Rosie O’Donnell Reflects on Her Heated 1999 Debate With Tom Selleck: ‘He Wasn’t Prepared’

Rosie O’Donnell looked back at one of the most controversial and heated conversations on her former talk show, where she grilled actor Tom Selleck on his ties to the National Rifle Association (NRA).

O’Donnell appeared on the Thursday, June 18 episode of Watch What Happens Live, where host Andy Cohen asked her if she regrets the now-infamous encounter from 1999, when the Magnum, P.I. alum appeared on The Rosie O’Donnell Show to promote his movie, The Love Letter, and ended up having to answer for his involvement in an NRA ad following the shooting at Columbine.

“Well, I think he wasn’t prepared and nor was the audience because I had never done anything like that on the show, but I was so undone by Columbine,” she explained. “I couldn’t believe he put an ad in a magazine that said, ‘I am the NRA.’ If you’re going to say ‘I am the NRA,’ you need to answer for the NRA and he didn’t seem to want to.”

“I do feel bad now that he’s older and I am too and, you know, I don’t want it to be something that he remembers so horrifically, but I think that it wasn’t a good time for him,” she added.

During the heated exchange back in 1999, the comedian took Selleck to task on the organization’s objections to gun control regulations.

The actor looked visibly uncomfortable and tried to explain that he’s not a spokesperson for the NRA and can’t speak to their position on certain issues and argued, “now you’re questioning my humanity.”

In 2007, the Blue Bloods alum told Today that he doesn’t have any hard feelings with O’Donnell about the incident, but stated: “I still like Rosie. I think she needs to take a deep breath and stop thinking everybody who disagrees with her is evil.”