lollipop n.

mid-14c., lollen "to lounge idly, hang loosely;" late 14c., "rest at ease" (intransitive), a word of uncertain origin; perhaps related to Middle Dutch lollen "to doze, mumble," or somehow imitative of rocking or swinging. Specifically of the tongue from 1610s. Also in extended form lollop (1745). Related: Lolled; lolling. As a noun, from 1709. Lollpoop "A lazy, idle drone" ("Dictionary of the Vulgar Tongue") is from 1660s.

"a hit with a smart, explosive sound," c. 1400, of imitative origin. Meaning "effervescent carbonated beverage" is from 1812.

A new manufactory of a nectar, between soda-water and ginger-beer, and called pop, because 'pop goes the cork' when it is drawn. [Southey, letter, 1812]

Sense of "ice cream on a stick" is from 1923 (see popsicle). Meaning "the (brief) time of a 'pop'" is from 1530s. Pop goes the weasel, a country dance, was popular 1850s in school yards, with organ grinders, at court balls, etc.

short for lollipop, 1854. Also, in mid-20c. British slang, "money."