Divorce, Drama & More: The Ups & Downs Of Rosie O'Donnell's Life In The Limelight

It can be hard to imagine now, but in the early days of Rosie O'Donnell's career, she had a reputation not as someone who courted controversy, but as someone who could be reliably nice. She later told Ramin Setoodeh in his book "Ladies Who Punch" (via BuzzFeed) that she leaned into it when she sought someone to pick up her hit '90s talk show, explaining, "I was not really known for anything political at the time as much as I was just a truth-telling comic, who was funny and round."

The decades that followed have been quite tumultuous for the "Harriet the Spy" star, finding her frequently battling some high-profile figures in the headlines. Along the way, even as O'Donnell has continued to reinvent herself and find new avenues of success, she's also dealt with a number of significant setbacks in her personal life. Some of them, she's handled with grace; others have gotten her some serious pushback from the public.

She's starred in family-friendly films and participated in some of the wildest feuds between "The View" co-hosts in history. She's made people laugh, and she's made people mad. Above it all, she told Setoodeh, there's one thing she tries to keep consistent: "I don't lie." Read on to learn about the ups and downs of Rosie O'Donnell's life in the limelight.

Rosie O'Donnell had a very difficult childhood. O'Donnell's mother died when she was 10, and O'Donnell was abused by her father. She told Ramin Setoodeh in "Ladies Who Punch" that it was very difficult to handle as a child. "Any child who is put in that position, especially by someone in the family, you feel completely powerless and stuck," she said, "because the person who you would tell is the person doing it."

Thankfully, O'Donnell soon found comedy. There was a learning curve at first; she didn't quite understand that comedy was about developing her own voice. On "The Talk" (via Yahoo!), she confessed that she'd once lifted part of a Jerry Seinfeld routine onstage, only to be called out by the other comedians on the lineup. "They go, 'You have to write your own jokes,'" she recalled. "I'm like, 'Listen, Streisand does not write her own songs.'"

In 1984, having crafted her own act, she appeared on "Star Search," a televised talent show that launched the careers of celebs like Christina Aguilera and the members of Destiny's Child. Though she didn't win, O'Donnell found that the exposure that came from the show finally opened doors. Her stand-up career took off, even though female comedians weren't necessarily given the same opportunities that funny men got. "[T]hey would put up on the marquee 'Female Comic Night!'" O'Donnell reflected to The New Yorker decades later. "It was such a rarity. A lot of times, the club owners used to say to me, 'If you are not good, I'm never booking another woman, because the last two sucked.' It was so misogynistic. It was so unbelievably a male-dominated profession."

In 1992, Rosie O'Donnell got her biggest break yet. She'd spent some time as a V.J. on VH1, but she decided she was ready for an acting career. She won a role as Doris in "A League of Their Own," which was then one of the most sought-after films in Hollywood. In fact, O'Donnell told writer Erin Carson that she viewed the part as a last-ditch attempt to make it in showbiz. "If I don't get this part, I'll quit show business," she remembered thinking. "If there's one thing I can do better than Meryl Streep, it's play baseball."

The film was a massive success, and even though O'Donnell was acting alongside entertainment industry heavyweights like Geena Davis and Madonna, she became one of the film's breakouts. It even happened while they were filming, according to her friend Janette Barber, who noted that Madonna got cheers from the thousands of extras at the start of filming. "By the end of the month, Rosie would walk out and it would be like the second coming of Christ," Barber recalled. "Joan Rivers was like that, too. She would take that extra minute; she would remember them."

O'Donnell is still friends with the pop star, for the record. Bonding over their shared childhood tragedies helped Madonna and O'Donnell become forever friends, and as O'Donnell's post-"League" career took off, Madge stuck with her.

In 1996, Rosie O'Donnell launched "The Rosie O'Donnell Show," a daytime talk show like nothing else on television. While daytime TV was mostly the home of scandalous programming like "The Jerry Springer Show," O'Donnell thought that there might be a market for something a little lighter, a little friendlier. "A lot of Broadway, a lot of singing, and no celebrity gets hurt," she explained to Ramin Setoodeh in "Ladies Who Punch." She added, "It was a celebrity safe zone."

The show was wildly successful, and her fan-first approach to talking to famous people paved the way for later shows hosted by folks like Ellen DeGeneres, Jimmy Fallon, and more. Unfortunately, behind the scenes, the sudden stratospheric success was a lot for her to handle. Producer Daniel Kellison told Setoodeh, "It was a s*** ton of pressure on Rosie at all times. I was in my early 30s and I'm tasked with running this multimillion-dollar corporation."

Ultimately, the friendly facade started to crack in 1999, when O'Donnell interviewed actor Tom Selleck shortly after the Columbine school shooting and asked him about his support for the National Rifle Association. It didn't go well. "There were personal attacks on me and my family," O'Donnell told Setoodeh of the aftermath. "They are a terrifying group, and they know how to shut people up." She fell into a depression, panicked about the idea that she couldn't use her fame to help people in the way she'd always assumed. "I had some sort of break. I couldn't sleep. I couldn't eat. I couldn't stop crying." Her show lasted several more seasons, but a different, more political O'Donnell was coming to the forefront.

During the height of her talk-show success, executives learned that kids loved Rosie O'Donnell. Movies like "Harriet the Spy" and "The Flintstones" proved she could speak to younger audiences, so she leaned in, picking up hosting gigs for various awards shows. She helmed the Tony Awards and the Grammys, but her biggest impact came when she took over the Kids' Choice Awards on Nickelodeon.

In 1997, Newsweek dubbed her "The Queen of Nice," a nickname that might seem ironic to people who grew up watching O'Donnell's later, more outspoken persona quarrel with her co-hosts on "The View." In the '90s, though, it was true. She also partnered with Nickelodeon on an episode of "Nick News," a show that featured kids sitting down with adults and host Linda Ellerbee to discuss important issues. She told Radiance magazine in 1997 that their body image-focused episode seemed to have resonated. "I've always been conscious of not playing into the idea or the thought that we all have to be the same size," she said. "I always think it's a positive thing instead of a negative thing if it makes people feel inspired in some way or at least represented."

In 2001, after several years of handing out awards, O'Donnell made headlines when she took several weeks off from her talk show due to a staph infection. While Nickelodeon planned to replace her and pass her Kids' Choice Awards hosting duties to someone else, O'Donnell insisted on going on. As spokesperson Jennifer Glasek told the New York Daily News, "Rosie really loves that awards show and she really felt as though she'd be letting the kids down if she wasn't there."

Like many New Yorkers, Rosie O'Donnell witnessed the atrocities that took place in New York City on the morning of September 11, 2001. She was at her studio getting ready to film when an assistant turned on the news, and they saw the second plane crash live on television. "I don't know that I'll ever be able to adequately describe what that moment felt like," she said on CNN the following year. "It felt to me as though the entire world shifted, as though my perspective on life and good and evil and Republican and Democrat, everything was shaken up like a snow globe in that moment."

O'Donnell told her staff that anyone who couldn't get out of the city should go to her townhouse. She went to pick up her son from school and then returned home. "There were a hundred people in our townhouse," she told The Associated Press. "[A]s soon as the tower fell, I fell asleep. It was almost like the computer of my brain, and my psyche, and my heart couldn't take it anymore."

Several months later, as the city recovered, O'Donnell took the stage at Caroline's, a legendary NYC comedy venue. Still reeling from the attacks, O'Donnell decided to finally address what she hadn't been allowed to say while promoting her talk show. Appearing on "Red Table Talk: The Estefans" (via ET) years later, she recalled, "I'm like, 'I'm gay. Listen, 9/11 happened, I'm gay. I'm telling you all, I'm gay. In case the buildings blow up again, I'm so, so gay,' you know?"

Rosie O'Donnell's official coming out happened several years after Ellen DeGeneres rocked the entertainment industry with her own. The two had been friends in the comedy scene, and as DeGeneres prepared to have her character come out on her sitcom, the comedian appeared on O'Donnell's talk show to tease the announcement. "I said, 'I got to figure out a way to stand next to her so that everybody in the know is going to know I'm not leaving her out there alone,'" O'Donnell later recalled to Ramin Setoodeh in "Ladies Who Punch." Instead of bantering about DeGeneres being a lesbian, they instead teased a reveal that the character was Lebanese. "Maybe I'm Lebanese?" O'Donnell cracked.

Unfortunately, the two had a falling out after O'Donnell came out, too. DeGeneres appeared on "Larry King Live," and he asked her why O'Donnell's career had fallen apart now that she was out of the closet. "I don't know Rosie," DeGeneres replied. "We're not friends."

O'Donnell took that personally, even printing up T-shirts for her staff with those two sentences. She explained to The Hollywood Reporter why it hurt so much. "I know her mother. I could identify her brother without her in the room. I knew her for so many years," she reminisced. "It just felt like I don't trust this person to be in my world."

Several years after the end of her talk show, Rosie O'Donnell returned to daytime television as one of the panelists on "The View." She quickly became known as something of a firebrand, providing a more liberal counterweight to some of the opinions that got tossed out on that show. After all, while the initial concept of "The View" involved women getting together to talk about issues of the day, plenty of arguments on "The View" went way too far, and O'Donnell participated in a few of them herself.

In 2007, as the Iraq War had dragged on for several years, O'Donnell and co-host Elisabeth Hasselbeck quarreled on air about their opposing viewpoints. The segment was riveting television, and producers put the two on a rarely used split-screen, allowing viewers to see uncut footage of the entire argument.

In "Ladies Who Punch" (via Variety), "The View" stalwart Joy Behar suspected that the segment was so controversial because of O'Donnell's sexuality in contrast with Hasselbeck's conservative image. "There was a little bit of a crush. But not that I wanted to kiss her," O'Donnell confessed in the book. "I wanted to support, raise, elevate her, like she was the freshman star shortstop and I was the captain of the team." O'Donnell initially left "The View" amid the resulting controversy at the end of that season, but she continued to fill in as a recurring host for years afterward.

In the years that followed her sudden departure from "The View," Rosie O'Donnell's personal life was in turmoil, too. She and partner Kelli Carpenter had married in 2004, during a brief window when San Francisco briefly allowed same-sex weddings performed by then-mayor Gavin Newsom. They were mired in legal drama, and their marriage was eventually annulled, but O'Donnell and Carpenter remained together for several years, going their separate ways the same year O'Donnell left "The View."

In 2010, after not appearing in public much, O'Donnell appeared on "The Oprah Winfrey Show" (via After Ellen) to talk about what she'd been up to. Thankfully, because there were several adopted children involved, the two remained close after their breakup. "[T]he emotional connection is really the most intense, and so when [lesbians] break up, I have found they stay connected," O'Donnell explained to Winfrey. "Every woman that I have ever been with, besides one, is still in my life."

After the end of her relationship with Kelli Carpenter, Rosie O'Donnell fell in love with Michelle Rounds. The two married in 2012 and adopted a child together, but by 2014, the relationship had hit the skids. Although she'd returned to co-hosting "The View," O'Donnell clashed with Whoopi Goldberg's on-set behavior, so that year she left her occasional gig co-hosting "The View" entirely. A representative told Us Weekly that her home life was to blame. "Rosie has teens and an infant at home that need her attention," the spokesperson said. "This has been a very stressful situation. She is putting her personal health and family first."

By early 2015, the divorce had been finalized. Yahoo! reported that as the two exited the courthouse together, O'Donnell joked, "There's peace in the Middle East." Unfortunately, while the comedian may have been looking forward to maintaining a friendship with her ex-wife — which she had explained she had with all of her exes in her interview with Oprah Winfrey — Rounds died in 2017.

Rosie O'Donnell has continued to perform and act, including appearing on shows like "Hacks" and the "Sex and the City" revival "And Just Like That..." For the most part, however, she pulled back from public life, instead connecting with fans primarily through social media. She took to platforms like Instagram and TikTok, amassing a following that grew to love her updates about her daily life raising her children, including one who has autism.

In 2025, seeking a quieter life away from the hustle and bustle of life in America, O'Donnell moved her family to Ireland. "I was going to have to be mentally well in order to take care of Clay going through puberty and school, so I had to leave," she told The Irish Times.

O'Donnell remains happy with all of her success. After all, when she stepped away from her talk show, people tried to convince her to stay. Instead, she wanted to raise her kids. "They offered me $100 million to stay for two more seasons and I said no. Because by then I already had $100 million in the bank," she explained to The Irish Times. "If you have $100 million and you're thinking you want more, then you are missing the point of your life."

Rosie O'Donnell has become one of many celebs who have spoken out about using weight-loss drugs. In 2025, she told The Irish Times that she was on Mounjaro for diabetes, initially not expecting just how quickly she'd lost weight. She said it's helped her give up on the shame that can come with being overweight, explaining, "[Y]ou can feel your whole life like it's your fault. And then you get on this medicine and you go, holy crap, there's a plate of chocolate chip cookies and they are no longer calling my name."

In 2026, some American fans got their first glimpse of O'Donnell in several years when she returned from Ireland to attend the Tony Awards. O'Donnell had been open online about having gotten a facelift, and she debuted the refreshed look on the theater award show's red carpet in New York. Speaking with E! News, she explained, "I think all that matters is truth and love, and so I wanted to be truthful and say all the complicated emotions I had about it."

Fans online were stunned, especially as O'Donnell joked that there were paparazzi waiting for her at the airport for the first time in more than a decade as she touched back down in America. One user wrote on X, "that's the best f***ing facelift i've ever seen."