Oprah Winfrey worked her way to becoming one of the most powerful women in the world. From her early days on television to having her own talk show to leading her own network, Winfrey is an inspiration. Her journey has taken her to the very top, and it seems like she is more than happy to stay there.
Another beloved talk show host is David Letterman. The witty host made himself a staple in the homes of late night viewers for decades. He has interviewed countless celebrities over the years. Letterman’s show became the place for a famous face to promote their latest project.
However, as successful as these two forces were, they didn’t always get along. Despite Winfrey’s enormous power, she felt so defeated and uncomfortable during her first appearance on Letterman’s show that she didn’t return for 16 years.
When she finally made her return, she confronted Letterman about their rivalry. The two eventually put the past behind them and laid it all out during a revealing, heart-to-heart interview.
Oprah Refused To Appear On Letterman’s Show For 16 Years After Her Disastrous First Appearance
For many years, rumors circulated of a feud between Letterman and Winfrey. According to reports, the bad blood began when Winfrey was a guest on Letterman’s show back in 1989. Winfrey was rumored to be “uncomfortable” by the experience and refused to be a guest on his show again.
When interviewing Letterman for an episode of Oprah’s Next Chapter in 2013, Winfrey confirmed the story.
“You had asked me before to do [your show] in Chicago… and it was a terrible experience for me,”
Winfrey told Letterman
. “The guy in the audience started yelling, ‘Get her, Dave!’ You were sort of baiting the audience, and there were a bunch of drunk guys down the front. I was trying to like, you know, mitigate the whole thing, and it felt so uncomfortable to me. I didn’t want to have that experience again.”
In the years that followed, Letterman joked about Winfrey frequently, including at the 1995 Academy Awards. Ten years later, Winfrey appeared as a guest on Letterman’s show again.
“Could you tell me please what has transpired?” Winfrey asked Letterman. “I have never for a moment had a feud with you.”
Despite the appearance being promoted as a reconciliation of sorts, it actually amounted to nothing more than the two questioning how the feud began.
In 2010, Letterman told Jon Stewart that Winfrey was mad at him when he stuck her with his restaurant bill when they were vacationing at the same place.
“This predates the Academy Awards. She hated me long before then,”
Letterman said
. “She was with Steadman, I was with my then-girlfriend Regina. We were both at a restaurant having lunch on vacation. I said to Regina, ‘Oh, this is hilarious, I’m gonna make Oprah buy us lunch.'”
When the waiter arrived at Letterman’s table to give him the check, Letterman said, “Oh, this woman right over there has been kind enough to take care of our check.”
According to Letterman, he waved to Winfrey as he and Regina left the restaurant.
“We got a free lunch and that’s where it started,” Letterman said.
When speaking to Winfrey during their 2013 interview, Letterman apologized for her bad experience on his show. He said that he would be “embarrassed” to see the tape of the interview now.
David Letterman Also Got On The Bad Side Of Another Powerful Woman In The Entertainment Business
Winfrey wasn’t the first powerful woman who got upset by Letterman’s actions.
In 1994, Madonna appeared on the Late Show with David Letterman. Her appearance marked her second time speaking to Letterman, but her first appearance by herself. She previously appeared with comedian Sandra Bernhard in 1988.
Madonna called out Letterman for his constant jokes at her expense on his show. She also dropped the “f” bomb a whopping 13 times.
Madonna also made various innuendos. To top it all off, Madonna protested every time Letterman tried to go into a commercial. There were even audience members who booed her and yelled at her to get off the stage.
Her appearance caused a wave of backlash in the press.In an interview with Rosie O’Donnell, the comedian said that she was told by Madonna that the producers encouraged her to swear during the interview. Madonna herself said in an MTV interview that it was “a performance” and said the exchange “wasn’t a real argument.”
The appearance came off the heels of the backlash Madonna was receiving as a result of her 1992 “Sex” book.
Madonna later said that her appearance was the result of her anger over how the public was treating her at the time.She also told Howard Stern in 2015 that she was dating Tupac Shakur at the time, who got her “all riled up about life in general.”
Madonna and Letterman’s first public appearance together since the infamous interview took place at the 1994 MTV Video Music Awards. The talk show host accompanied the singer on stage to present an award. During the moment, Letterman joked about her recent appearance on his show.
“I’ll be in the car,” he said. “Watch your language.”
In 1995, Madonna made a brief appearance, giving Letterman flowers for Valentine’s Day.
“I’m a changed woman since I met you,” Madonna said. “I’m not gonna say f*** anymore!”
Her first full interview with Letterman since the 1994 appearance came in 2000.Madonna was promoting her album “Music” and spoke to Letterman about the controversy. She was also a guest in 2003 when promoting her children’s book, “Mr. Peabody’s Apples.”
Madonna appeared on the show again in 2005 when promoting her “Confessions on a Dance Floor” album. At the time, the singer suffered several broken bones after falling from a horse. Letterman and Madonna both concluded the interview by riding on two horses through the streets of New York City.
- In 2007, Madonna once again appeared on Letterman following the adoption of her son David. Letterman defended Madonna against the brutal criticism she received from the media about her adoption.
- Her final Letterman appearance came in 2009, when promoting her greatest hits album “Celebration.”
- Madonna’s most recent exchange with Letterman came in 2021, when doing a Q&A to promote her “Madame X” concert film. Letterman asked Madonna if she missed him, to which she said yes.
David Letterman Opened Up To Oprah About Another Feud He Was Involved With
While speaking to Winfrey on Oprah’s Next Chapter in 2013, Letterman addressed his feud with Leno.
“Jay and I were friends — we were always friends, before all of this happened,” Letterman said, referring to the moment Leno took over Johnny Carson’s spot.
Letterman also revealed that those involved with The Tonight Show approached him to take over. Letterman asked them if Carson approved of the idea, but was told Carson didn’t know about their asking him. Letterman told them that he wouldn’t take the job unless Carson approved.
According to Letterman, Leno was announced as Carson’s replacement shortly after that.
Letterman also told Winfrey about the time he spent with Leno in the early years. He said that whenever a fellow comic bombed, Leno would gather a group of comics to watch their performance and make fun of them. Letterman said that this would make him uncomfortable.
“I’ve never met anyone quite like Jay. And I will say, and I’m happy to say, I think he’s the funniest guy I’ve ever known,” Letterman said.
“Just flat out. If you go and see him do his nightclub act — just the funniest, the smartest, wonderful observationist and very appealing as a comic. Therefore, the fact that he is maybe the most insecure person I have ever known — I could never reconcile that.”
During the 2010 Super Bowl, Leno appeared alongside Letterman and Winfrey in a commercial to promote Letterman’s show. The reunion surprised viewers who weren’t aware the two had reunited.
Leno spoke about the commercial and how he became involved during an episode of The Jay Leno Show.
“I’m sitting in my office and Rob Burnett, Dave’s producer, calls my producer Debbie and says, ‘Hey, Dave has an idea for a Super Bowl commercial,’” Leno said.
He added, “Well, all right, and then he tells me the idea and this is Dave’s idea and I thought, that’s great. ‘Cause you know no matter what animosity there is among comedians a good joke is a good joke.”
According to Leno, the whole thing had to be filmed in secret. Leno flew to New York and wore a disguise while on his way to Letterman’s studio. He claimed that nobody, not even Letterman’s staff, knew about his involvement in the commercial.
“Well, I walk in and I see Dave, he puts his hand out and I shake his hand out and I shake hands and you know whatever happens for the last 18-years disappeared,” Leno said. “It was great to see my old friend again.”
He added, “It was wonderful. He was very gracious. We talked about the old days and we told some jokes and it was really good to see him.”
Leno then said that an NBC executive approached him with news about Letterman when he returned to L.A. The executive told Leno they believed President Obama shot a commercial for Letterman. Leno then said that he played along with the executive and even checked for updates until the Super Bowl.
However, according to Variety, Leno flew the NBC jet to New York to film the commercial. They also reported that NBC’s Jeff Zucker and Jeff Gaspin signed off on the promo.
