Double, Double, Boy in Trouble

Joe Montana as himself

"Double, Double Boy in Trouble" is the third episode of The Simpsons' twentieth season. It first aired on the Fox network in the United States on October 19, 2008. Bart meets a rich boy name Simon Woosterfield, who happens to be Bart's exact look-alike. Because of this, the two decide to switch homes; Simon enjoys his time with the Simpsons while Bart discovers his rich new half-brother and sister are out to kill Simon, so they can inherit the vast Woosterfield family fortune. Former NFL football player Joe Montana guest stars as himself. In its original airing, the episode garnered 8.09 million viewers.

The episode begins with Maggie, Homer and Bart at the Kwik-E Mart. Apu tries to get Homer to buy the last lottery ticket by claiming that the last ticket is always lucky. When Homer is about to take money out to buy the ticket, Bart attempts to jump off a shelf and land in Chief Wiggum's cart full of marshmallows. However, Wiggum moves the cart and Homer has to race over to catch his son, while Lenny walks up to the counter and buys that last ticket. Lenny wins $50,000, which makes Homer jealous. Apu decides to put it in his book, Tales of the Kwik-E Mart. At Moe's Tavern, Lenny announces he is going to spend his winnings on a giant party at the Woosterfield Hotel for all of his friends. The Simpson family cannot find Bart when it is time to leave, because he is upstairs in the attic with a water gun full of cat urine. When he is about to shoot it at Rod and Todd Flanders in a wagon below, Marge steps in and Bart accidentally sprays her with the urine, so Marge has to wear a mediocre "back up dress" to the party. Homer and Marge wonder why Bart cannot behave and decide he went bad in utero when pregnant Marge accidentally swallowed a small drop of champagne after Mayor Quimby christened a new Navy vessel, the U.S.S. Float-and-Shoot. The drop landed on a gestating Bart and turned him bad. At Lenny's party, Bart discovers that Lenny will give out vacuuming robots in gift bags. Bart activates all the dangerous settings on them and they attack the party guests. When everyone finds out that Bart is responsible, Marge takes away Bart's non-dice board game privileges, after Bart says she already took away his TV and video game privileges. In the bathroom, Bart meets Simon Woosterfield, a kid who is both Bart's exact look-alike and part of a billionaire family whose wealth even eclipses Mr. Burns'. They also meet an adult Bart double who has a wife that, to Bart's disgust, looks like a female version of Milhouse.