pickled eggs in front of the health inspector (see Oh, Crap! below), Moe tries to smooth things over by giving the guy a margarita...that has a syringe in the glass. Moe weakly claims it's a parasol when the inspector glowers at him.
- Oh, Crap!: After Lisa notices the pickled egg jar contains a cockroach.Moe: Thats nice. Who are you then, sweetheart? The health inspector?Man at bar: No, but I am.
- Overly Literal Transcription: As Homer dictates a dedication for Lisa's saxophone, he tells the clerk to write "To Lisa, never forget your Daddy loves-", when he drops the sax on his feet and says "D'oh!", which is transcribed as "To Lisa, never forget your Daddy loves D'OH!" In the end of the episode, Lisa gets a new sax with the dedication "To Lisa, may your new saxophone bring you years of D'OH!".
- Parental Favoritism: When Dr. Pryor tells Homer and Marge that Lisa is gifted, Homer suggests that he and Marge brush Bart's problems aside, claiming that his life is over (despite him only being five) and that Lisa's the wave of the future.
- Playing Catch With The Old Man: Bart rejects Homer's offer to play catch. Homer says that there's something wrong when a boy doesn't want to play catch with his father; Abe (wearing an old-fashioned baseball uniform) then offers to play catch with Homer, but Homer tells him to go away.
- Racial Face Blindness: 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.
- 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 finds Twin Peaks to be brilliant, even though he has no idea what's going on.
- Song Parody: 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.
- Small Role, Big Impact: The Preschool Teacher's treatment of Bart, is the reason Bart is Bart today. What makes it worse is that Bart was just 5 years old and her actions made Bart actually consider suicide. To specify, the teacher basically wrote off Bart as a lost cause because he didn't catch on to things as quickly as the other kids:Bart: (singing) B-I-*clap*-*clap*-*clap*-O and Bingo was his name-o.Teacher: (writing on a clip board) Extra clap; not college material.
- 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 future whatsoever 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...
- The Thing That Would Not Leave: Apu, who lampshades this with "For no reason, here's Apu..." as he joins in the reprise of "Those Were The Days", and periodically makes wisecracks.Homer: Aww, but Marge, am I doomed to spend the rest of my life sweating like a pig?Bart: Yeah, not to mention looking like a pig, eating like a pig...Apu: (through window) Don't forget the smell!Homer: Will you get off my front lawn?Apu: Why don't you make me?Abe: (covering his eyes) Where's Maggie? Where's Maggie? I'm not kidding, I can't see! My retinas have detached again!(Homer and Marge laugh)Apu: (walking in, laughing) He is blind as a bat!
- 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.