I Want To See Timothy Olyphant Ruin Conan O'Brien's Vacation

I realize that the headline of this newsletter might not, in a vacuum, make a lot of sense. Conan O’Brien is a good man. I do not usually want to see bad things happen to him. Timothy Olyphant is a good man. He looks great in a cowboy hat and excels in roles where he is saving the day as opposed to ruining it. I will have to provide some context here. This is the five-step process I went on to get to a place where I want to see Timothy Olyphant make Conan O’Brien absolutely miserable on a vacation.

STEP ONE: Timothy Olyphant recently appeared on Conan’s podcast, Conan O’Brien Needs A Friend, where he promptly grabbed the wheel and careened the entire production into a fireworks factory... but, like, in a good way. He and Conan actually are friends in real life and he appears to find a heap of glee in needling Conan relentlessly, about everything, just being a charming rascal who zigs when you expect him to zag and zags when you expect him to zig. The episode is a lot of fun, especially if you’re a longtime fan of Conan and his patterns as a host and comedic performer. I linked to it in the newsletter last week but here it is again for reference.

STEP TWO: Olyphant has done this a lot, actually. He’s a frequent guest on this podcast and has done Conan’s various TV shows, too. It’s the same thing every time. He takes over completely and it flummoxes Conan, one of the fastest and brightest comedic minds of our time. Part of this is because their personalities seem so different: Conan, a tightly wound East Coast intellectual with an encyclopedia for a brain; Olyphant, a laid-back California dude with great hair and a smirk. But part of it is because of their similarities. They both thrive in chaos, with Conan whirring himself into a comedic mania and Olyphant just sitting back and giggling as everything burns around them. Two paths to a similar destination. You could, perhaps, if you were me and loved to say things like this, say that the two of them are not so different after all.

STEP THREE: Conan’s travel show, Conan O’Brien Must Go, was picked up for a third season on HBO Max earlier this year.

STEP FOUR: Conan often has guests with him on an episode of that show. Maybe “often” is the wrong word. He sometimes has guests. Javier Bardem was with him in Spain. His most frequent foil, Jordan Schlansky, a longtime producer and a very serious man who contrasts well with Conan’s playful bounciness, joined him in Argentina. Those two are fun together. It’s a blast to see Conan ping-pong off of him and poke holes in his snobby exterior. It’s also true that Jordan, like many of the guests on Conan’s podcast and travel show, tends to defer to Conan when he gets cooking, in part because Conan’s name is in the title of the show and in part because, like, if Steph Curry just made six three-pointers in a row, you keep giving Steph Curry the basketball for a while, you know? I get it. But sometimes it's nice to see roles get reversed, to see the antagonist get antagonized, to see a person who is an improvisational genius get his tongue tied up a little by a devious little scamp.

Which brings me to…

STEP FIVE: I want to see Timothy Olyphant guest-star on an episode of Conan O’Brien Must Go. I don’t care where they end up. The location isn’t important. Just put the two of them on a plane — please also start the episode in the airport so I can see Timothy Olyphant mock Conan’s travel habits, too — and send them wherever you want. Venice would be fine. So would Cairo. Or Rio. Or, like, Pittsburgh. I mean no disrespect to the people of Pittsburgh when I say that (it’s actually a very nice place!), I’m just saying it doesn’t have to be a tropical or far-flung spot. All I’m asking for is one hour of television where Conan O’Brien attempts to enjoy himself in a new and exciting city but is thwarted at every step by a grinning Timothy Olyphant. Maybe Olyphant has a cowboy hat on. Maybe he brings Beyoncé. 

I can be flexible here. But only up to a certain point. Let’s get to work on this one.

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STUFF I CLICKED ON

— Amanda Mull wrote a banger on how weird trends have become in the social media age ($$$)

— Dan McQuade did the deep-dive into the Larry King estate sale I probably should’ve done myself (gift link)

— Jacob Oller took a blowtorch to Ice Cube’s new War the Worlds remake and/or commercial for Amazon Prime

— say what you will about South Park, there’s something kind of commendable about using your success to become ungovernable ($$$)

— Bill Hader has a good Michael Bay story

— important question: “Wait, Just How Many Movies and Series Named Good Boy Are There?”

— ITYSL season four question mark

— Naked Gun sequel question mark

— Molly Shannon and Will Ferrell together again

— George Clooney wants you to respect Adam Sandler, dammit

— Labubu heist

— I did not know Grateful Dead fans call nitrous balloons “ice cold fatties”

— updating a story from Friday’s newsletter: AMC is cutting down the pre-movie ads after all

— the USDA is using Scarlett Johansson and Adam Driver to scare off wolves

— incredible headline: “Meet the five-time beer-mile world champion: ‘I knew I could chug from a young age’”

— “Baby Goose Abandoned by Its Parents Learns to Be a Tall Bird After Finding an 'Unexpected Family' with 3 Cranes”

— a Miami Heat security guard got busted for a seven-figure stolen basketball jersey operation

— former NFL lineman D’Brickashaw Ferguson went back to school to become a nurse, which is extremely cool (personal note: he got his degree from Thomas Jefferson University in Philly, which is the hospital I spent a few months in after my spinal cord injury, and I’ve been trying to wrap my head around how wild it would have been to be in there all goofed up on various medications and have a 6’6 student nurse named D’Brickashaw walk in my room)

— I still can’t believe Manimal was a real show

Okay, that’s it for this week. Please subscribe and upgrade and let Timothy Olyphant make Conan O'Brien squirm a little.