The song originated when Julius Dixson was late for a songwriting session with Beverly Ross. He explained that his daughter had gotten a lollipop stuck in her hair, and that had caused him to be late. Ross was so inspired by the word "lollipop" that she sat down at the piano and produced a version of the song on the spot. Beverly Ross recorded a demo with Ronald Gumm (or Gumps), a 13-year-old neighbor of Dixson, under the name Ronald & Ruby. Ross's mother insisted that she use a pseudonym for safety reasons, because they were an interracial duo.
RCA got hold of it and Dixson, who owned the master and had produced the demo, agreed to let them release it. Ronald and Ruby's version rose up the chart, reaching No. 20.
"Lollipop" was then covered in the United States by female vocal quartet The Chordettes. The Chordettes' version featured the sounds of rhythmic hand claps heard at the beginning, and a distinctive popping sound created by one of the Chordettes putting her finger into the mouth and flicked out. Their version featured also a male chorus singing the "Boom Booms", following the isolated popping sounds. The Chordettes version reached No. 2 and No. 3 on the Billboard pop and R&B charts, respectively. The song became a worldwide hit. The Chordettes' version reached No. 6 in the UK, which is their highest charting song in the UK.