What has Rosie O’Donnell been up to? From her surprise friendship with Michael D. Cohen, and her ongoing feud with Donald Trump amid his trial, to a Sex and the City appearance and new TikTok-based show

May 24 , 2024

Rosie O’Donnell attends the opening night performance of A Transparent Musical in California, in May 2023. Photo: Getty Images

Over a career that’s spanned more than 30 years, Rosie O’Donnell made the world laugh and cry as one of Hollywood’s go-to comedians and actresses. She was perhaps best known for appearances in TV shows and films like A League of Their Own, The Flintstones and Web Therapy.

More recently though, O’Donnell has gained a reputation for her off-screen comments that have stirred feuds and controversy, than for her accolades. In particular, her bitter relationship with former US president Donald Trump – that stretches back several decades – continues to make headlines. As the world watches Trump’s hush-money trial play out in New York, O’Donnell has once again become an outspoken critic of the politician – and a surprising supporter of his former fixer, Michael D. Cohen.

Here’s how O’Donnell’s links to Trump are keeping her in the news.

How did Rosie O’Donnell strike up a friendship with Donald Trump’s former fixer, Michael D. Cohen?

O’Donnell, 62, has made headlines in recent weeks because of her surprise friendship with Cohen, the man once known as the former president’s fixer. Cohen first started working with Trump as a special counsel in 2007, and continued to do so for more than a decade, per the BBC. It was also Cohen, according to The New York Times, who once helped Trump carry out his attacks against O’Donnell during their feud.

But when Cohen took to the stand in a Manhattan courtroom earlier this month to testify against Trump in the former president’s hush-money trial, it was a message from O’Donnell that offered support, reports the same source. “Breathe – relax – tell the truth – you got this – I love you,” read the message.

Per the publication, O’Donnell wrote to Cohen after he was jailed for tax evasion and campaign finance violations, saying she forgave him for his part in Trump’s vicious campaigns against her. It was this letter that began a strong friendship between the pair.

What started the feud between Rosie O’Donnell and Donald Trump?

Rosie O’Donnell (left) and Oprah Winfrey speak to the media to promote O’Donnell’s Oprah Winfrey Network (OWN) show, The Rosie Show. Photo: AP Photo

The long-standing war between Trump and O’Donnell is certainly no secret. Both have been outspoken about their dislike of each other. But just how did it all start? As reported by The New York Times, O’Donnell’s initial dislike of the former president began in 1991 while she was filming A League of Their Own with Madonna. According to the publication, during filming, reports emerged that the singer had been on a date with Trump. However, she told O’Donnell that the reports were false and that “Mr Trump had simply made up the story for publicity.”

Former president Donald Trump arrives at the Manhattan criminal court in New York for his hush-money trial earlier this month. Photo: AP Photo

The feud properly ignited during a to-do in 2006 involving then Miss USA Tara Conner, who was caught doing cocaine in a club. Trump, who owned the pageant at the time, said she’d be forgiven if she went to rehab. O’Donnell, on chat show The View, said he was capitalising on the scandal and poked fun at his ability as a businessman. Trump responded by hurling insults at O’Donnell, ridiculing her weight and looks, and calling her “wacko”. O’Donnell left The View a year later, despite high ratings. It was rumoured at the time that the discord with Trump influenced her departure.

Most recently, according to Entertainment Weekly, O’Donnell made a US$10,000 bet with controversial broadcaster Bill O’Reilly that Trump would be found guilty in court. “He’s a cruel, criminal and mentally unstable man. I think he’s the worst thing that ever happened to the United States. His cruelty knows no bounds. When he’s upset and humiliated and embarrassed, he has no control and he goes apes***,” she told former CNN journalist Chris Cuomo on his new show, NewsNation.

Is Rosie O’Donnell returning to TV?

Rosie O’Donnell posted this photo to Instagram earlier this month. Photo: @rosie/Instagram

O’Donnell will be making her TV return on the Sex and the City spin-off, And Just Like That. She’ll be playing a character called Mary on an episode called Outlook Good, according to Variety.

Despite having been a mainstay of daytime TV as part of The View panel from 2006-07 and again from 2014-15, it was her work on her syndicated talk/variety series The Rosie O’Donnell Show and Sirius/XM show Rosie Radio that won her more recognition.

In an interview with Vanity Fair, O’Donnell’s spoke about getting more work at age 60. “There aren’t a lot of women who haven’t had surgery who look kind of real. You find some 60-year-old actresses have so much work done that they don’t even look like real people when you see them in a movie, right? So I always thought that that would be a benefit and that I would work a lot, and it’s been coming true in the last couple years.”

What other projects does Rosie O’Donnell want to do?

Rosie O’Donnell shows off short hair while relaxing at home in this Instagram post. Photo: @rosie/Instagram

In the same interview with Vanity Fair, O’Donnell spoke about how she bought the rights to a woman’s life story after she saw her on TikTok speaking about how she was charged with embezzlement in her 20s. O’Donnell explained how the woman got a 20-year sentence and, after serving 10 years, made TikTok videos about what it was like to be in jail. O’Donnell said she wanted to “take this time to really work on making a show”.

Fame and celebrity

Comedian and actress Rosie O’Donnell, 62, shot to fame in films like A League of Their Own and The Flintstones, but it was her time as a host on chat show The View that made her a household name
These days, she’s better known for her bitter feud with ex president Trump and recently made headlines for supporting his former fixer – but she plans to flex her acting chops again in new gigs