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THE SIMPSONS · SEASON 20 · EPISODE 3

The Simpsons S20E03 Double, Double, Boy in Trouble

★ 8.1 · GREAT Oct 19, 2008 30 MIN FOX 1 GUEST STAR
Still from The Simpsons S20E03: Double, Double, Boy in Trouble

The episode in brief

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.

Who’s in it

GUEST STARS
SERIES REGULARS

Behind the camera

DIRECTED BY Michael Polcino
WRITTEN BY Bill Odenkirk

Where it sits in the season

TAP A BAR TO JUMP

Where to watch S20E03

US · NOVEMBER 2026
AVAILABILITY IS FOR THE SHOW; NOT EVERY SERVICE CARRIES EVERY EPISODE · LINKS MAY EARN US POPCORN MONEY
8.1
THE FAN VERDICT
Keeper. Goes straight in the rewatch rotation.

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S20E03 FAQ

When did The Simpsons S20E03 air?

The Simpsons S20E03 (“Double, Double, Boy in Trouble”) first aired on October 19, 2008.

Where can I watch The Simpsons S20E03?

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.

Who guest stars in The Simpsons S20E03?

Guest stars include Joe Montana (Joe Montana (voice)).

Who directed and wrote The Simpsons S20E03?

The Simpsons S20E03 (“Double, Double, Boy in Trouble”) was directed by Michael Polcino and written by Bill Odenkirk.

Is The Simpsons S20E03 a good episode?

Fans rate The Simpsons S20E03 (“Double, Double, Boy in Trouble”) 8.1/10, which puts it in the great tier for The Simpsons.

EPISODE FACTS
SEASONSeason 20
EPISODES20E03
AIREDOct 19, 2008
NETWORKFOX
RUNTIME30 min
DIRECTORMichael Polcino
WRITERSBill Odenkirk
FAN RATING★ 8.1
TMDB★ 6.2 · 29 votes
VERDICTGREAT
WHERE TO WATCH
Watch on FX→ Watch on Hulu→ Watch on Disney+→ Watch on fuboTV→ Watch on DirecTV On Demand→ Watch on Spectrum On Demand→ Watch on YouTube TV→ Watch on FOX One Amazon Channel→ Watch on FX→ Watch on Hulu on Disney+→
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