Seymour and Superintendent Chalmers embark on an 800-mile trip to Cincinnati, Ohio for a speech.
This episode provides examples of:
- 555: Mr. Largo's guitar lesson ad give the phone number 555-0105.
- All Bikers are Hells Angels: Parodied. Skinner and Chalmers enter a biker bar, but instead of bikers, the bar is full of cyclists, who nevertheless act like Badass Bikers. One cyclist crushes an oxygen can with his forehead, and two others play Five-Finger Fillet with a wrench.
- Alternate Catchphrase Inflection: At least two from Chalmers: he lets out a shocked "Ski-nner!" emphasizing the first syllable in a Dude, Not Funny! moment, and he later calls helplessly "Skinner?" when it seems that Seymour's left him to be attacked by the cyclist gang.
- Ascended Meme: Skinner and Chalmers pass a restaurant called "Steamed Hams", the nickname for the "Skinner And The Superintendent" segment from "22 Short Films About Springfield".
- Book Ends: The main plot starts with Sherri and Terri, along with Lisa and Janey, skipping rope with a song making fun of Skinner. The episode ends the same way, but with a song praising him instead.
- Borrowed Catchphrase: Of a sort. After overhearing Chalmers' promise to fire him, Skinner yells, "CHALMERS!" in the same way the latter typically yells his name.
- Brick Joke:
- Early in their trip, Skinner and Chalmers pick up a Shakespearian improve troupe, which annoy Chalmers to the point of nearly killing them. In The Stinger, Marge surprises the family with tickets to the same troupe.
- The episode begins with Skinner failing at giving Chalmers a high five and then practicing on a skeleton in the detention room. When it ends, Skinner is back in the detention room and describes his joy to Bart by giving the skeleton a perfect high five.
- A Day in the Limelight: An episode solely devoted to Skinner and Chalmers, with the Simpsons only having one or two lines in the entire episode, to where even Homer (who mind you is the ONLY character in the entire series yet to miss a single episode) only appears in the stinger and with a single line, making this the closest he's gotten to actually missing an episode. To his credit, Bart is the one who gives a mini Rousing Speech to Skinner and tells him that You Are Better Than You Think You Are.
- Dude, Where's My Respect?: Skinner is treated like dirt by everyone since the episode's start, to the point where word of his failures at the start of the episode quickly spreads among the students. Sherri and Terri skip rope with a song about it.
- Ear Worm: In Agnes's car, Skinner and Chalmers are stuck listening to "Timothy" by The Buoys on repeat since the cassette is stuck in the player and the volume knob is broken. Later as they drive out of Missouri in the judge's car, Chalmers triumphantly belts out the chorus.
- Earn Your Happy Ending: Skinner finally gets his due after nearly fifteen seasons of being the series' Butt-Monkey.
- Epic Fail: Skinner's attempt to high-five Chalmers results in him accidentally slapping his crotch. He later practices on a skeleton, but gets his hand tangled in its pelvis.
- Foreshadowing: Skinner's suit is noticeably darker than usual in this episode, almost matching that Chalmers'. It makes it less noticeable when the two accidentally wear each other's jackets after their big fight.
- Giant Food: At one point Skinner and Chalmers crash into a silo of genetically modified soy beans, which are about the size of soft balls.
- Gratuitous Iambic Pentameter: The hitchhikers from the Shakespearean improv troupe always speak like this when they're in character. After hearing them do a bit, an impressed Skinner adds, "Pentameter checks out!"
- Handicapped Badass: Because of his knowledge of local veteran's events, Skinner is able to summon a whole crew of wheelchair-bound para-athletes to defeat the cyclist gang, knowing that they're having a marathon nearby.
- Improv Comedy Is Inane: Principal Skinner is driving Superintendent Chalmers to a convention when he picks up a Shakespeare-theme improv troupe. Their act drives Chalmers crazy, causing an accident that totals the car. In The Stinger, the Simpsons end up going to a performance of the troupe, and everyone except Marge hates it.
- Irony: Skinner has Bart, his eternal frenemy, to thank for his chance to take the initiative and get on Chalmers's good graces.
- Jerkass Ball: Chalmers and Skinner hold it alternatively in this episode, showing them both at some of their worst.
- Laser-Guided Karma: Goes both ways for Skinner and Chalmers:
- Chalmers' trip goes wrong in nearly every way possible after decades of being a Jerkass to Skinner.
- Skinner is the one responsible for ruining the plane trip in the first place. Chalmers doesn't take it well.
- Motorcycle Dominoes: Parodied when in the cyclist bar, Skinner accidentally topples the cyclists' GPS trackers while they were charging.
- Noodle Incident: When Chalmers talks about "that one principal" that superintendents have to deal with, the camera cuts to four pairs of principals and superintendents. One is wearing prison uniforms and are handcuffed to each other, another is covered in seaweed, another has a boa wrapped around them, and the last pair is covered in arrows.
- Out of Focus: With Skinner and Chalmers in the forefront, the Simpsons themselves make only token appearances. Bart is the only family member with plot relevance, goading Skinner to stand up to Chalmers. Lisa also appears in the two double-dutch gags that bookend the episode. Homer, Marge and Maggie only appear in The Stinger, where the whole family goes to see the Shakespeare improv troupe. It's even telling that this is the first episode in over 32 seasons where Homer only has a single line and it's during The Stinger, making it the closest he's ever gotten to missing an episode, an act he is the only member of the main four NEVER to have done.
- The Precious, Precious Car: Skinner manages to convince his mother to borrow her Buick. Not long afterwards, it gets totaled by an accident involving a Shakespearian improv troupe and a silo of genetically engineered beans. It doesn't look too bad... until it goes up in flames.
- "The Reason You Suck" Speech: A lot of dirty laundry and lingering resentment between Skinner and Chalmers gets unloaded in the episode:
- Chalmers really, really dislikes Skinner, and was going to replace him with the magnet school principal because he has no tolerance for neediness and dependence. He simply didn’t do it because he didn’t want to hurt Skinner's feelings.
- Skinner feels very slighted by Chalmers’s ingratitude after years of trying to please him. It’s especially hurtful when you realize Skinner knows he’s stuck in a worthless school with some of the most cynical, inept teachers ever conceived by the American educational system, and will never be thanked. He’ll only get demands and more demands and Chalmers doesn’t see that.
- The Reveal: Two. Chalmers was going to fire Skinner in exchange for someone else, and Skinner poisoned this other person to make it look like food poisoning.
- Road Trip Plot: Skinner and Chalmers drive to Cincinnati to attend a school principal convention, where Chalmers is giving the keynote address.
- Satchel Switcheroo: After their fight at the bed and breakfast, Skinner and Chalmers inadvertently put on each other's coats, so Skinner ends up with Chalmers' keynote speech, while Chalmers has to go on stage with just Skinner's conversation starter cards.
- The Scream: Chalmers goes ballistic when Skinner’s slip of the tongue gives him away.
- Shout-Out:
- According to Matt Selman, Principal Finch is named after Chris Finch, David Brent's rival on The Office.
- The theme from WKRP in Cincinnati is heard twice: when Chalmers arrives in the city hitching a ride on a spaghetti truck, and at the episode's end when he and Skinner enjoy three-way at Skyline Chili. The episode's credits also reference WKRP's, even using the same iconic music.
- Similar Squad: The audience at Chalmers' keynote turns out to be full of superintendents whose trip there was complicated by an errant principal.
- Tampering with Food and Drink: Chalmers' original partner for the trip dropped out after eating poké the previous night and waking up sick, but during the brawl at the bed and breakfast, Skinner lets it slip that he put black mold on his dish.
- Tears of Joy: Skinner sheds a few when he hears Chalmers' You Are Better Than You Think You Are speech about him. Chalmers notices and sheds a few of his own.
- The Television Talks Back: During Chalmers' freakout, the airplane is showing Game Night. Its star, Jason Bateman, appears to tell Chalmers that the passengers are taking off their shoes.
- Took a Level in Badass: Skinner’s military training is finally demonstrated twice: when he calls on disabled veterans competing in a Paralympic event nearby, and later when he goes on a Roaring Rampage of Revenge against Chalmers. The principal can actually fight.
- Top-Heavy Guy: Inverted with the cyclist biker gang and then played straight with their opposite numbers the Wheel Team Six Para-Marathoners, who are in wheelchairs but maintain their upper body strength ("You're never alone when you're a veteran of the US Armed Forces. And I do mean armed.")Cyclist: Their biceps are bigger than my quads!
- What the Hell, Hero?: Skinner goes on a violent rampage against Chalmers because the latter would fire him in exchange for another principal. Chalmers regrets it later after Skinner still returns to him with his keynotes.
- Where the Hell Is Springfield?: According to a sign Skinner and Chalmers pass on the way, it is at least 800 miles from Cincinnati. They also have to pass through Missouri to get there.
