Oprah Winfrey Names the Career Mistake She Deeply Regrets

Oprah Winfrey recently reflected on one of her biggest regrets throughout her storied career.

The television host and media icon spoke about her brief stint as a singer during an episode of the Baby, This is Keke Palmerpodcast published July 21. 

KekePalmer playfully sang the lyric “I think I’m gonna run on” from the Black spiritual song “Run On,” which Winfrey recorded as her first and final single. The track became the theme song for the 13th season of The Oprah Winfrey Show in 1998. 

“Girl, please,” the 72-year-old told a giggling Palmer. “That is one of the mistakes of my career.”

The One of Them Days actress said her recording was “no mistake,” but Winfrey did not agree. 

“It is a mistake,” the talk show host doubled down. “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, ‘There’s this song. It’s an old spiritual.’”

Winfrey’s talk show aired for 30 seasons from 1986 to 2011, winning 47 Daytime Emmy Awards throughout the decades. 

The media mogul sang the lyric “I think I’m gonna run on” for Palmer. The podcast host responded, “You got to give them a little slave hymn sometimes.” 

Winfrey revealed she wasn’t surprised her rendition of “Run On” never took off. It was only used in one season of her show.  

“We realized, I can’t sing,” she explained, “even though I took the singing lessons.”

She added that the song was produced using a church choir for backup vocals to improve it, but  “it didn’t work.”

The 32-year-old actress told Winfrey that her singing “wasn’t bad,” but the former talk show host resisted her compliment. 

“You know it was bad,” she said. “You’re just saying that ’cause you’re looking at me. It was pretty bad.”