Amy Winehouse Said She 'Didn’t Think She'd See 28' Before Tragic Death at Age 27, Close Friend Claims

Amy Winehouse may have known her time on Earth would be short.

According to the late singer's close confidant Dale Davis, who spoke with Winehouse mere hours before her shocking July 2011 death from an accidental alcohol overdose, she knew she would not be living past the age of 27.

"I talked to her at 11:30 p.m., three hours before she went to bed for the last time, and she was on good form," Davis, who met the "Valerie" vocalist in 2003 and later joined her band, recalled in a recent interview. "Amy said, 'Dale, I’ve just been watching myself on YouTube and I can sing, can’t I?' I replied, 'Of course you can sing! You’re the best' . . . you know."

"I’m glad she went to bed with that thought. She needed to appreciate she could sing because she was very humble," Winehouse's pal continued. "Even at her level, a person can never see it in themselves. They probably think, 'Is the adulation real or not?' But to me, Amy is the first star of the millennium."

Despite her everlasting memory, Dale admitted there was one comment she made that has continued to haunt him. "I was out with her two nights beforehand. And she used to ring my house regularly around that time to speak to my wife (now ex-wife) and son. However, she did tell my ex that she didn’t think she’d see 28," the musician noted.

Winehouse struggled with her addictions while rising to fame in the late 2000s. "She would be sober for five weeks and then she would relapse for three days ... whenever she relapsed I'd leave, because I was worried she would think I was supporting that,” the "Back to Black" vocalist's friend Tyler James claimed in a 2021 interview.

“So I'd leave and within two or three days she would say 'Tyler, come home,' and I would come back," he said.

However, despite James' efforts to help Winehouse, her addiction continued to have a stronghold on her. "I’d left. I had a massive argument with her because by this point, there were letters from the doctor saying if she drank any more, that she’d die,” he explained. “And I came in from one afternoon, after going out for a walk and she had a glass of wine in her hand."

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The Sun conducted the interview with Davis.