What happened with Rosie O’Donnell and Oprah? history explored as comedian criticises TV host for attending Jeff bezos wedding

Rosie O’Donnell has resurrected interest in her complicated relationship with Oprah Winfrey, after she recently added remarks about the media mogul showing up at Jeff Bezos’ lavish wedding to Lauren Sánchez.

In a poem she posted to her Substack, O’Donnell expressed profound discomfort with the “gross excess” of the event, which reportedly cost tens of millions of dollars and was attended by many celebrities, including Oprah.

"Turned my stomach seeing all these billionaires gathering in the gross excess of it all." O’Donnell wrote.

Given their past controversial history, Rosie O’Donald directly criticized Oprah Winfrey for attending the wedding.

"Is Oprah friends with Jeff [Bezos?] Really – how is that possible?. He treats his employees with disdain, by any metric he is not a nice man." O’Donnell added.

O’Donnell’s criticism gained a lot of traction due to the women’s history together. Both were amongst the biggest names in daytime television in the 1990s, Oprah with The Oprah Winfrey Show and Rosie with The Rosie O’Donnell Show. Although they were frequently characterized as rivals in the media, each host appeared on the other’s show to refute that speculation.

Though nothing bad ever happened between them, it is believed that the two stars eventually grew distant from each other due to their career growth and differences. While Oprah Winfrey went on to have a great career, O’Donnell had to deal with major setbacks in the latter part of her career.

In 1996, when Madonna had appeared on the program, Oprah confronted some tabloid headlines that claimed she hated Rosie, claiming that she did not hate or despise O’Donnell and in fact stated that she regularly watched O'Donnell's show.

A look into Rosie O’Donnell and Oprah Winfrey's shared television history and career

The pair's public support for one another increased in 2011, when Oprah Winfrey offered a major career opportunity to Rosie O’Donnell. After wrapping up her eponymous daytime talk show, Oprah launched her own cable network, OWN, and asked O’Donnell to host The Rosie Show.

In interviews, the women gave each other nothing but love for their collaboration. Oprah even flew out to meet O’Donnell in person, before signing her to a deal, apparently to make sure Rosie was in the right mental and professional space for a grand comeback.

"When I heard that Rosie actually might be interested in signing on with me and with OWN, I really couldn’t believe it," she said. "I was like, ‘Really? She would do that?’" Oprah told BC News’ Nightline in 2011.

While that's a pretty good start, The Rosie Show ultimately didn't last long. According to The Things, it went through several major format changes and faced challenges in attracting a consistent audience.

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Executive producer Paige Hurwitz would later speak about the show's cancellation, with one reason being O’Donnell’s high expectations and her aversion to low ratings. Rosie O’Donnell herself said the cancellation was fair, confessing that she had underestimated the challenge of launching a new show on a new network.

Shared public appearances between the two have been scarce ever since. According to critics online, Rosie O’Donnell’s recent comments seem to stem from Oprah being at Jeff Bezos’ wedding, which would indicate that there are some ongoing ideological issues between the two of them.

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