A few years later, using a family inheritance to pay for the trip, James moved to London and recorded some music demos. Kortchmar then introduced James to Peter Asher, who was head of A & R for the Beatles’ record label, Apple Records. Impressed by James’ demo, Asher passed it along to Paul McCartney and George Harrison, who were equally as moved by James’ voice and guitar playing. James became the first non-British artist to sign with Apple Records. He later hired Asher to be his manager.

James’ first self-titled studio album was recorded and released in 1968. It featured songs like “Carolina in My Mind,” “Something in the Way She Moves” and “Circle Round the Sun.” While recording the album, James underwent treatment for his use of drugs like heroin and meth. Apple Records released the record in both the US and the UK but due to James’ hospitalization, it wasn’t promoted well and sales were very poor. In 1969, James signed a new record deal with Warner Bros. Records. This turn of events likely helped him reach a point in his career where tickets to his shows were selling out and he was becoming a household name in the music world.

Just three short years after signing with Warner Bros., James achieved a feat that many seasoned musicians only dream of: he won his first Grammy Award for Best Pop Vocal Performance, Male, for the song “You’ve Got a Friend.” In total, he has won five Grammy Awards. His first song to hit #1 was “You’ve Got a Friend,” written by Carole King. This milestone followed the 1970 success of “Fire and Rain,” which helped catapult his career forward even more.