It has been years since Michael Jackson and Paul McCartney have been considered the best of friends (or even on speaking terms), but the King of Pop's death leaves the former Beatle sad and shocked all the same.

"I feel privileged to have hung out and worked with Michael," read a statement on McCartney's website this morning. "He was a massively talented boy man with a gentle soul. His music will be remembered forever and my memories of our time together will be happy ones.

"I send my deepest sympathy to his mother and the whole family and to his countless fans all around the world."

McCartney's superstar-meets-superstar friendship with Jackson was irreparably damaged when Jackson purchased the Beatles song-copyright catalog from Apple Records for $47.5 million in 1985—an asset that confused people forever after as to how Jackson ultimately became so financially insolvent.