Oprah Winfrey's busy this week talking legacy, weight loss, more

Oprah Winfrey poses is a sequined silver and purple duster over a lavender satin pantsuit.

Dec. 13, 2023 7:39 PM PT

Oprah Winfrey has had a busy week. From being caressed by Drew Barrymore to shutting down Ozempic naysayers, and even lighting the Empire State Building, here’s everything Oprah managed to accomplish by Wednesday morning.

On Tuesday, Winfrey joined Barrymore, who earlier this year was was hailed the “millennial Oprah” for her intimate approach to talk-show hosting. Together they discussed Winfrey’s early days working in television, as well as Winfrey’s forthcoming musical film adaptation of “The Color Purple.” But all viewers could seem to focus on was the way Barrymore clutched Winfrey’s hand throughout the interview, stroking her arm as she leaned in to absorb her elder host’s pearls of wisdom.

Naturally, the internet did its thing. “Drew Barrymore needs some kind of therapy because there is zero reason to cling onto people like that & invade their personal space!” Milinda Smith posted on X. “Like, all that extra weirdness with Ms. Oprah Winfrey ?! Girl, no.”

But apparently Winfrey says “Girl, yes” when it comes to being caressed. “I was actually comforted by the stroking of my arm,” Winfrey told TMZ on Tuesday. “I was not uncomfortable at all. I’ve never seen or done that, but I thought it was endearing. Drew’s terrific, and I love that she is always herself.”

Winfrey is no stranger to widespread criticism, having taken jabs on myriad subjects, including her approach to interviewing over the course of her decades-long career at the forefront of daytime talk shows, as well as her fluctuating weight. As for the latter, this week she shut it down once and for all, addressing the recent rumors that she’d started using weight-loss medication such as Wegovy, Ozempic or Mounjaro.

“It was public sport to make fun of me for 25 years,” Winfrey told People for a cover story published Wednesday. “I have been blamed and shamed, and I blamed and shamed myself.”

Winfrey said that, early on in her career, she was on the cover of a magazine with a headline that read, “Dumpy, Frumpy and Downright Lumpy” but that she didn’t feel angry. “I felt sad. I felt hurt. I swallowed the shame. I accepted that it was my fault.”

The media mogul, who turns 70 next month, said weight fluctuations occupied five decades of rent-free space in her brain, “yo-yoing and feeling like ‘why can’t I just conquer this thing?’”

Winfrey — while confirming that she does now use weight-loss medication paired with lifestyle changes — said she realized she’d been blaming herself for her lifelong struggle with weight, rather than giving herself grace for having a predisposition that no amount of willpower could control. “Obesity is a disease. It’s not about willpower — it’s about the brain.

“The fact that there’s a medically approved prescription for managing weight and staying healthier, in my lifetime, feels like relief, like redemption, like a gift, and not something to hide behind and once again be ridiculed for,” she continued to the outlet. “I’m absolutely done with the shaming from other people and particularly myself.”

Winfrey, whose eponymous syndicated daytime talk show ran 25 seasons from 1986 to 2011, has appeared as a guest on many talk shows herself this week. Dressed head to toe in varying shades of purple to promote “The Color Purple,” which she executive produced (she also starred in the original film adaptation in 1985), Winfrey has spent recent days looking back, and looking ahead, while discussing her career.

She sat down with Sherri Shepherd on “Sherri,” whose Emmy-winning host, 56, told Winfrey that, before Shepherd had her own daytime talk show, she was an audience member on “The Oprah Winfrey Show” in 1989 or 1990. As Shepherd played the deep-cut television moment, the two had a good laugh about the full-circle moment and discussed the idea of legacy.

“I was 23 years old, Oprah, and I was in your audience,” Shepherd told Winfrey. “I remember to the day because … commercials come on in Chicago and it would be you. And you were like, ‘If you’ve been cheated on by your boyfriend, call up.’”

“And I was just sitting there eating White Castle and I heard you,” she continued. “‘If you’ve been cheated on, call this number.’ And I was like, ‘Ooh, I’m gonna call this doggone number, I’ve been cheated on.’ And I was in your audience for an episode called ‘Snoops.’”

Later in the interview, Shepherd asked Winfrey what her legacy meant to her.

“The word ‘legacy’ — I just want to leave you all with this — when I came back from opening my school in South Africa, and I said to Maya [Angelou] that the school is going to be my greatest legacy. Those girls are everything, and she said, ‘You have no idea what your legacy is going to be.’

“Because, she said, your legacy is never one thing. It’s every life you touch. And I pass that on to you,” she continued to Shepherd. “Because what Maya said to me that day in her kitchen, she said it’s every audience member, whoever came from wherever they came from, and they sat in an audience and they had an experience. They went home and they decided, I’m going to do better. I’m going to get a better job. I’m going to leave my raggedy husband. I’m gonna do whatever I need to do.”

Winfrey continued that “your legacy” is about every life you touch, “so it’s not one thing.”

The icon then passed the talk-show baton to Shepherd, saying, “For me to be able to see you, to sit in the seat of your life, on your own show, with your name on it: It is a passing-on.” Shepherd burst into a tear-filled squeal.

Meanwhile, Winfrey’s legacy was celebrated by the Smithsonian on Wednesday.

Smithsonian’s National Portrait Gallery unveiled Winfrey’s portrait, painted by Chicago-based artist Shawn Michael Warren, which featured Winfrey in a purple taffeta gown surrounded by lush greenery at her California home. The full-length portrait, commissioned for the museum’s permanent collection, will be on display on the museum’s first floor beginning Wednesday.

“As a global media leader, philanthropist, producer, actor, author and entrepreneur, Winfrey has made significant contributions to American popular culture, which earned her a place in the National Portrait Gallery,” reads a Smithsonian statement.

The portrait was revealed in an invitation-only ceremony Wednesday morning, with luminaries from television, publishing, business, arts, culture and Hollywood in attendance.

“Through her rise to fame as host and producer of ‘The Oprah Winfrey Show,’ Oprah demonstrated an unparalleled ability to connect with people and inspire them to become the best versions of themselves,” National Portrait Gallery Director Kim Sajet said. “Her vision and spirit deserve recognition in the nation’s Portrait Gallery.”

Somehow, with Winfrey jetting about to discuss legacy, disavow shame, snuggle with Barrymore and attend her Smithsonian portrait reveal, she still managed to make it New York City on Tuesday night to light the Empire State Building, you guessed it, purple. In tow were the film’s stars Danielle Brooks, Taraji P. Henson, Fantasia Barrino and director, Blitz Bazawule.

“This is bigger than anything we could dream,” Winfrey said. “We’re all so excited to be here to celebrate, and to have our movie, the reimagined ‘Color Purple,’ as an offering to the world.”

This week on Oprah: An icon’s legacy, weight-loss rumors, caresses from Drew B. and a Smithsonian portrait

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