Tootsie Pops  are hard candy lollipops filled with chocolate-flavored chewy Tootsie Roll. They were invented in 1931 by Luke Weisgram, an employee of The Sweets Company of America. The company changed its name to Tootsie Roll Industries in 1966.
In addition to chocolate (the original flavor), Tootsie Pops come in cherry, orange, grape, raspberry, strawberry, watermelon, blue raspberry, pomegranate, and now banana flavors. Another release of Tootsie Roll Pops, named Tropical Stormz, features six swirl-textured flavors: orange pineapple, lemon lime, strawberry banana, citrus punch, and berry berry punch.
In 2003, sixty million Tootsie Rolls and twenty million Tootsie Pops were produced every day.
Tootsie Roll Pops are known for the catch phrase "How many licks does it take to get to the Tootsie Roll center of a Tootsie Pop?" In the original television ad, a boy poses the question to a cow, a fox and a turtle. Each one tells the boy to ask someone else, explaining that they'd bite a Tootsie Pop every time they lick one. Eventually, he asks an owl, who starts licking it, but eventually bites into the lollipop, much to the chagrin of the boy. 
This ad was created by Thomas W. Knutson, son of Robert C. Knutson. K&K Advertising Art in Minneapolis MN is currently operating as K&K Studios. During the 1970's Tom wrote many jingles and advertising copy for his father at K&K. Other notable clients during that period would include Mr. Charles M. Schulz, creator of the Peanuts cartoon, and Mr. Albinson of Albinson Reprographics, later known as Procolor. Bob was hired by Albinson straight out of high school in 1932, and later he and Joe bought the Art group from Mr. Albinson in 1941. Over the last 65 years K&K has produced cereal boxes, billboards, newspaper advertising, and many online (Internet) ads, and more. Please see the following links:    
While the original commercial is 60 seconds long, an edited 30-second version and 15 second version of this commercial are the ones that have aired innumerable times over the years. The dialogue to the 60-second version is as follows:
The 30-second commercial dialogue:
The over 15-second commercial only shows the boy and Mr. Owl, and a different narrator speaks the same above line, but without the scene showing the Tootsie Roll pops slowly disappearing, and with a different tune playing in the background. The question still stands unanswered.
After the commercial, Mr. Owl became the mascot for Tootsie Roll Pops, appearing in marketing campaigns and on the packaging.
In the 1990s, a new commercial was made featuring a boy asking a robot and a dragon how many licks it takes to get to the center .
In the early 1970s, Tootsie Pops were the initial lollipop of choice of the titular character in the TV series Kojak, and are seen prominently beginning in the December 12, 1973 episode "Hot Sunday" when Lt. Theo Kojak decides to favor them instead of cigarettes.
The tootsie pop comes in these 16 flavors:
At some point, a rumor began that the lollipop wrappers which bore three unbroken circles were redeemable for free candy or even free items like shirts and other items. The rumor was untrue, but some shops have honored the wrapper offer over the years, allowing people to "win" a free pop.
Another urban legend is that wrappers with the "Indian star" (bearing an image of a child dressed as a Native American aiming a bow and arrow at a star) were redeemable for free candy. Another legend is that the same wrapper gives you good luck for the rest of the day.
Some stores redeemed lollipop wrappers with the child aiming a bow for a free sucker. This was clearly up to the store owner, and not driven by the lollipop manufacturer.