Mike Sweeney started writing for Conan O’Brien 30 years ago and has been right there by his side ever since. His work has fueled not only the host’s two big late-night shows—with a tumultuous stint on the Tonight Show in between—but also his recent gig hosting the Oscars and his newest project, the travel show Conan O’Brien Must Go, which arrives Thursday, May 8, on Max.
In this episode of The Last Laugh podcast, Sweeney discusses this particularly momentous time in O’Brien’s career, including how Donald Trump‘s Kennedy Center makeover threatened to derail his acceptance of the Mark Twain Prize for American Humor (streaming Sunday, May 4 on Netflix). Instead, like with so much of their other work together, Sweeney and O’Brien found a way to marry a hopeful outlook on the world with deeply silly jokes.
When I begin our interview by asking Sweeney how he’s holding up after an unusually hectic few months of writing and producing the Oscars while also putting the finishing touches on the new season of Conan O’Brien Must Go, he jokes that he’s not OK, adding, “You’re the only person who’s asked. Even my wife hasn’t asked!”
“It’s been a crazy year,” Sweeney says, “with an intensity level that I don’t think anything else any of us were expecting.”
Adding to the overwhelming stress of it all was President Trump’s hostile takeover of the Kennedy Center, which gives out the Mark Twain Prize every year. As other artists began to cancel dates and boycott the center, Sweeney says he wasn’t sure at first whether they would go through with the award ceremony at all.
“But I think Conan had a very clear sense of it early on,” Sweeney says, noting that as comedians like John Mulaney, Sarah Silverman, Stephen Colbert and others signed on to help honor O’Brien, they realized they had an opportunity to do something meaningful.
“You have these really funny people who are all coming to Washington, and who will, I’m sure, all have something to say about the current state of affairs at the Kennedy Center,” he adds. “Wouldn’t it be better to have those great comedic voices on stage there to possibly address it in some way? As opposed to, if you canceled it, it’s just a vacuum. There’s nothing.”
Sweeney says the comedians were given “no restrictions” on what they were allowed to say and O’Brien himself told them they should “feel free to say whatever” they wanted about the current administration. And that certainly was the case as the Trump jokes flowed freely from the stage.
“It’s an honor to be here at the Kennedy Center, or as it will be known next week, the ‘Roy Cohn Pavilion for Big, Strong Men Who Love Cats,’” Mulaney said at the top of the show.
Silverman told O’Brien she missed “the days when you were America’s only orange a--hole.”
And David Letterman declared, “I’m not a historian, but I believe that history will show this will be the most entertaining gathering of the resistance ever.”
O’Brien himself closed out the night with an unusually pointed speech that used Twain’s words to not-so-subtly push back against Trump’s jingoism and xenophobia. “Above all, Twain was a patriot in the best sense of the word,” he said. “He loved America but knew it was deeply flawed. Twain wrote, ‘Patriotism is supporting your country all of the time and your government when it deserves it.’”
Sweeney read the speech before O’Brien delivered it, but says it didn’t require any input from him. “When he has something that means a lot to him, he locks in with real laser focus,” he says of O’Brien. “And he wrote everything himself for his speech. And again, to me, that was much better than just canceling the whole thing. Why mute yourself?”
Another line from O’Brien’s speech that night that stood out in light of his newest project was when he noted that Twain’s “remedy for ignorance about the world around us was to travel” quoting the author as saying, “Travel is fatal to prejudice, bigotry, and narrow-mindedness, and many of our people need it sorely on these accounts.”
Sweeney jokes that that may have just been a “cheap, tawdry plug” for Conan O’Brien Must Go, but also revealed something true about how “genuinely curious and excited” O’Brien is about the world.
“What delights him the most is making people laugh who don’t know who he is, and don’t even know English,” Sweeney says, recalling a time he watched O’Brien make a schoolroom of children in Haiti laugh with purely physical comedy. “Stuff like that really makes him happy.”
After 30 years of working together hand in hand, Sweeney has become very adept at knowing how to put O’Brien in the best position to score comedically.
“It’s not normal,” Sweeney admits of their decades-long working relationship. “We’re just an old bickering couple at this point. The good thing is I don’t remember it all, so it’s fresh to me every day. But it is unusual.”
Calling O’Brien an “amazing creative force,” he adds, “It makes it easy to be connected with someone like him.”
Listen to the episode now and follow The Last Laugh on Apple Podcasts, Spotify, or wherever you get your podcasts to be the first to hear new episodes when they are released every Wednesday.
