While attending Abraham Lincoln High School in Brooklyn, New York, Laurie wrote and recorded a number of demo records, including "Sunglasses" which Linda recorded with her friend Linda Yellin as the "Knott Sisters"; the song failed to chart.
Another of Linda's songs was an odd tale of a girl walking through a dark subway tunnel with her boyfriend Ambrose, who implores her to "just keep walking."[3] She recorded the number for Glory Records in late 1958 and took it around to radio stations, who liked the deep-throated Ambrose (which Laurie voiced herself) and bizarre non-sequiturs like, "We haven't got a color telephone."
"Ambrose (Part 5)" (despite the name, there were no parts one through four) entered the Billboard charts in January 1959 and peaked at #52 in March. (The flip side, "Ooh, What A Lover", also received some airplay.) The song's notoriety was enough to get young Linda on the February 10, 1959, edition of To Tell the Truth; only two of the four panelists correctly identified her. A follow-up, "Forever Ambrose", in which the pair leave the subway tunnel and Ambrose even sings, failed to hit the charts.
From 1960-64, she made a number of other recordings for various small labels: "Stay with Me" (Andie 5015); "Chico" (Keetch 6001); "Lucky" (Recona 3502); "Prince Charming" (Rust 5022); and "Stay-At-Home Sue" (Rust 5042), a musical rejoinder to Dion's "Runaround Sue." In 1962, Linda reconnected with Ambrose in "The Return of Ambrose" (Rust 5061).