Oprah Winfrey Was ‘Shocked’ She Didn’t Marry Paul McCartney

While growing up, Oprah Winfrey was among the many people harboring a crush on Paul McCartney. Unlike most of these people, though, she actually had the opportunity to meet McCartney. Winfrey interviewed McCartney on her show in 1997 and has seen him multiple times since then. She jokingly explained that, given the way her life has played out, she was a bit surprised that she never married the Beatle.

Oprah Winfrey said Paul McCartney was her childhood crush

In her lengthy and prolific career, Winfrey has met many celebrities. She found her 1997 interview with McCartney particularly nerve-wracking, though. She was out of her element, recording the show in New York instead of at Harpo Studios in Chicago. The more significant source of nerves, though, was that she was sitting down with someone she idolized in her youth.

“When I first interviewed Paul in 1997, I was so nervous,” she told Jerry Seinfeld in an interview, per Oprah.com. “We were live on a stage in New York, in front of a big audience, and I said, ‘I used to have your picture on my wall, and you were on the back of my cereal box. As I was eating breakfast, I’d wonder, “Is Paul eating his cereal, too? Is he thinking about me?”‘ Oh, well.”

Despite her nerves, she said that she was surprised she never married the former Beatle. She’d achieved everything else she wanted to do. 

“I’m really shocked that I never married Paul McCartney,” she told Extra. “As a kid growing up I had every single dream of mine that I wanted to come true, to come true, except I never married Paul McCartney.”

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The pair reunited at the Kennedy Center Honors

Several years later, McCartney and Winfrey were both honorees at the 2010 Kennedy Center Honors. The pair sat together alongside fellow honorees Merle Haggard, Jerry Herman, and Bill T. Jones as President Obama spoke about their accomplishments.

“Although the honorees on this stage each possess a staggering amount of talent, the truth is, they aren’t being recognized tonight simply because of their careers as great lyricists or songwriters or dancers or entertainers,” Obama said, per Billboard. “Instead, they’re being honored for their unique ability to bring us closer together and to capture something larger about who we are — not just as Americans, but as human beings.”

Oprah Winfrey warned Paul McCartney against working with Kanye West

Several years later, McCartney and Winfrey were friendly enough that she warned him against working with Kanye West on the song “All Day.” Winfrey didn’t think McCartney should appear on a song in which West used the n-word.

“The lyrics…use the n-word a lot,” McCartney told BBC Radio 4. “The thing was about that when I got it, and people heard it, quite a few people said, ‘You can’t be connected with this. You know, there’s like 40 n-words.’ And people are gonna say, ‘Hey, man. You know, you shouldn’t do that.’ And people like Oprah, who are a little conservative about that stuff, she says, ‘You shouldn’t do it. Even Black people shouldn’t use that word.’ I said, ‘Yeah, but it’s Kanye,’ and he’s talking about an urban generation that uses that word in a completely different way.”