1784, lolly-pops "sweetmeats, soft candy," perhaps related to loll "to dangle" (the tongue) + pop "strike, slap." Or the first element may be northern dialectal lolly "the tongue." Meaning "hard candy on a stick" is from 1920s.
A pitch that is easy to hit: will they chuckle when out-of-shape lefties lob up lollipops? (1960s+ Baseball)