Craig Douglas, the British singer who achieved early success as a teenage balladeer before being overshadowed by the rise of the Beatles, died on September 4 on the Isle of Wight at the age of 85.

Born Terence Perkins on August 13, 1941, in Newport, Isle of Wight, Douglas emerged from humble beginnings as one of nine children in his family. Before his music career took off, he worked as a milkman on the Isle of Wight, earning the moniker “the singing milkman” due to his melodious voice heard during his milk rounds. His early break came after winning a local singing competition at the Medina Theatre, where the venue’s owner, Colonel Britten, took interest and connected him with Bunny Lewis, a noted agent who helped reshape Douglas’s career, including the adoption of his stage name.

Douglas first recorded in 1958 with Decca Records, a label historically known for rejecting the Beatles. His debut, “Sittin’ in a Tree House,” written by Burt Bacharach and Hal David, garnered some attention, but it was his covers of contemporary American hits that brought him chart success. He gained widespread recognition in 1959 with “Only Sixteen,” originally by soul singer Sam Cooke, which Douglas transformed into a pop ballad featuring distinctive whistling. The song reached number one on the UK charts, outpacing even Elvis Presley’s sales at the time and earning Douglas the distinction of best new singer by the New Musical Express. Additional hits included “Pretty Blue Eyes” and “Heart of a Teenage Girl.”

Despite his initial popularity, Douglas’s style was soon eclipsed by the rapidly changing music scene of the 1960s. The Beatles, who notably supported him during his 1962 performances at the Liverpool Empire, quickly redefined British pop and rock music. Douglas acknowledged that his clean-cut ballad style, focused on romantic themes, was out of step with the emerging rock and roll sound. Reflecting on this shift, he expressed that adapting to the new style was not something he felt able to do.

In 1962, Douglas appeared in two films — “It’s Trad, Dad!,” directed by Richard Lester, and the crime thriller “The Painted Smile.” That same year, he toured with the Beatles as his backing band before their breakthrough fame. However, as the Beatles rose to prominence, Douglas’s own popularity declined, and by the mid-1960s he had largely stepped back from the music industry.

Following his peak years, Douglas continued performing intermittently, including chart success in Australia, entertaining troops in Vietnam with Beatles covers, and working as a cabaret singer and cruise ship performer. Despite his stage success, he experienced personal challenges, including the end of several romantic relationships and never marrying. He later described feeling isolated upon returning to the Isle of Wight decades later.

Douglas’s career was emblematic of the stark transformation in British popular music from the late 1950s into the 1960s, illustrating the fleeting nature of early pop stardom amid shifting cultural trends.