A History of Rosie O'Donnell's Complicated Ups & Downs

After working the comedy club circuit and appearing on a handful of TV shows, a 30-year-old Rosie O’Donnell makes her feature film debut in 1992’s beloved A League of Their Own, alongside Tom Hanks, Geena Davis and Madonna. Her work in the role of Doris Murphy earns her a 1993 MTV Movie Award for best breakthrough performance.

O’Donnell’s rising fame earns her an eponymous daytime talk show, which hits the airwaves in 1996 (and runs successfully through 2002). She wins Daytime Emmy Awards for the celeb-heavy series six years in a row — plus a Primetime Emmy Award for her Tonys hosting gig in 1999.

In 1995, O’Donnell adopts son Parker, then an infant. Nine years later, in 2004, she marries Kelli Carpenter in San Francisco, just weeks after the California city begins granting same-sex marriages. In their years together, they go on to adopt daughter Chelsea and son Blake, and Carpenter adopts Parker as her own before welcoming daughter Vivienne (pictured) via artificial insemination. Though couple splits in 2007, though doesn’t announce the news until 2009. “What makes a family is love, and we all love each other,” she tells reporters at a January 2010 red carpet event. “We’re gonna stay together and take care of each other as a family unit.”

Known for voicing her opinion via her own blog and social media, O’Donnell makes an exciting, if not controversial, addition to The View‘s 10th season in 2006. She joins Barbara Walters, Joy Behar and Elisabeth Hasselbeck at the table, but leaves in the spring of 2007 after what ABC says are failed contract negotiations (though some speculate are differences with Hasselbeck).

During her time on The View, O’Donnell becomes increasingly outspoken about Donald Trump, particularly following the controversy over his decision to reinstate Miss USA Tara Conner following her drug abuse scandal during her reign. Trump fires back, even threatening to sue O’Donnell and attempting to pit View co-host Walters against her. “Rosie’s a loser. A real loser,” Trump tells PEOPLE. “I look forward to taking lots of money from my nice fat little Rosie.”

In the fall of 2011, O’Donnell moves to Chicago and launches a new series, The Rosie Show, on Oprah Winfrey’s OWN network. That December she announces more happy news: she’s engaged to girlfriend Michelle Rounds. Two rounds of bad news follow, though — O’Donnell’s show is canceled in March 2012 and Rounds is diagnosed with a rare disease called desmoid tumors around that time — so the couple quietly moves up their nuptials, saying “I do” in June and announcing the news in August.

Newlywed bliss doesn’t last long, though, when O’Donnell suffers a heart attack that August. A week later, she takes to her blog to thank fans for being there.

“When we r both well enough will have the wedding of r dreams surrounded by those we cherish,” she writes. “Thankful for the love and support so many have given us during these trying times.”

She’s back! As several View hosts depart, O’Donnell joins Whoopi Goldberg at the table for 2014’s season 18, with Rosie Perez and Nicolle Wallace rounding out the cast. But again, her stint is short, and she leaves six months later for personal reasons. “I think Rosie and Whoopi together was not peaches and cream,” Barbara Walters says. “And I don’t think we needed the two of them together.”

Around that time, O’Donnell also announces she’s filed for divorce from Rounds on the grounds of “an irretrievably broken relationship.” They’d separated the November prior, sharing custody of Dakota, the 2-year-old daughter they adopted together.

However, Rounds files for sole custody of the child, to which O’Donnell tells PEOPLE, “This is an absurd and desperate attempt to use a child for her own gain.” A lawyer for Rounds tells Page Six the attempt to gain full custody “is unequivocally in their child’s best interest and general welfare.” O’Donnell eventually wins full custody of their child.

In August 2015, O’Donnell asks fans to help find her daughter Chelsea, who goes missing weeks before her 18th birthday. In addition to her plea, her rep tells PEOPLE, “Chelsea, like millions of people, lives with mental illness. It has been a difficult road for Chelsea and her family and they just want her back safe. Rosie and Chelsea] have a good relationship. Rosie loves Chelsea very much.”

The teen — who disappeared with her therapy dog, Bear, and went off her medication before leaving home — is found safe one week after disappearing, though in the New Jersey home of an alleged heroin addict who’d reached out to her online.

O’Donnell’s rep confirms that following her 18th birthday, the teen moved to Wisconsin to live with her birth mother. She also claims O’Donnell kicked her out of the house, and says though she suffers from depression and anxiety, she is not mentally ill.

In happier news, O’Donnell shows off a 64-lb. slim-down in 2015. She reveals she had a vertical gastric sleeve surgery in 2013, which “changed my life,” she tells PEOPLE. “It doesn’t reroute your intestines. You have no issues with going to the bathroom in public. But your relationship with food ends. I don’t feel the same pull for it. I feel so much freer now in terms of needing to move and play with my kids.”

In 2016, O’Donnell and Chelsea reunite in a smiling selfie the star shares on Twitter. “chelsea and me – what a difference a year makes #hopelives,” she writes.

In March 2017, however, Chelsea appears on Inside Edition to talk about her secret 2016 wedding to plumber Nicholas Alliegro, whom she marries after just three months. “She was upset that we got married without telling her, which I totally understand,” Allegro says.

Chelsea says the tension goes beyond that. “The last time we got into an argument, we ended up screaming at each other and I left the room,” she shares. “Growing up, I never really got along with her and then once she kicked me out, I was just kind of done.

“I would just want her to know that we’re doing really great and we’re happy,” she says, and adds that she’d “someday” like to make peace with her mother: “I hope.”

During a May appearance at the GLAAD Media Awards in N.Y.C., O’Donnell says, “Things have been rough in my family.”

That September, Chelsea announces she’s pregnant — but makes it clear her estranged mother won’t be a part of the baby’s life. 

On Sept. 15, 2017, news breaks that O’Donnell’s ex, Rounds, 46, is dead of an apparent suicide.

“I am saddened to hear about this terrible tragedy. Mental illness is a very serious issue affecting many families. My thoughts and prayers go out to Michelle’s family, her wife and their child,” O’Donnell tells PEOPLE in a statement.