Leo Hirshfield was looking around for a name for the new confection he was making from a recipe he'd brought over from Europe in 1896. He choose the name of his 6 year old daughter, Clara, whose nickname was Tootsie.
Tootsie Rolls were the first penny candy to be individually wrapped in paper. They were one of the top choices of children who only had a few pennies to spend on satisfying a sweet tooth.
In the 1930s, the first soft-centered lollipops, Tootsie Pops, were sold. The hard candy on the outside covered the Tootsie Roll center.
During World War II, Tootsie Rolls were favored by soldiers because they could be kept in pockets and barracks bags without melting. They were also a great source of quick energy.
In the late 1940s, Tootsie Rolls were advertised on the comic pages of many Sunday newspapers. The main cartoon character was Captain Tootsie who was a Superman-like hero who took kids on various adventures.
Urban Legend... A Tootsie Pop wrapper with a picture of an Indian shooting an arrow at a star on it can be redeemed with Tootsie Roll Industries for a free bag of candy. Sorry, about 30% of the wrappers have the Indian and Tootsie has never had such a contest.