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Published 22:15 30 Oct 2016 GMT
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During the show's golden age, the character - voiced by Frasier star Kelsey Grammer - appeared in fewer than a dozen episodes and stole the show in each one. He would crop up again and again as The Simpsons has carried on for season after season, but let's not talk about that.
For many, his crowning moment involved him stepping on a succession of rakes, while his campaign for election as Springfield mayor was pure evil genius.
Hell, he's even a huge musical theatre aficionado, reeling off the entirety of HMS Pinafore in one fell swoop.
Robert Underdunk Terwilliger is one of TV's finest villains, and goes down as one of Grammer's career-defining roles alongside Dr Frasier Crane.
Which is why we were instantly won over by the actor's choice of Halloween costume.
https://twitter.com/dailysimpsons/status/792736799462268928
Not only is the hair and yellow face paint spot on, but it's good to see that the 61-year-old didn't phone in the rest of the outfit.
All of Bob's trademarks are there - green t-shirt, blue trousers and brown shoes.
It's tough to see from here, but we hope the shoes were big enough to accommodate the character's unusually large feet. And of course we trust that he got 'Die Bart Die' tattooed on his chest in preparation.
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