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

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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 Larry David and President Barack Obama.

Jeff Schaffer, David’s frequent writing partner and showrunner of Life, Larry and the Pursuit of Unhappiness, 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 its HBO run. 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.”

During a recent episode of The Hollywood Reporter podcast, I’m Having an Episode (Spotify, Amazon Music, Apple), 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: “Scotty Doesn’t Know.”)

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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 “throwing a birthday party for your friend that’s in rehab.”

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.

Especially before they shut down the methadone clinics.

I hope our friend doesn’t live in a rural area.

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. [The series is produced by Barack and Michelle Obama via their production company, Higher Ground.] How does that mix of variables color the experience?

That’s the yin and the yang of the American experience, right? Larry’s there to grouse about it, and President Obama’s there to say, “Hey, no matter how sticky things get, we can still find inspiration in each other.” It’s a comedy, so there’s a lot of Larry in here. But there are also times, especially in the beginning and the end, where we want to make sure that we’re actually saying something, too. We can get through this. And this messy, weird experiment in democracy is still is still working. We’re celebrating America, warts and all. And right now there’s a saggy orange wart that we wish would go away as quickly as possible. But the body’s still okay.

So, Larry and President Obama know one another, but this is still such a strange pairing. How did this happen?

Higher Ground and the Obamas wanted to do something to celebrate the 250th. Larry — who says “no” to everything, like you and I breathe — he’s such an American history buff. It intrigued him. I think really the the genesis of Larry’s interest starts four years ago, when Larry and I did a commercial where he played someone who was basically crapping all over the best inventions of humanity. We did it for FTX. I wonder whatever happened to them. They were so nice. (Laughs.) Anyway, remembered how much fun he had being in costume — and he forgot how much he hated being in wigs. So we just started talking about events and other things and we had some funny ideas.

I realize the president wasn’t in the writers room with you two, but what was the dynamic when the three of you were talking about the series?

The most amazing part of this was getting to see Larry and President Obama together. The first meeting we had — I’ve never met the president before — and he just says, “Do you play golf?” Not really. Then he he points to Larry and he goes, “This guy’s better than you’d think he’d be, but he wears so much sunscreen.” Obama’s just crapping all over Larry. And Larry goes, “I’m sorry my dad’s not from Kenya.” And this is minute one. These two are so funny together. So my big mission was just like, I just need to get them on screen together. That’s all I want. And when you see them on screen together, they’re so funny. It’s a very interesting odd couple.

How contemporary did you want to get with this? I think the closest to today that I’ve seen was Rosa Parks.

We go all the way up to almost today, but one thing that we really tried to do was talk about things that are happening now through a historical lens. There’s a sketch where we talk about vaccinations, but we’re not talking about vaccination issues that are happening right now. We’re talking about when the polio vaccine first came out. When you look at the history of America is that we’ve made a lot of the same mistakes again and again. We really have learned very little.

Was that helpful for you to realize, given our current strife?

We’re still around! There was a a tremendous amount of suspicion about polio vaccine when it came out. And now we’re doing that again? It’s a two steps forward, one step back progress — this American experiment. Selfishness and pettiness are not twentieth century inventions.

There are cracks at Trump in there, without any direct hits. One sketch in particular has Jimmy Kimmel playing a man who can’t fathom a president trying to seek more than two terms. Were jokes like that cathartic?

We shot that sketch in November 2025, and we knew that Trump was going to do more insane evil things between when we shot and when we aired. So we basically left spaces so we could come back and chronicle each new horror of the madness of King Trump. We know that if you give this guy a few months, he’s gonna do something else completely diabolical and stupid that we weren’t even expecting: things like sending troops into American cities to harass and even kill American citizens. That was in between starting wars with foreign countries to deflect from the fact that you’re best friends with a pedophile. We left space to come in and and refill.

You and Larry work with a lot of artistic liberty, but you’re still making this with another production company on this. What is an Obama note like?

We had one meeting, and President Obama had read roughs of the sketches. He was very complimentary. And I remember he had a note about a particular sketch and Larry just goes, “Yeah, yeah, we’ll we’ll take care of it.” And Obama just goes, “I see how this is gonna be. You know, when I was in the Oval Office, I like to think that I listened to my advisors and I took advice from them. And I was president of the United States. That’s when Larry just goes, “Yeah, but I’m president of this.” Obama spent a half an hour telling [him] how funny I think this is. One note and [he] 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?

There are things like like EuroTrip. 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.

There’s a gold record right here. We got a gold record from the single.

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 [Iraq] 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 and Saving Private Ryan. I was Ripley and The Talented Mr. Ripley. I was Will Hunting in Good Will Hunting. And I walk down the street, and people just go, “Scotty Doesn’t Know!”

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Life, Larry and the Pursuit of Unhappiness releases new episodes Fridays on HBO Max.