A classic TV commercial once asked, "How many licks does it take to get to the center of a Tootsie Roll Tootsie Pop?" The narrator claims, "The world may never know" (Tootsie Roll 2012), but an Internet search returns a multitude of answers, some of which include rigorous systematic approaches by academics to address the question. These answers vary wildly: 144, 252, 364, and 411, to name a few (Tootsie, Scientific Endeavors, 2014). Mr. Owl, featured in the commercial, says three licks. Wolfram Alpha provides a different answer: 3481. The company's position on the question acknowledges the role of variables: "It depends on a variety of factors such as the size of your mouth, the amount of saliva, etc. Basically, the world may never know" (Tootsie Roll Industries 2016a). A teacher of statistics could develop a data set based on these answers; but with so many variables, this may not be the type of question that could be easily answered in a classroom. In this article, the authors consider another interesting feature about Tootsie Pops that students can investigate with statistical methods. Tootsie Roll Tootsie Pop wrappers feature drawings of children engaged in various activities, including sailing, horseback riding, playing baseball, roller skating, and so on. The image of "Chief Shooting Star" shows a boy, dressed in a Native American headdress, aiming a bow and arrow at a star. The investigation that the authors developed considers the proportion of all Tootsie Pop wrappers that contain a complete image of Chief Shooting Star. Stated another way, what is the probability of getting a wrapper with a complete image of Chief Shooting Star? A bibliography is included.