Bobby Vee, best known for hits including Rubber Ball, Take Good Care of My Baby and The Night Has a Thousand Eyes, has died at the age of 73.
Vee released more than 25 albums during his career, retiring in 2011 after being diagnosed with early-onset Alzheimer's disease.
Vee's son Jeff Velline said the singer died peacefully surrounded by family on Monday.
It was "the end of a long hard road", Mr Velline said.
He described his father as "a person who brought joy all over the world", adding: "That was his job."
Young Bobby Vee
Vee's big break came about in 1959 at the age of 15 when he filled in for Buddy Holly after the singer's death in a plane crash.
Ritchie Valens and The Big Bopper were also killed in the accident in Iowa, along with the pilot, Roger Peterson.
A call went out for local acts to replace Holly at his scheduled show at the Moorhead National Guard Armory. Vee and his band, which had only formed two weeks previously, volunteered.