When Lenny wins the lottery and invites the Simpson family to a celebratory party at a posh hotel, Bart meets his doppelganger, Simon Woosterfield, who happens to be a member of the richest family in Springfield. Simon and Bart decide to switch places, and Bart arrives at the lavish Woosterfield mansion only to find football great Joe Montana (guest-voicing as himself) hanging around the estate. As Simon adjusts to the simple life over at the Simpson household, Bart begins to notice his wealthy new siblings acting strangely toward him. With some frightening words of wisdom from Mr. Burns, Bart realizes his new siblings are plotting his demise so they can inherit the Woosterfield family fortune all for themselves. Lisa and Simon must reach Bart before he goes from riches to ditches. Blackboard: 'There's no such month as Rocktober'.
FAN DESK VERDICT A top-shelf entry. Not quite canon, but you’ll be quoting it all week — the fan desk says don’t skip.
The Simpsons S20E03 (“Double, Double, Boy in Trouble”) first aired on October 19, 2008.
In the US, The Simpsons season 20 — including this episode — is available on FX, Hulu, Disney+, fuboTV, DirecTV On Demand, Spectrum On Demand, YouTube TV, FOX One Amazon Channel, Hulu on Disney+, Amazon, Fandango at Home, and AppleTV.
Guest stars include Joe Montana (Joe Montana (voice)).
The Simpsons S20E03 (“Double, Double, Boy in Trouble”) was directed by Michael Polcino and written by Bill Odenkirk.
Fans rate The Simpsons S20E03 (“Double, Double, Boy in Trouble”) 8.1/10, which puts it in the great tier for The Simpsons.