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"Does anyone know where this gif is from?"
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Looks like it's from the old Models and Buckets segment on Jimmy Fallon, but I'm not sure exactly where to find the clip.
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TonyA
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It's definitely "Models and Buckets" - you can see the young lady dumper's legs in the background. Just about all of the scenes are on YouTube, many as compilations such as "All the Models and Buckets...."
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