'It Was Bad': Oprah Winfrey Reveals the Career Decision She Wishes She'd Never Made

For someone who built one of the most successful careers in television history, you would think Oprah Winfrey had very few regrets.

Turns out, she does. And it involves singing.

During a candid conversation on Keke Palmer's podcast, the media mogul burst into laughter while looking back at what she now calls "one of the mistakes" of her career—recording the theme song for The Oprah Winfrey Show in 1998.

When Palmer began singing a line from the gospel-inspired track Run On, Oprah didn't miss a beat.

"Girl, please," she laughed. "That is one of the mistakes of my career."

Palmer quickly came to her defence, insisting the performance wasn't nearly as bad as Oprah made it sound.

Oprah wasn't buying it. "You know it was bad. You're just saying that because you're looking at me," she joked. "It was pretty bad."

The confession surprised many because the decision wasn't impulsive. Oprah revealed that she had seriously considered ending The Oprah Winfrey Show at the time. During that period of uncertainty, she said she had what she described as "a little talk with Jesus," after which she decided to continue.

Inspired by an old spiritual, she chose Run On as the show's new theme and even took singing lessons before recording it. She believed she could pull it off.

Reality had other plans. Despite the lessons—and even with a church choir brought in to strengthen the recording—Oprah eventually realised the obvious. "We realised, I can't sing," she admitted.

The experiment survived for just one season before quietly disappearing from the show. Ironically, what Oprah considers a career misstep became a memorable moment for fans. She recalled that when Whitney Houston appeared on The Oprah Winfrey Show in 1999 and was asked to sing her favourite song, the legendary singer unexpectedly chose Run On—leaving Oprah both surprised and amused.

The podcast also revealed another lesser-known story behind one of the world's most recognisable names. Oprah shared that she wasn't actually born "Oprah."

Her birth certificate says Orpah, a biblical name from the Book of Ruth. But people kept mispronouncing it. Eventually, "Orpah" became "Oprah." The new name stuck. So did the woman behind it.

Over 25 years after that short-lived musical experiment, Oprah isn't remembered as a singer. She's remembered as one of the greatest storytellers television has ever produced. And perhaps that's why her confession resonates. After building a billion-dollar brand, interviewing world leaders and inspiring generations, the mistake Oprah still laughs about isn't a failed business, a controversial interview or a bad investment. It's a song. One she still insists "was pretty bad."

(With inputs from ANI)