He started his own career in the candy business at a small shop or factory in New York City in 1896.

Tootsie Roll's principal supplier of paper boxes, Joseph Rubin & Sons of Brooklyn, was concerned about losing an important customer and decided to acquire the troubled company.

He guided the company successfully through the difficult war years during which vital raw materials were in short supply.

In the 1970s, artist Herb Trimpe is believed to have modeled the original costume for the Marvel Comics character Doc Samson partly on Captain Tootsie's uniform.

[18] In 2019, artist/writer Erik Larsen used Captain Tootsie as one of several older comic book characters in the public domain as part of his Savage Dragon series.

The jingle was sung by a nine-year-old, Rebecca J. Weinstein, and 13-year-old David Johnson, the children of jazz musicians and friends of the song's composer.

[21] The current U.S. ingredients of a Tootsie Roll are: sugar, corn syrup, partially hydrogenated soybean oil, condensed skim milk, cocoa, whey, soy lecithin, and artificial and natural flavors.

Known as Tootsie Fruit Chews, flavors include cherry, orange, vanilla, lemon, and lime.

They also offer a special Mega Mix bag that includes specialty flavors, green apple, blue raspberry, and grape.

Tootsie Frooties come in numerous different fruit flavors, including strawberry, blue raspberry, grape, green apple, banana berry, smooth cherry, fruit punch, pink lemonade, root beer, cranberry, blueberry, watermelon, and the newest, mango.