Oprah Admits Her 1999 Single "Run On" Was a Huge Mistake: "I Can't Sing"

Oprah Winfrey is known for her wisdom, her success, and her ability to connect with people. But even she has a few things she’d like to take back. During a recent chat with Keke Palmer on her podcast, Oprah opened up about one of her biggest career regrets: releasing a single in 1999 called“Run On.”She took singing lessons for the track, which was meant to be a theme song for the 13th season of her talk show. But after all that work, she realized the truth. She told Keke,“We realized I can’t sing, even though I took the singing lessons.”She called the song“dead to me”in a previous interview and has never attempted a music career since.

But Oprah being Oprah, she turned the conversation into something bigger. She also shared a story about learning the value of ownership. Early in her career, she was ready to give up a vacation for her role in“The Color Purple.”Her lawyer stepped in and suggested she own a piece of her show instead. That advice changed everything. It set her on a path to owning her talk show, her production company, and her entire media empire. It’s a powerful reminder that sometimes our failures teach us more than our successes.

So what do you think? Is there a career move or a personal project you look back on and wish you could take back? Or do you believe every mistake leads you where you need to be? Share your thoughts with us on social media or give us a call on the show. We want to hear your story.