According to Julius Dixson, the song originated when he 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. As in many rock and roll songs, the lyrics contain some hints and innuendos relating to sex. 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. ==The Chordettes version==