The original "Lollipop" by Ronald & Ruby (1958)

The Chordettes' big 1958 hit "Lollipop" continues to be a familiar and popular song a half-century after its release. It has been featured in numerous movies and television shows, including Stand By Me, CSI: Crime Scene Investigation, Whip It, Chicken Little, and The Simpsons. It has appeared in commercials for Dell computers and Life Savers candy. But few listeners are familiar with the story behind the song and its original version by the interracial duo Ronald & Ruby. Today on Music Weird, we'll look at Ronald & Ruby's original "Lollipop" and why it didn't become the familiar version of this instantly recognizable song.

"Lollipop" was written by Beverly Ross and Julius Dixson. Ross was a young, white, Jewish songwriter from New York, and Dixson was an older black songwriter and record label executive. The two of them had previously written Bill Haley's 1954 hit "Dim, Dim the Lights."

"Lollipop" was a sure-fire hit—it was infectious, memorable, and suggestive. It had the sound of a guileless children's song but also had some sexual innuendo, like many of the later bubblegum hits of the '60s and '70s. (Ross told Village Voice in 1958, "In this country it is taboo to express sexuality, and our adolescent population is very inhibited. The music brings some outlet to them. They need this. It is a medium in which they can express themselves....")

Beverly Ross

In her 2013 memoir I Was the First Woman Phil Spector Killed!, Ross says that she was inspired to write "Lollipop" after Dixson (she spells his name "Dixon") showed up at a songwriting session with a story about his daughter getting a lollipop stuck in her hair. Ross takes credit for most of the song, saying that she wrote the "first verse, hook, chorus ... and bridge within moments." She also takes credit for the way that the harmonies in the song build, because Dixson, in her words, "wrote Harlem cabaret blues with four chords, and never ventured into this genre...."

After Ross and Dixson wrote the song, Ross took it to a couple of song publishers, but they turned her down. She was mystified, because she thought that the song had obvious commercial appeal. So she persisted and took it to song plugger Arnold Shaw, who was more enthusiastic. "That's a smash," Shaw said. Shaw, in his 1974 book The Rockin' 50s, said that he was "so flipped by the rhythm ballad" that he had his secretary "instantly phone a recording studio and book time ... to cut a demo." 

In the studio, Ross herself recorded the song with a 13- or 14-year-old African-American guy named Ronald Gumm, who was Dixson's neighbor. Ross was primarily a songwriter but could sing pretty well and later recorded an unsuccessful solo single for Columbia, "Stop Laughing at Me."

"Lollipop" was recorded with only guitar, bass, piano, and drums, because of the short notice. The entire session cost only $55, if you believe Shaw, or $27, if you believe Ross.

Shaw used the demo to pitch the song to labels, but Archie Bleyer at Cadence Records wanted to release Ross and Gumm's demo recording as a commercial single. Releasing this demo as a master presented a few problems, though. For one thing, Gumm wasn't under contract, so the recording couldn't be licensed. For another, Gumm was a minor, so any contract with him would have to be worked out with his parents. And finally, Ross and Gumm were an interracial duo, which the music biz didn't regard warmly at that time.

Shaw, still trying to place the song rather than the demo, took it to Steve Sholes at RCA Victor. But Bleyer was in a frenzy for the song, because his teenage daughter loved it—a certain indication that it would be a hit! Bleyer told Shaw that if he didn't have a licensing deal for the Ronald & Ruby recording by the next day, then he was going to record the song with the Chordettes. 

Bleyer didn't have a deal the next day, so he recorded the song with the Chordettes. Shaw didn't really care. He was a song plugger, after all, not an agent for unknown recording artists.

Nevertheless, Shaw went ahead and negotiated a deal with Steve Sholes so that RCA Victor could release the Ronald & Ruby demo as a single. Billboard must have thought that the single was hit material, because it said in its April 7, 1958, issue that buying the demo was a "wise move" on RCA's part. RCA's ads, one of which is pictured at the top of this page, featured cartoon depictions of the artists instead of photographs in order to sidestep the race issue. Ross claims that her mother was the one who suggested that the record be released pseudonymously "for safety reasons" so that Ross' name wouldn't be associated with an interracial single.

The Ronald & Ruby version wasn't a big hit. It peaked at #20 in Billboard and #63 in Music Vendor. In Cash Box, it was ranked at #2 on the pop chart, but that's because Cash Box lumped together all the versions of the song. 

Bleyer's version with the Chordettes was the one that really swept the charts. Shaw said that "Lollipop" was the fastest-breaking single of his career as a song plugger, but even at that, the Chordettes weren't able to knock the Champs' "Tequila" out of the #1 spot. 

Ronald & Ruby's version was successful enough to merit a follow-up single ("Lovebirds"), but the follow up was even less successful than the first single. Some sources say that Ronald & Ruby's television and radio appearances were canceled when the duo's interracial composition came to light, but if that were true, why would RCA release another Ronald & Ruby single? Because—supposedly—Ross was replaced by a black singer. The image below is said to be a photo of the all-black Ronald & Ruby. I don't know if that's true or not.

The alleged all-black incarnation of Ronald & Ruby

After "Lollipop," Ross had some other hits and notable songs, including Elvis Presley's "The Girl of My Best Friend," the Earls' "Remember Then," and Lesley Gore's "Judy's Turn to Cry," and then had a late-career renaissance as a Nashville songwriter in country music.