Not every celebrity had a great time on Rosie O'Donnell's daytime talk show. In 1999, O'Donnell clashed with future Blue Bloods star Tom Selleck on gun laws. O'Donnell recalled the contentious interview as the first time she "challenged" a celebrity who visited her show. At the time Selleck visited The Rosie O'Donnell Show, he had recently starred on a short-lived CBS sitcom called The Closer and in the movie The Love Letter.
"I think it's just the first time that I ever challenged a celebrity," O'Donnell told PEOPLE this week. "Every other one I was nice to. If they said, 'Please, let's not talk about my divorce or my recent drug addiction, drug rehab,' I would do what they asked."
O'Donnell noted that she was never a "get you" interviewer, adding that she did not have an interest in making a guest feel uncomfortable. "Like Johnny Carson taught us, if there was egg on anyone's face, it's supposed to be on the host, not the guest. So I think no one was expecting that I would challenge someone in the way that I did," she said.
During Selleck's stop on Rosie, O'Donnell brought up Selleck's support for the National Rifle Association. Selleck was frustrated, since he was brought on the show to discuss The Love Letter, but O'Donnell continued asking him about the NRA. She insisted he was a spokesman for the controversial lobbying group, but at one point, he called it "absurd."
In the years since the on-air confrontation, O'Donnell has admitted to wishing she did things differently. "In hindsight, if I had to redo [it], I would do it differently," O'Donnell said in 2011, going on to call Selleck a "kind man, who, for the rest of his life, has to be associated with me and that one event." O'Donnell told reporters she was "not really in my best place emotionally," noting that the interview was taped the week after the Columbine shooting.
"I was pretty raw," O'Donnell told reporters in 2011. "It was the first time I was in what I perceived to be a position of power — which I thought came with fame. And I was really disillusioned to find out that it didn't."
In 2007, when O'Donnell was making headlines during her time on The View, Selleck told Access Hollywood he didn't have any ill will toward O'Donnell. "It's hard to pick a horse in that particular fight – not that I'm calling Donald [Trump] or Rosie the horse. I'm not starting anything," Selleck said at the time. "I still like Rosie. I think she needs to take a deep breath and stop thinking everybody who disagrees with her is evil."