Oprah Tells Keke Palmer Her 1999 Single Is Her Biggest Career Regret: "I Can't Sing"

Oprah Winfrey is known for her wisdom, her influence, and her billion-dollar empire. But even the most successful people have a skeleton in their closet. Or in this case, a song. Oprah sat down with Keke Palmer and revealed that releasing her 1999 single“Run On”is her biggest career regret. She admitted she took singing lessons but ultimately realized her voice wasn’t built for the charts.“We realized I can’t sing,”she said, adding a classic“Girl, please!”for good measure.

The song was originally created as a potential theme for the 13th season of her talk show. It didn’t exactly launch a music career. Oprah has previously called the track“dead to me”in interviews, so this wasn’t a fresh wound. But hearing her own it with such humor and humility is classic Oprah.

She also flipped the conversation to a powerful lesson about ownership. Reflecting on her time filming“The Color Purple,”she explained how giving up a vacation led her to understand the value of owning her work. Her lawyer suggested she own part of her talk show, and that decision paved the way for her incredible success. Have you ever tried something you regretted? How did you bounce back? Let us know in the comments.