Lee made his first recordings in his hometown of Memphis for Tampa Records and Sun Records in 1957–58. He achieved his first chart success in 1962, when his composition “She Thinks I Still Care” was a hit for George Jones (later recorded by Elvis Presley, Connie Francis, Leon Russell and later Anne Murray as “He Thinks I Still Care”). Later that year, “Patches”, written by Barry Mann and Larry Kobler and recorded by Lee for Smash Records, rose to No. 6. The song tells in waltz-time the story of teenage lovers of different social classes whose parents forbid their love. The girl drowns herself in the “dirty old river”. The singer concludes: “It may not be right, but I’ll join you tonight/ Patches I’m coming to you.” Because of the teen suicide theme, the song was banned by a number of radio stations. However, it sold over one million copies and was awarded a gold disc.

Lee had a No. 14 hit in 1963 with a song he co-wrote, a conventional rocker, “I Saw Linda Yesterday”. In 1965, he returned to teen tragedy with “Laurie (Strange Things Happen)”, a song related to the urban legends known as the vanishing hitchhiker and Resurrection Mary.

After the 1960s, Lee devoted his efforts to country music performing and songwriting. His 1970s country hits as a singer include two remakes of pop songs, Delaney & Bonnie’s “Never Ending Song of Love” and Austin Roberts’s “Rocky” (another bitter-sweet song, written by Jay Stevens of Springfield, MO – a.k.a. Woody P. Snow), in addition to original songs such as “Angels, Roses, and Rain”, and “9,999,999 Tears”. He also co-wrote several songs with Bob McDill, including “Someone Like You” (by Emmylou Harris), “I’ve Been Around Enough To Know” (first recorded by Jo-El Sonnier in 1973, but would become a No. 1 hit in 1984 for John Schneider), and “The Door is Always Open” (by several artists, most notably by Dave and Sugar).

He was inducted into the Nashville Songwriters Hall of Fame in 1995. Lee is included as co-writer and singer on singer-songwriter Michael Saxell’s 2005 album Wonky Windmill on the song “Two Men”.