How Many Licks Does It Take Tootsie Pop T-ShirtThis 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