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‘Life, Larry and the Pursuit of Unhappiness’ Showrunner Jeff Schaffer on Working With Obama (and Navigating Trump) With Larry David

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‘Life, Larry and the Pursuit of Unhappiness’ Showrunner Jeff Schaffer on Working With Obama (and Navigating Trump) With Larry David
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The longtime David collaborator knows that 2026 is both a fitting and bizarre time to be feting the U.S.: 'We’re celebrating America, warts and all. And right now, there's a saggy orange wart.'

Of all the ways in which people have decided to celebrate the 250th anniversary of the United States of America, few are as left-field as a sketch comedy collaboration between, seems as aware of this as anyone.

But when the Obamas and their Higher Ground productions company expressed an interest, who was he to turn them down? The fruits of their labor, a seven-episode exploration of American history through David’s curmudgeonly eyes, is already halfway through itsrun. And, yes, it’s even a little educational.

“I enjoy history, but I like ancient history — Greek and Roman stuff,” says Schaffer. “But Larry’s American history knowledge was astounding. He wanted to do something on winning the popular vote but losing the election, and he goes ‘You know, like Samual J. Tilden. ’ Who?

He could have been a country music star for all I knew. ”), Schaffer talked about collaborating with a former president and making a production schedule that would accommodate the erratic behavior of the sitting one.

(And, for good measure, he discussed one of the more unlikely gems of his long comedy career: “ You and Larry David were in conversation at South by Southwest earlier this year, and you compared a series celebrating the country right now to “He’s at the methadone clinic right now. He’s all fucked up, but we still love him. So we’re gonna celebrate him and we hope he gets better soon.

For many, this was not a “rah rah” Fourth of July. But, also, it’s a time to acknowledge the country’s history and you’re working with a beloved former president. how funny I think this is. One note and gets into a defensive crouch. ” But they did give very good notes.

And for certain sketches, which we haven’t gotten to yet, they were their knowledge was instrumental. Looking at your long résumé, what is something that you worked on that you thought should have hit bigger than it did?. Alec Berg and Dave Mandel and I wrote that, and I directed. When it came out, not that many people saw it.

But thanks to DVD, it has had this life. The song “Scotty Doesn’t Know” is like having some sort of renaissance that I don’t understand. A lot of my friends’ kids are in college, and they’re sending me stuff of bars singing “Scotty Doesn’t Know” when it comes on. I guess that we were disappointed that more people didn’t see it when it came out.

But it’s had the life that we wanted it to have. We wanted to make a movie for teens to watch together in their parents’ basement while stealing their parents’ liquor. That’s happened. That movie came out when I was mid-college and, by senior year, “Scotty Doesn’t Know” was playing at most parties.

We’ve never spoken about this, so can you tell me how that all came together? Matt Damon making a cameo as a pop-punk frontman was an unexpected way to start that movie. Alec, Dave and I, along with the band Lustra, wrote the lyrics. Obviously, the band came up with an amazing hook.

We were shooting this movie in Prague during SARS and the war. We didn’t have a lot of money. We couldn’t be flying people in. Matt was shooting The Brothers Grimm in Prague.

His head was shaved because he was wearing a wig the whole time. He’d quit smoking, so, in his words, he had swelled up like a tick. So we were like, “Hey, do you want to do this? ” He had one one night available, which was the shortest night of the year.

It was literally June 21st. There’s like five hours of nighttime to get this thing done. But he was so fun, and we just raced to get it. It’s crazy that it even existed. If Matt hadn’t been there.

If he hadn’t looked like that. It just all came together. I was talking to Matt a little while ago, and he was like, “I was Private Ryan andThe Hollywood Reporter is a part of Penske Media Corporation. © 2026 The Hollywood Reporter, LLC. All Rights Reserved.

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