The first individually-wrapped and sold penny candy in the United States was the Tootsie Roll, which was introduced in 1896. The candy was invented by Leo Hirshfield, an Austrian immigrant living in New York City. He named the candy after his daughter, whose nickname was "Tootsie."
The second wrapped penny candy to be introduced was Sweethearts candies, which were sold by the Civil War candy company Necco Wafers. Hershey's Kisses became the first chocolate penny candy when they entered the market in 1907. Other popular penny candies included bottle caps, licorice, candy corn, bubble gum and jaw breakers. The term "penny candies" refers to the fact that the pricing was originally a penny per piece of the candy, even though much of it was sold in bulk by the pound, rather than by the piece.