While, we always thought that the debate was pointless, speculation over where Springfield is actually set has raged throughout the 18 years of the Simpson's existence. The creators in "Behind the Laughter" have insinuated that it is probably somewhere in Kentucky, but it was based largely on Portland, OR, where creator, Matt Groening, grew up. For the most part, we are content with Springfield being Anytown, USA, allowing the creators to make it whatever they want for a particular episode.
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Weekend Diversion: Night Of The Ponies