Craig Douglas, the Isle of Wight born singer whose cover of "Only Sixteen" topped the UK singles chart in 1959 and outsold Sam Cooke's own version of the song there, died at his home on the island on September 4, 2026. He was 85. His family said he died peacefully, surrounded by family, according to the Isle of Wight County Press.

Born Terence Perkins on the Isle of Wight, he worked as a farmhand at Bill Strickland's Farm in Calbourne and then as a milkman, a job that gave him a nickname that outlasted his chart career: the Singing Milkman, per the Isle of Wight County Press.

His path into music opened in November 1957, when he was sixteen. His mother entered him into a talent contest at the Medina Cinema in Newport, and he won it singing Pat Boone's "Love Letters in the Sand." The win reached the manager and record producer Bunny Lewis and his wife, Janique Joelle, who persuaded the teenager to turn professional and gave him the stage name he performed under for the rest of his life. Within months he had a week's residency at the Empire Theatre in Portsmouth, billed as "The Boy with the Golden Voice," and an appearance on BBC television's "Six Five Special" alongside Cliff Richard and Joe Brown.

Signed to the Top Rank label, Douglas released a run of cover versions of American hits, nine of which reached the UK Top 40. The biggest was "Only Sixteen," recorded at Abbey Road Studios and released in 1959, which reached number one and outsold Cooke's original in Britain, according to The News International. NME voted him Best New Singer that same year. He starred in the 1962 film "It's Trad, Dad!" alongside Helen Shapiro and Chubby Checker, and headlined a UK stage tour on which a little known Liverpool group called the Beatles appeared as a support act, one of the group's first major tours, not long before Beatlemania rewrote the British charts he had briefly topped. His last Top 40 single, "Town Crier," reached number 36 in February 1963.

Douglas kept performing long after the hits stopped, playing nightclubs and cruise ships for decades. In 2010, by then using a wheelchair, he took the stage at a benefit concert for the Amersham Rock 'n' Roll Club, and he released a final studio album, "The Craig Douglas Project," in 2011. He never married or had children, a choice he later called a regret. "I didn't get married to start with, which was a shame. I would have liked to have had a couple of children, but if I had, I'd miss them like mad while I was away," he said in a 2024 interview, quoted by AOL.

One record ties Douglas to the history books more than any other, the 1959 chart topper that beat an American original at its own game, but the fuller shape of his career says more about British pop before the Beatles remade it: a farm hand and milkman who became a headline act, shared a stage with the group that would eclipse him, and kept singing in smaller rooms for another half century after the charts moved on. The Isle of Wight, where he was born and where he returned to live out his final years, counted him as its own homegrown star to the end.