O’Brien recently invited Penn on his podcast, Conan O’Brien Needs a Friend. During the podcast, the two chatted about cancel culture and how some tend to write off individuals based on their previous comments and actions.
“I’ve always described myself, I think I’m a 52 percent optimist,” O’Brien explained. “I do believe that everything that’s happened in the last year is going to inform us in the best way and is going to have a very valuable impact on the arts and is going to make things better and more inclusive. I believe in all that.”
He continued: “This whole concept of cancel culture is, ‘we’ve found that someone did something in 1979 that is now not appropriate, they’re dead to us.'”
“It’s ludicrous,” Penn added. The actor then referenced the 27-year-old reporter, who was fired from Teen Vogue in March over past tweets. At the time, many thought the tweets were culturally insensitive to the Asian community.
Sean Penn & Conan O’Brien Openly Discuss Hollywood’s Woes In New Podcast
“When we’re destroying careers like that, what are we really achieving? Or you look at politicians. I give a big nod to anyone that’s willing to enter the public arena who is doing so because they give a damn,” Penn noted.
The pair’s conversation began with the two discussing Penn’s performance in the film Milk. In the movie, he portrayed politician and gay rights activist, Harvey Milk.
O’Brien praised his performance, noting that it helped him connect to the story of Harvey Milk.
“It brings up an interesting point,” Penn said. “Another one I think a lot about these days. Today, almost certainly, I would not be permitted to be cast in that role. We’re living in a time when, if you’re playing a gay lead character, you’d have to be a gay man, or a trans character. And there have been these casting issues.”
He added: “When you have a period of evolution, that certainly has an opportunity for people who have had less opportunities to move forward. That has to be supported. Yet in this pendulum swing society that we’re in, you wonder at some point if only Danish Princes can play Hamlet. It is, I believe, too restrictive. People are looking for gotcha moments and to criticize.”
O’Brien also noted that he feels “uncomfortable” about how people try to put celebrities into boxes and attempt to convince them to have certain viewpoints.
Both icons agreed that their role in the cancel culture conversation right now is to listen. They also added that they hope that the pendulum swings back to a different Hollywood.