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Captain Jack was a recurring caller since 2002 who affected various annoying characters, all of which spoke in fake, sometimes semi-racist accents. He tended to tell unending, non-sensical monologues with no natural pauses, making it impossible for Tom to get a word in edgewise. Captain Jack and all his iterations were purged from Best Show history after an incident in 2007 when he sent a child to deliver a cooler containing a dead fish to Tom while on the air.

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