"Lollipop" is a pop song written by Julius Dixson and Beverly Ross in 1958. It was first recorded by the duo Ronald & Ruby—Ross herself was "Ruby"—and then covered more successfully by The Chordettes. Dixson's name is sometimes spelled "Dixon".

The song is a firm favorite amongst many performing barbershop music.

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 of the song with Ronald Gumm (or Gumps), a 13-year-old neighbor of Dixson, under the name Ronald & Ruby. Ross' 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 #20.

"Lollipop" was then covered in the United States by female vocal quartet The Chordettes whose version reached #2 and #3 on the Billboard pop and R&B charts, respectively. The song became a worldwide hit. The Chordettes' version reached #6 in the UK, where there was also a cover version by The Mudlarks which made #2.

Another successful version of the song was recorded by Bobby Vee in 1961.

The Argentine band Viuda e hijas de Roque Enroll had a hit in the mid-1980s using interpolations of the two most popular "Lollipop" songs: the Dixson and Ross version, and "My Boy Lollipop". Samples of the original Ronald and Ruby version were also used.

The song was also covered by children's entertainers Sharon, Lois & Bram, on their 1995 album Let's Dance!.

...
Wikipedia