Dear Gossips,

It has been a WEEK, which I feel like I say every week, because all the weeks are a WEEK, and have been for like, the last six years, at least. But this week was a tough one, which is why I lit up like a firework when the new episode of Conan O’Brien Needs a Friend dropped and it featured none other than one of my last remaining forever loves, Timothy Olyphant.

I enjoy Conan’s podcast for the rapport he has with his sidekicks, producer Matt Gourley and his assistant, Sona Movsesian, and the long-running comedy bits they indulge in, but also because Conan is a genuinely great interviewer, and the long-form podcast format suits his freewheeling conversation style. But Conan is NEVER better than when interviewing Timothy Olyphant.

Some of it is Olyphant’s incredible charm—he’s good on every talk show—but it’s mostly that Conan and Olyphant are actually friends in real life, something they bring to their conversations. They give each other sh-t, they have in jokes, they are not taking the entire proceeding seriously, they’re just having fun. There are a handful of people who obviously delight Conan, usually fellow comedians, people he clearly admires and understands in a way he doesn’t necessarily get all the actors and pop stars stopping by his show. Timothy Olyphant is the exception, an actor who pokes the same part of Conan as his comedy friends (though it is notable that Olyphant tried comedy for a hot minute in the 1990s, he’s got an instinct for it, even if he’s too handsome for standup).

Anyway, their conversation this week was a DELIGHT. It’s also one that sent me straight to the Youtube channel for the videos, because listening to Conan and Olyphant banter is only half the fun, the other half is watching.

Am I obsessed with how Olyphant has turned into a total silver fox? Yes, of course. But I also enjoy the looseness of it, which again, comes from years of real-life friendship, but also, both of these men have hit the point in their careers where they don’t care about the hustle anymore. Conan is too much of a performer to ever really stop performing—he made a whole documentary about how he can’t stop—but with Olyphant, you can see his guard drop a little. It’s about as relaxed as Conan O’Brien gets in the public eye. It’s a fun conversation, as it always is with these two, and I have been parceling out the video clips all week, as a little treat, and so should you.

Live long and gossip,

Sarah

Timothy Olyphant Gossip

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