Mr. Burns puts on a variety show at the Springfield Bowl in exchange for rebuilding the town after it's burned to the ground. However, when the event brings back bad memories for the old man who bombed when he first performed there 100 years ago, Burns tries to muster up the courage to perform again in an effort to redeem himself.

Homer finds a new friend in a woman who acts just like him, while Mr. Burns' search for a clan to play his virtual-reality family leads him to hire Marge, Bart, Lisa and Maggie, since Burns intends to play the father.

Homer takes the family on a "hate-cation" to Boston when he catches Bart rooting for a rival football team. But after discovering the appeal of candlepin bowling over his regular bowling, and finding a better safety inspector job at a candy factory, they agree to move there. Meanwhile, Lisa discovers how much Boston has to offer academically compared to Springfield.

In the 27th annual Simpsons Halloween special, Mr. Burns makes the children fight to the death for a day in his personal reservoir, Lisa's imaginary friend kills her real friends, and Bart is recruited to Moe's group of secret barfly agents.

Bart and Lisa investigate Krusty's new "Krustaceans" candy, while Homer asks Marge to help him dress for a promotion at the nuclear plant and Kent Brockman deals with the changing media world.

Homer coaches the kids' lacrosse team with Milhouse's dad Kirk, who really needs a friend. Kirk then disappears upon hearing Homer rant about him being a loser, just as the team needs him for the championship game.