Conan O'Brien, a frequent writer behind the Simpsons, also guest starred on The Simpsons as himself during season five.
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Homer joins the neighborhood watch and tries to put an end to the Springfield crime wave.
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When Springfield legalized gambling, Robert Goulet guest starred as himself, set to perform at Mr. Burns' casino until Bart tricks him into performing at his tree house.
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Homer ends up having a mutual attraction to a co-worker, Mindy Simmons (Michelle Pfeiffer's voice), but ends up not cheating on Marge.
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When Bart joined "The Junior Campers," he never expected to get trapped on the ocean with Homer and Flanders.
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James Brown lent his voice to The Simpsons during a season five episode, "Bart's Inner Child."
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Marge and Ruth Powers try to escape the cops in Ruth's stolen car in "Marge on the Lam."
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Bart and Lisa discover that Mr. Burns is actually a vampire in "Treehouse of Horror IV."
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The Simpsons Quotes

(Picking out a Tuxedo for Bart. He doesn't look pleased with his puffy shirt tuxedo.)
Bart: (frowning) Isn't this shirt kinda gay?
Clerk: Last time I checked, pirates weren't gay.
Homer: Eww, how'd you check?

Wow, now I see why they call you Miss Hoover. You must have been vacuuming for an hour.

Bart