My Interview With an ACTUAL Friend of the Devil

Tucker Carlson is a hate-spewing dumpster fire. But for ten minutes in 2018, I bonded with a man I despise over a long-disbanded jam band.

Let’s get one thing clear right up front. I think Tucker Carlson is a racist asshole.

But also, I’m a freelance journalist. And in 2018, Playboy hired me to interview Carlson. The magazine’s big interview, the one that featured real icons like John Lennon, Miles Davis, Malcolm X, Stephen Hawking, Bob Dylan, Kurt Vonnegut, and the Rev. Martin Luther King Jr. As a longtime contributor, I’d done numerous Playboy interviews, with celebrities I actually admire like Stephen Colbert, Tina Fey, and Steve Carell. But I was reluctant to take on this assignment, if only because of how much I loathed (and still loathe) Carlson.

I said yes anyway. Because I’m a freelance journalist, and therefore a whore.

My editor—not Stephen Randall, my longtime and much-beloved editor at Playboy who got pushed out in 2015 as the magazine’s first death knell (that’s a story for another day), but some other dude—didn’t want the Carlson interview to be a confrontation. He wanted me to find the man behind the divisive Fox News personality. So instead of cornering Carlson with questions like, “Why are you such a racist asshole?” and “You know that every thought that comes out of your mouth is hateful diarrhea that poisons the planet and makes everyone dumber?”, I was tasked with talking to him like a person.