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Tie Dye Mr. Owl How Many Licks Tootsie Pop T-Shirt breadcrumb-cyndi-lauper shows Darth VaderThis Tootsie Pop t shirt features an image of the famous animated owl about to lick the lollipop filled with a chewy Tootsie Roll. The shirt reads, "How many licks?" 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