 Connecticut was first at many things. When was the first lollipop machine used? Oh, man. Lollipop. Lollipop. Oh, lolly lolly pop. We need a machine to make lollipops? 1930s, I would guess. I don't know. Yeah, it has to be somewhere around the 20s and 30s. The Industrial Revolution. It could be the 1880s. Yeah, 1880, 1890. The machine? Yeah.