Oprah Winfrey has built an empire on authenticity and vulnerability, but even the most successful media figures look back on some decisions with a wince. In a recent candid moment, the 72-year-old billionaire called one of her late 1990s ventures a career mistake: her musical track "Run On." The revelation came during an appearance on Keke Palmer's podcast, "Baby, This Is Keke Palmer," where Palmer playfully sang a few lyrics from the song. Winfrey's reaction was immediate and honest.
"Girl, please. Okay, that is one of the mistakes of my career," Winfrey said, prompting Palmer to defend the track. Palmer insisted, "It's no mistake! We love it." But Winfrey stood firm: "It is a mistake." She then explained the origin of the song, which served as the theme for The Oprah Winfrey Show in the late '90s. At the time, she was wrestling with whether to end the show or continue. After a spiritual moment, she decided to keep going and thought the old spiritual "Run On" would be a fitting theme.
"So what had happened was, I was trying to decide, 'Am I gonna end the show or not end the show?' And then I had a little talk with Jesus, and Jesus said, 'You gotta keep going.' And so I said, 'You know, there's this song. It's an old spiritual,'" Winfrey recounted. She even sang a bit before joking about her own vocal limitations. "And then we realized, I can't sing, even though I took the singing lessons," she confessed. Palmer tried to soften the blow, but Winfrey doubled down: "It was bad. You know it was bad. It was bad. You're just saying that 'cause you're looking at me right now. It was bad. It was pretty bad."
The media mogul explained that she thought a church choir could salvage the track, but even backup vocals couldn't rescue it. Palmer suggested, "Sometimes backup vocals will do that," to which Winfrey replied, "Sometimes. Didn't work this time." The exchange was lighthearted, but it highlighted Winfrey's self-awareness and willingness to laugh at her own missteps.
A Career of High Stakes and Public Scrutiny
Oprah Winfrey's career is defined by triumphs—from launching The Oprah Winfrey Show in 1986 to creating OWN, her cable network, and becoming a global philanthropist. But behind the accolades lie moments of vulnerability, including a few projects that didn't land as intended. The "Run On" song is far from the only misstep; Winfrey has often spoken about other regrets, such as not leaving her talk show earlier or the backlash from promoting certain fads.
However, her willingness to discuss these mistakes openly is part of what endears her to millions. In the same podcast appearance, Winfrey also revisited one of the most talked-about interviews of recent years: her 2021 sit-down with Prince Harry and Meghan Markle. That interview, which aired on CBS, drew global attention for the couple's revelations about royal life, including allegations of racism and lack of support.
During a subsequent interview with Vanity Fair on July 21, Winfrey reflected on a specific moment from that conversation when she asked Markle, "Were you silent or were you silenced?" The question, accompanied by a distinctive hand motion, became an instant meme. Winfrey admitted she had never used that gesture before or since. "I don't think I've done it since. I don't know where the hell that came from," she said. She explained the reasoning behind the query: "I wanted to be clear because, 'Was she silenced? Were people telling her not to talk?' That's why I said that. I said it for clarification because I didn't want later to hear, 'Well, no, it wasn't that. It really was that I was silenced. They wouldn't let me talk.' So it was all for clarification."
This level of introspection is characteristic of Winfrey, who has long used her platform to explore human psychology, growth, and the messiness of life. Her ability to turn a mistake into a teachable moment—or at least a humorous anecdote—is a skill she has honed over decades.
The Cultural Context of the '90s and Oprah's Evolution
To understand why Winfrey's song misstep resonated, it's helpful to look at the cultural landscape of the late 1990s. At that time, many talk show hosts were branching into music. Phil Donahue had attempted a singing career, and even Geraldo Rivera dabbled. Oprah's attempt was part of a trend where personalities sought to expand their brands. However, unlike her daytime rival Rosie O'Donnell, who released successful albums, Oprah's musical foray was met with less enthusiasm. Critics described the song as earnest but forgettable, and it quickly faded from public memory—until now.
The decision to use "Run On" as a theme song also reflected a spiritual shift in Winfrey's public persona. During the '90s, she began incorporating more faith and spirituality into her show, inviting guests like Deepak Chopra and Eckhart Tolle. The song, an adaptation of the traditional spiritual "Run On for a Long Time," was meant to convey perseverance. But as Winfrey now admits, the execution fell short.
In retrospect, the song's failure may have been a blessing in disguise. It forced Winfrey to double down on what she did best: conversation and connection. The Oprah Winfrey Show continued to dominate ratings, and she eventually transitioned to OWN, where she focused on original programming that emphasized personal stories and empowerment.
Lessons in Resilience from a Media Icon
Oprah's willingness to air her career laundry is refreshing in an era of curated perfection. It reminds us that even the most accomplished individuals make choices they later regret. What sets Winfrey apart is her ability to pivot and learn. After the song's release, she didn't attempt another musical project; instead, she leveraged her influence to produce films, launch a magazine, and establish a leadership academy for girls in South Africa.
The Keke Palmer podcast episode also touched on how Winfrey views failure broadly. She has often said that her biggest lessons came from setbacks. For example, the backlash she faced from the beef industry in 1996 after she revealed she had stopped eating beef due to mad cow disease concerns could have derailed her career. Instead, she stood her ground and eventually settled a defamation lawsuit filed by Texas cattle ranchers (though she continued to speak openly about food choices). Similarly, the short-lived Oprah Winfrey Network launch struggled initially, with low ratings and financial losses. But through persistence and strategic programming shifts, OWN became profitable by 2014.
"You know, every mistake I've made has taught me something," Winfrey said in a 2019 interview. "If I hadn't made them, I wouldn't be where I am." That philosophy underpins her latest admissions about "Run On" and the Meghan Markle interview.
The Power of Owning Your Flaws
In an age where celebrities often hide behind PR teams, Oprah's raw honesty is a breath of fresh air. Her admission about "Run On" was not just an act of self-deprecation; it was a reminder that success is not linear. She could have simply let the moment pass, but instead, she engaged in a playful back-and-forth with Palmer, showing that she is comfortable in her skin.
The exchange also highlights the importance of having trusted collaborators who can laugh with you. Palmer, a younger media star in her own right, clearly adores Winfrey and wasn't about to let her wallow in regret. Their rapport underscores a generational passing of the torch, as Palmer represents the new wave of multi-hyphenate entertainers who value authenticity over polish.
For fans, hearing Oprah call something "pretty bad" is endearing. It humanizes a woman who has been a beacon of empowerment for so long. And it invites everyone to embrace their own missteps, whether a failed project or a questionable haircut.
The story of "Run On" may be a footnote in Oprah's storied career, but it speaks volumes about her character. She didn't need to release that song—she already had a hit talk show. But she took a risk, it didn't work, and today she can look back and laugh. That's the kind of grace that keeps audiences coming back for more.
Meanwhile, her analysis of the Meghan Markle interview offers a behind-the-scenes look at her journalistic instincts. She wanted precision in a conversation that could have been easily misconstrued. The hand gesture may have been spontaneous, but the intention was sharp: to get to the heart of what Markle experienced. It's that same careful consideration that has defined Oprah's best interviews, from Tom Cruise's couch-jumping to Lance Armstrong's confession.
As Oprah continues to evolve—now with a robust presence in podcasting, a weight-loss company partnership, and a growing family with her dogs and partner Stedman Graham—she remains a figure who is not afraid to admit when she misses the mark. In doing so, she gives everyone permission to do the same.
Source:MSN News