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Rosie O’Donnell is one of the most famous people in the world. She was funny, opinionated, relatable, and unafraid to put herself out there in the name of entertainment. O’Donnell entered the nineties as an up-and-coming screen star and comedian, and in early 1999, she aimed to leave them as a television power player. However, when the world changed on April 20, 1999, so did O’Donnell’s relationship with her anxiety medication. 

Rosie O’Donnell’s brush with fame

Rosie O'Donnell
Rosie O’Donnell | Shannon Finney/Getty Images

IMDb notes how O’Donnell was always lauded for her acting ability and comedic chops, but her greatest claim to fame was her media-friendly personality. Always quick with a joke, a jab, or a witticism, O’Donnell became a favorite on talk shows around the world at the same time she appeared in films like Sleepless in Seattle, The Flintstones, and several other hits.

While she never truly became Hollywood A-List material, Rosie O’Donnell’s success on the big and small screens made her a perfect talk show host. In 1996, she fulfilled that dream and became one of the biggest names in entertainment. Then, in 1999, everything changed both on a global scale and in the performer’s tumultuous personal life. 

The world changes with us

Speaking with Danny Pellegrino on the Everything Iconic podcast, O’Donnell harkened back to the height of her fame when her talk show made her bigger on the small screen than she ever was on the big screen. According to O’Donnell, the fame started making her feel like she could help the world with money and voice. When the Columbine shootings occurred in 1999, however, it marked a change in how she viewed not only her fame but society as a whole. 

“There were so many changes in my life so quickly. The show started in ’96, and three years later was Columbine. And I don’t know. I thought I couldn’t believe that I lived in a country where children were being murdered in their school. And it didn’t seem possible to me. Of course, since then, there’s been thousands and thousands of mass school shootings.”

O’Donnell realized that despite her rising star in entertainment, the world around her was still a broken mess. This caused an anxiety spiral that led her to take medication that she credits with keeping her afloat while life around her spiraled out of control. 

“Since then, I’ve been on medications, since ’99, April ’99, with Columbine. And I only went off once in the time since then,” she told the podcast. 

O’Donnell never quite experienced the same level of fame after her talk show, but it’s not entirely out of her hands either. She went on to speak about how her early friendships shaped her relationship with the fame monster. 

Rosie O’Donnell: conquering fame 

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One of Rosie O’Donnell’s earliest and most iconic roles was as a female baseball player in the Tom Hanks, Geena Davis, and Madonna comedy, A League of Their Own. While the film was a massive hit that still packs a punch today, her relationship with her castmates, namely Madonna, showed the downside of being famous.

“Madonna couldn’t go anywhere. Now, mind you, that’s The Beatles or Elvis kind of fame. That’s not my kind of fame, but that once-a-generation kind of fame is really a tidal wave. And you try to just keep your head above the surface and not drown,” O’Donnell said. 

O’Donnell’s career has been a roller-coaster affair. At one point, she was America’s favorite daytime talk show host. After coming out of the closet, a pair of stints on The View, and several run-ins with former President Donald Trump, made her notable for several reasons. Despite the tumult, O’Donnell has no regrets.

Rosie O’Donnell is now medicated, opinionated, and outspoken about her troubles and the troubles of those around her. This is what has kept her relevant years after any high-profile work. Now twenty years removed from her hit show, O’Donnell is just happy to have her wits despite her early brush with fame.