Like most of the early songs recorded by Dr. Hook & the Medicine Show, this was written by Shel Silverstein. Silversteen was a brilliant storyteller with a vivid imagination, but this story was real.
In the song, Sylvia's mother is Mrs. Avery, and while that wasn't her real last name, the rest of the story - exaggerated a bit - was true. Silversteen told Rolling Stone in 1972: "I just changed the last name, not to protect the innocent, but because it didn't fit. It happened about eight years ago and was pretty much the way it was in the song. I called Sylvia and her mother said, 'She can't talk to you.' I said, 'Why not?' Her mother said she was packing and she was leaving to get married, which was a big surprise to me. The guy was in Mexico and he was a bullfighter and a painter. At the time I thought that was like being a combination brain surgeon and encyclopedia salesman. Her mother finally let me talk to her, but her last words were, 'Shel, don't spoil it.' For about ten seconds I had this ego charge, as if I could have spoiled it. I couldn't have spoiled it with a sledge hammer."
The real Sylvia kept her secret to all but a few family and friends. Remarkably, it was a Dutch public television producer named Arjan Vlakveld who found not only Sylvia, but also Sylvia's mother. Arjan told Songfacts: "The search for Sylvia was a big coincidence. I was having a glass of wine in the garden of my brother. He had quests and there was an American woman who after I explained what kind of things I produced, told me the story about Sylvia and her mother, who she knew. It was an old story because it was about her mother working on a high school with 'Sylvia's Mother.' She was already old in the time of her story. She didn't knew if it was true but the woman had claimed ones that she was the mother in the song. I only had a few names to go on and ended up in a telephone conversation with Sylvia Pandolfi, who at that time was a museum director in Mexico City. ('Down Galveston way' in the song meant in real life that she was getting married to a Mexican and moving there).
So I asked her the question: Are you by any chance the Sylvia in the song 'Sylvia's Mother?' She was very surprised because nobody knew, it was a personal and family story, she never told anyone. I filmed the interview with her mother in Homewood, Illinois. The same house where she had the telephone call with Shell Silverstein, probably even the same telephone number. She was 95 years at that time."
Here is the segment on Sylvia and her mother.
The band had two lead singers: Ray Sawyer (with the eye patch) and Dennis Locorriere. It was Locorriere, then 20 years old, who sang on this one, delivering the vocal with sincere sorrow. Many of Shel Silverstein's songs for the band were works of comedy ("Roland the Roadie and Gertrude the Groupie," "The Cover Of Rolling Stone), and Dr. Hook had a bawdy stage show that wasn't to be taken seriously, so not everyone picked up that this was a serious song about heartbreak. "A surprising number of people thought it was a parody but I always saw it as a truly heartbreaking story and I did my best to portray the anxiety and sadness that I knew that poor guy in the phone booth would be feeling," Locorriere told Songfacts. Dr. Hook's next single, "Carry Me, Carrie," was another serious heartbreak song written by Silverstein.
Shel Silverstein was a popular author and songwriter, who wrote for both children and adults. He was a writer and cartoonist for Playboy magazine, and a best-selling author of children's poems. He wrote "A Boy Named Sue" for Johnny Cash and another hit song for Dr. Hook and the Medicine Show: "Cover Of The Rolling Stone." He died of a heart attack in 1999 at age 68.
After this song became a hit, audience members would sometimes throw coins at the band Rocky Horror-style at the line "40 cents more." This could hurt quite a bit, especially when they were launched from the balcony.
This was the first single released by Dr. Hook & the Medicine Show, who later became simply Dr. Hook. While they were playing bars in the New Jersey area, they got a gig appearing in the movie Who Is Harry Kellerman and Why Is He Saying Those Terrible Things About Me?, and signed with Columbia/CBS Records, which is the label that released the soundtrack for the film. "Sylvia's Mother" was their first single; it made the Hot 100 at #99 for one week when it was first released, but months later, after CBS (led by Clive Davis) started promoting it, it took off and became a hit.
After the band had been performing this song for a while, Shel Silverstein wrote a new version for them called "Sylvia's Father." Only the end of the song was different, with the last verse changed to:
Sylvia's father says Sylvia's pregnant and you went and made her that way.
Sylvia's father says you motherf--ker I'm gonna kill you someday.
At this point, Dennis Locorriere would do a rant about the no-good scoundrel that knocked up Sylvia. This version was never recorded.
In the UK, this was kept out of the #1 spot by Donny Osmond's "Puppy Love."