Everyone knows who Oprah Winfrey is, and likely, a fair amount about her. But somehow, listening to Oprah never gets less compelling, and we find ourselves learning something new every time we tune in. On the new Apple TV+ documentary series Dear…, out June 5, Oprah reflects on her momentous career path, and the moments of connection that pushed her to reach for what she wanted along the way. Told through a series of impassioned letters from viewers, the series explores the individual lives Oprah has touched — and how they’ve touched her right back. The series shows us that Oprah isn’t just driven because she’s fearless (although wow, is she fearless); she’s driven out of genuine love and compassion.
Oprah gets into details of her TV career that made us gasp — like the story about how her very first co-anchor tried to run her off the show, or the pushback she got for refusing to pit talk show guests against each other. But what this series makes crystal clear is that each of Oprah’s career choices along the way — not to mention her overwhelming determination — came from a desire to love and be loved, and a sense that she could build that for herself in television.
Describing the seminal The Oprah Winfrey Show and its incredible community of viewers, Oprah admitted that her compassion for others, which won her so much fame and success, was always tied to what she felt she lacked as a young girl.
“I ended up in life giving what I most needed for myself,” she explains. “Because I didn’t get the love that I believed I deserved, I used the platform to try to give it to every person I encountered. And the irony of it all is, for a little girl who grew up not feeling loved, I have felt really, truly embraced and loved by people I’ve never met.”
It’s safe to say the world loves Oprah right back, and the eye-opening moments of this docuseries will remind you why. Here’s what we learned about this icon from Dear…
She talked her way into skipping kindergarten
Oprah described walking into her kindergarten classroom and immediately sensing her classmates were on a different level from the education she’d already had.
“I remembering writing my kindergarten teacher Ms. New a letter,” she said. “‘I do not belong here.'”
She skipped to 1st grade after showing her teacher how many long words she could write, including “genesis,” “elephant,” and “hippopotamus.”
Barbara Walters was her idol
When she first started on TV, Oprah says she had no idea what she was doing — her only skills were speaking well and mimicking Barbara Walters.
“I show up on the air in Baltimore as a 22-year-old,” she says, “wanting to be like Barbara Walters, sitting like Barbara, trying to speak like Barbara…”
She was asked to have plastic surgery on her first TV job
“I’m paired with a co-anchor who doesn’t want me there, an elderly white man,” she recalls. “They didn’t like my hair. They actually asked me to have plastic surgery. So obviously, they were trying to make me look like somebody that I wasn’t. And it did not work.”
She confronted a white civil rights movement in 1987
In 1987, Oprah went to Forsythe, Georgia with The Oprah Winfrey Show to confront a community that had been all-white since 1912 and was in the midst of launching a white civil rights movement.
Oprah walked right into their town hall and interviewed them about their beliefs: “Walking into that room, I did not feel immediate hostility or danger,” she remarks. “A lot of them watched the show.”
One episode about cheating husbands changed her career
On The Oprah Winfrey Show show, the producers started bringing in couples and family members specifically to have them fight as entertainment. Oprah recalled one episode she’ll never forget — the one that made her realize she wanted to take the show in a totally different direction.
“There was a show with men who cheat and the producers were able to get a man to come on the show with his wife and his mistress,” she described. “The husband said to his wife during a live show…’well you know she’s pregnant,’ and he’s speaking of his girlfriend. And the pain and humiliation on her face…and I said, ‘never again.'”
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