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Vintage Mr. Owl How Many Licks Does It Take Tootsie Pop T-Shirt Size:2XL Everybody's running to get thisThis Tootsie Pop t shirt features an image of Mr. Owl about to lick the lollipop filled with a chewy Tootsie Roll. The shirt reads How Many Licks Does It Take? Animated commercials for Tootsie Pops first starting airing in 1969. A boy asked a cow, a fox, a turtle, and an owl how many licks it takes to get to the center of a Tootsie Pop. The owl licked the Tootsie Pop three times, then bit into it. The owl became the most popular commercial character