Top Definition
An evil genius who has tried to kill; Bart Simpson; Selma Bouviere; Krusty the Klown (x2) and probably others. He has also attempted to blow up Springfield, but mended his ways twice, thrwarting his brothers plans to flood Springfield and helping homer find the man who was trying to kill him (Frank Grimes' son).
Sideshow Bob bears a grudge against the world.
by Mortenson January 30, 2004

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Only the most intelligent homicidial maniac ever. Created by Matt Groening... tried to kill Bart, Selma, Krusty... many people, actually. See above.
'AAAAAH! SIDESHOW BOB!' 'Oh, we've been through so much together... just call me Bob.' 'AAAAAAAAAAAAAH! BOB!'
by GizGaz August 05, 2005

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The Urban Dictionary Mug

Your favorite word on a white mug.

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One side has the word, one side has the definition. Microwave and dishwasher safe. Lotsa space for your liquids.

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The Urban Dictionary T-Shirt

Soft and offensive. Just like you.

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The Urban Dictionary T-Shirt

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Named after the Simpsons character due to the resemblance to his hair, this is when a cigarette is rolled and the finished product has an excess afro of tobacco poking out of the top.
Haha, look at Lauren's fag everyone, she's got a major Sideshow Bob goin' on there.
by TheKHeroine March 21, 2011

The Urban Dictionary Mug

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The Urban Dictionary Mug

Lotsa space for your liquids.

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The Urban Dictionary Mug

Your favorite word on a white mug.

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The Urban Dictionary Mug

One side has the word, one side has the definition. Microwave and dishwasher safe. Lotsa space for your liquids.

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The Urban Dictionary T-Shirt

Soft and offensive. Just like you.

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The Urban Dictionary T-Shirt

Smooth, soft, slim fit American Apparel shirt. Custom printed. 100% fine jersey cotton, except for heather grey (90% cotton).

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Sideshow Bob existed before the Simpsons, the expression is a generic term for any insignificant person. More likely to be used by a cheeky mate or a toxic friend rather than an enemy.
Who's that loser she's going out with, some sideshow Bob, no idea.
by mongrelbeast January 01, 2008

The Urban Dictionary Mug

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The Urban Dictionary Mug

Lotsa space for your liquids.

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The Urban Dictionary Mug

Your favorite word on a white mug.

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The Urban Dictionary Mug

One side has the word, one side has the definition. Microwave and dishwasher safe. Lotsa space for your liquids.

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The Urban Dictionary T-Shirt

Soft and offensive. Just like you.

Buy the t-shirt

The Urban Dictionary T-Shirt

Smooth, soft, slim fit American Apparel shirt. Custom printed. 100% fine jersey cotton, except for heather grey (90% cotton).

Buy the t-shirt