"Sylvia's Mother" was a 1972 single by Dr. Hook & the Medicine Show and the group's first hit song. It was written by Shel Silverstein, produced by Ron Haffkine and was highly successful in the United States, reaching #5 on the Billboard singles chart, as well as #1 in Ireland and #2 in the United Kingdom. It also spent 3 weeks at #1 on the Australian music charts, making it the 15th ranked single in Australia for 1972. It appeared on the group's first album, Dr. Hook.

"Sylvia's Mother" is autobiographical, with songwriter Shel Silverstein drawing upon his unsuccessful attempt to revive a failed relationship. Silverstein had been in love with a woman named Silvia Pandolfi, but she would later become engaged to another man and end up as a museum curator at the Museo de Arte Carrillo Gil, Mexico City. Desperate to continue the relationship, Silverstein called Pandolfi's mother, Louisa, but she instead told him that the love had ended.

The lyrics tell the story in much the same way: A young man, despondent and near tears after learning that Sylvia, with whom he'd had an earlier bad breakup, is leaving town, tries to telephone her to say one last good-bye, or at least try to get a suitable explanation as to why their relationship failed and maybe try to rekindle things. However, Sylvia's mother (Mrs. Avery) tells him that Sylvia is engaged to be married, and is trying to start a new life in Galveston. She asks the man not to say anything to her because she might start crying and want to stay. She tells the man Sylvia is hurrying to catch a 9 o'clock train. In an aside, she then tells Sylvia to "take your umbrella, cause Sylvie, it's starting to rain." Rain could be construed as a metaphor that the caller has begun to "weep" due to his despair at not being allowed to speak to Sylvia...you can hear it in Dennis Locorriere's singing. She then returns to the phone conversation, thanks the (unnamed) narrator for calling. The pathos lies in the singer's awareness that Sylvia is right there with her mother, Sylvia being unaware that he's the man on the phone. Throughout the phone conversation, an operator cuts in to ask for more money ("40 cents more for the next three minutes") to continue the call.

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