After Smithers is crushed by Mr. Burns' lack of affection towards him, other characters attempt to find a boyfriend for him. Meanwhile, Milhouse competes against Jack de Forest, a boy who acts exactly like Humphrey Bogart, for the lead role in a school production of Casablanca, so he can act alongside his own unrequited love, Lisa.
Tropes:
- Abhorrent Admirer: One more point for Milhouse: he convinces all of the Springfield Elementary bullies to attack Jack so he will be removed from the running to play Rick.
- Arrested for Heroism: Jack fends off all of the school bullies single-handedly, but he is the one who gets in trouble with Skinner for fighting and taken out of the Casablanca production.
- Bait-and-Switch:
- When Smithers and his new boyfriend are discussing travel plans, the scene cuts to a map and a dotted line goes from America to Cuba, suggesting they're already going there. It turns out they're still in Springfield and Smithers' boyfriend is just showing a planned route.
- When Smithers and his boyfriend get a license, it turns out to be a fishing license.
- At the school play, Milhouse seems to give a good performance as Rick Blaine, but turns out to be Jack disguised as him.
- Celebrity Paradox: George Takei appears As Himself, having previously played the characters of Akira and Wink.
- Contrived Coincidence: When he actually goes to Cuba, Smithers sees a carnival mask that resembles Burns, plus a mural of the man being driven out of Cuba in 1959.
- Everybody Knew Already: Of a sort. Homer, Lenny and Carl already knew that Smithers is gay before the events of this episode.
- Hidden Depths: Subverted. We are led to believe for a moment that Milhouse could be a good actor if he is motivated to do so, but it turns out that Lisa secretly got rid of Milhouse and helped Jack supplant him with a Latex Perfection mask.
- Identical Stranger: Homer encounters a gay man who looks exactly like him, whom he promptly hires to impersonate him while visiting his father Abe.
- Latex Perfection: Jack uses a Milhouse mask to perform as Rick Blaine in Casablanca, and only Lisa knows the difference (because she is the one who helped him get it).
- Lorre Lookalike: When Ralph quotes Ugarte's line "You despise me, don't you?" from Casablanca, his eyes go wide like Peter Lorre.
- The Peter Principle: Enforced by Skinner to give Milhouse the role of Rick after taking Jack out of the race for not letting the school bullies beat him up: as he tells Lisa, it is "constructive" for idiots to be placed in roles that they are absolutely bad at doing and letting the train wreck do the rest.
- Shout-Out: At the end of the episode, Moe is convinced by "that funny Bogey kid" to search for gold in Mexico, being joined by Willie.
- What Happened to the Mouse?: We never find out what Lisa did to get rid of Milhouse in order for Jack to supplant him, and where he is during the play.
