I always heard this Tootsie Pop indian story growing up in the 1970's. The rumor was that if you had a red Tootsie Pop wrapper with an indian shooting an arrow at a star, you could cash it in for a free Tootise Pop.
I found many of these wrappers over the years and never tried cashing one in. I think the fact that I found one so easily made me think it was bogus. Or I was just too lazy to have my mom drive me to the store to get a free 10-cent lollipop.
You'll probably see a lot of Tootsie Pops around the office after halloween (as people dump and trade their leftovers). Check it out, if you've never noticed the indian shooting the star.
Here's a Snopes article on the topic. The Tootsie Roll company received requests for redemption for bags of candy or Tootsie Pops. In 1982, they began replying by returning this story along with their letter.
By the way, Mr Owl was wrong. I think it only took me about 1 lick to get
to the center. My dentist just loves me now.