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The Beatles icon met Winehouse at the European MTV awards in Liverpool in 2008, only three years before the singer died from alcohol poisoning at the age of 27.
Describing the meeting, which came on the same evening that he first met Kanye West, McCartney told GQ: “The other person I met at the same time was Amy Winehouse, walking down the corridor.
“And I knew she had a problem, and I ended up just saying hi, she said hi.”
McCartney then revealed his regret – admitting that he should have followed her to compliment the singer’s mercurial talent.
“Afterwards I thought I really should have just run after her—’Hey, Amy, listen, you’re really good, I really hope you…’ —and say something that broke through the despair,” he said.
“And she’d remember and think, ‘Oh yeah, I’m good, I’ve got a life to lead.’ But you always have those little regrets. Anyway, that was when I saw Kanye for the first time.”
Winehouse died from alcohol poisoning in July 2011 at her home in Camden Town, North London.
The wide-ranging chat made international headlines yesterday, after McCartney admitted to masturbating alongside John Lennon.
“What it was, was over at John’s house, and it was just a group of us,” he explained. “And instead of just getting roaring drunk and partying – I don’t even know if we were staying over or anything – we were all just in these chairs, and the lights were out, and somebody started masturbating, so we all did”, he explained.
McCartney also revealed how John Lennon once unsuccessfully attempted to convince him to drill a hole in his own skull.