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Rosie O’Donnell to guest host ‘Jimmy Kimmel Live’ during Kimmel’s break
‘The Big Weekend Show’ co-hosts discuss Rosie O’Donnell set to guest host ‘Jimmy Kimmel Live’ during late-night comedian Jimmy Kimmel’s two-month vacation
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Rosie O’Donnell recalls a specific point in her career when she recognized she had accumulated more wealth than she had ever considered possible
The comedian, 64, revealed she chose to walk away from her wildly successful daytime talk show, “The Rosie O’Donnell Show,” after learning she had earned roughly $100 million, saying no paycheck was worth missing time with her children
“When I heard that [number], I thought, ‘OK, now I’m done,'” O’Donnell told Page Six. “And everyone was like, ‘Why are you leaving?'”
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O’Donnell said reaching that financial milestone made her reevaluate her priorities
“I had enough money to take care of everyone in my life, philanthropy and strangers,” she said. “I wanted to be at their softball games. I wanted to be at school plays.”
O’Donnell hosted “The Rosie O’Donnell Show” from 1996 until 2002, when it ranked among the most popular daytime talk shows on television
O’Donnell claimed Warner Bros. attempted to keep the show alive by offering her another $100 million to remain on the air for two additional years
However, she turned it down
“They were like, ‘Why would you say no?'” O’Donnell remembered. “And I was like, ‘Because I already have that money and if I think I need more, something‘s wrong with me.'”
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The actress added that she has never understood those whose wealth becomes their primary motivation
“I don’t get the billionaires,” she said. “I don’t get how people only measure their life in money, not what they can do for other people.”
While O’Donnell has long maintained that leaving television allowed her to be a more present mother, she has also been candid about the heartbreak that came with raising her family — particularly her daughter Chelsea’s years-long battle with addiction and legal woes
The actress recently reflected on an emotional reunion with Chelsea — who is currently serving time in prison — describing the visit as a breakthrough in their fractured relationship
Rosie O’Donnell asked for prayers after her daughter, Chelsea, was sentenced to prison for violating her probation.(Oconto County Sheriff’s Office; Stefanie Keenan/ for ELLE)
“It was the first conversation I’ve had with her in 10 years that lasted more than 25 minutes,” O’Donnell told Page Six
“The first time that I saw her in a consistent way was the four hours in the prison,” she continued, explaining that Chelsea became teary-eyed after a tornado warning forced the visit to end early
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“And that’s the first time I’ve seen, kind of, an empathetic emotion from her,” O’Donnell said. “So, you know, she’s growing up, and I hope that her future is brighter than this past decade has been.”
Following the visit, O’Donnell penned a poem chronicling the experience
“The guard explained the rules,” she wrote. “A hug hello and goodbye only / No money exchanged / Hands above the table / No loud voices.”
Elsewhere in the poem, O’Donnell said her heart “skip[ped] a beat” when she saw Chelsea, writing that her daughter looked “good” and carried a “healthy calm.”
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Rosie O’Donnell chose family over fortune at the height of her success. (Dave Benett/
O’Donnell has publicly supported Chelsea throughout her legal troubles and addiction struggles
Last October, the actress shared a childhood photo of Chelsea on Instagram and asked fans for prayers after her daughter was sentenced to prison following the revocation of her probation
“My child chelsea belle — before addiction took over her life — i loved her then i love her now as she faces a scary future — prayers welcomed,” O’Donnell wrote
Just days earlier, Chelsea had her probation revoked and was sentenced to prison, according to court documents previously reviewed by Fox News Digital
O’Donnell has been open about her fractured relationship with daughter Chelsea. (TheStewartofNY/FilmMagic)
At the time, O’Donnell told Fox News Digital that while the family’s journey had been painful, they remained committed to supporting Chelsea
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“I have compassion for those struggling with addiction — chelsea was born into addiction and it has been a painful journey for her and her four young children,” she said in a statement. “We continue to love and support her through these horrible times. Prayers welcomed.”
Chelsea’s legal issues began escalating in 2024, when authorities charged her with two felony counts of methamphetamine possession, one felony count of possession of narcotic drugs, two counts of illegally obtaining prescription medication and resisting or obstructing an officer, according to court records previously reviewed by Fox News Digital
Following a subsequent arrest, O’Donnell addressed the situation on social media, expressing hope that her daughter would receive treatment
“So yes this is true — after being bailed out by her birth mother — chelsea was arrested again — and is facing many charges related to her drug addiction,” O’Donnell wrote. “We all hope she is able to get the help she needs to turn her life around.”
