Larry David’s new series Life, Larry and the Pursuit of Unhappiness, which has just wrapped on HBO Max with a sketch featuring former US president Barack Obama, has provided plenty of talking points over the past couple of months.

For fans of Curb Your Enthusiasm, it’s essentially been a reunion, featuring most of the show’s former stars as well as that sitcom’s unrelenting cringe comedy. Released as a “warts and all” celebration of America’s 250th birthday, it’s also been unafraid to take shots at the country’s current leadership including Donald Trump and Robert F. Kennedy Jr. The sketch which was most critical of Trump also served as the last screen credit for legendary filmmaker Rob Reiner (a vocal critic of the president), filmed just a month before his tragic death.

For David, however, this project has been 50 years in the making – born via niche gags in 1970s comedy clubs and fostered through a lifelong obsession with history. Deputy TV editor Meg Watson spoke with David’s long-time collaborator and series co-creator Jeff Schaffer about doing improv with a former president, the state of comedy in 2026 and why Larry David would “love” to be cancelled.

**MW: Congrats on the show! I can only imagine how fun it must have been to work on this project: some of the world’s best comedians playing dress up, hanging out with Larry. **

JS: That was the selling point for all the amazing people who came in! “Hey, come in for a day and play with Larry”. Every day was a new group of actors. Every day was new wardrobe, new hair and make-up, a new period – and I think that’s the real fun of the show. Each one had a surprise element. It was like historical Russian roulette.

We knew we wanted to bring Jon Hamm in, for example. We had him earmarked for another part, but he couldn’t do it because he’s in 10 of the 12 television shows on the air right now. He said, “I really wanted to do something, but I can only do this one day”. So we were like, “Well OK then, you’re a Wright brother!”

I’m really thrilled that we got to play with so many of the people not only in our Curb family, but our extended Curb family: Bill Hader and Jon Hamm and Sean Hayes and Lin-Manuel Miranda and Vince [Vaughn]. It was a blast to see everybody. [Note: Cheryl Hines, however, who played Larry’s wife on Curb and is now married to US Health Secretary Robert F. Kennedy Jr – who is openly mocked in the series – is a notable omission.]

**How did you decide what events to include? I like that it’s as you’ve said, a “warts and all” history. There’s some dark stuff in there – from slavery to antisemitism, and suicide during the Great Depression. You wouldn’t look at that and think, “That’s going to make a great comedy sketch”. **

We started making a big list of events – and some are obvious, right? Like the Declaration of Independence. You do a little research and you realise, oh, everyone thinks Thomas Jefferson wrote it, but there was actually this group of five: Thomas Jefferson, John Adams, Ben Franklin and also Roger Sherman and Robert Livingston. You’re like, “OK, that’s how we get in.” Larry is Robert Livingston. Larry gets his crack at it. Everyone hates it. He was ignored by history.

And then there are other big hits where he’s not ignored by history. Instantly, we were like: Larry’s the guy who told Lincoln to go see that play. That’s Larry, right?

And honestly, he knows so much about American history [it came very easily for him]. You can tell that this has been an obsession.

If you look at his old stand-up, he actually had jokes about Jonas Salk’s mother in comedy clubs in the ’70s. And then obviously if you’re going to talk about [the inventor of the polio vaccine], we wanted to talk about vaccines now. We brought in the RFK stuff, and it all just sort of fell together.

But Larry’s always had historical references in his old act that, frankly, no one appreciated. This was his chance to go, “You didn’t like it before, so I’m gonna rub it in your faces now!”

Were there conversations about how recent to make that history? Obama’s last sketch is the latest, set in 2014, but it’s an outlier. Was there a moment you considered, “Do we want to include the Capitol insurrection? Is there a way into 9/11?”

I remember we talked about a sketch about the Charlottesville race rally [which happened in 2017]. You know, “Jews will not replace us”. We had joked around about Larry playing a Jewish guy, going, “I don’t want that. I don’t want to be a toll-booth attendant or a janitor!” But it went as far as that. We were like, “Eh, that has no legs”.

But we knew we wanted to end with [former] president Obama. They were so funny together.

“I always joke that I know where the line is because I can look back and see it.”Jeff Schaffer, Larry David’s long-time collaborator

How did you feel about directing a former president? You’ve directed plenty of big stars, but this is someone who directed the armed forces... Does it change the dynamic?

Well, the first thing I asked, talking to our partners at Higher Ground [the production company owned by the Obamas], was, “What do I call him? How do I address him?” And they just said, “For you, I’d stick with sir.”

But no, it was so good. He and Larry are so good together. It felt like a Curb sketch. It was the most amazing experience I’ve ever had, just sitting in an Oval Office with president Obama and Larry … These are his words: he said, “I really enjoy being annoyed by Larry.”

I can imagine that’s a special experience – though maybe less so for you, after so many years.

He and I have been working together – on and off, mostly on – since I was 24. It’s literally the longest relationship I’ve ever had. I don’t know what that says about me, but I still enjoy it very much.

I know this show was written in the same way you did Curb: you write an outline and work out a lot of the details through improv. Did Obama ad lib his own jokes?

I mean, president Obama telling Larry that he has “old lips” and calling him “old lips” – that’s a straight-up Obama improvisation. That was all him. The first time he did it, Larry lost it. He was laughing for, like, five minutes. And then that got woven into the rest of the scene.

How often does Larry break like that? Is it a real achievement?

I would love to praise Obama and say that it’s a rare thing to get Larry to break, but it is not. He loved doing the show, he’s having fun and he laughs all the time. The number of takes that are ruined because of him... [Schaffer shakes his head]. He’s really having fun.

Obama’s famously pretty funny, at least in comparison to other politicians. There was his appearance on Between Two Ferns and his bit with Keegan-Michael Key at the Correspondent’s Dinner...

He wasn’t good for a former president; he was good for someone in a sketch show!

Did you feel any hesitancy about bringing him into scenes like that, though? All those bits that he was known for were during his presidency, it was pre-2016 – and that felt like a real turning point for how we interacted with politicians, how much we let them into the joke. Did you worry it could be a comedy killer?

Well, the problem now, in this age, is that the president is the joke. We’re sort of in a post-comedy world with our politicians. But no, he was great. I always knew that he and Larry were going to be funny. The two of them have such a good dynamic. They like ragging on each other.

There’s a lot in the series about Trump without talking about Trump. That sketch where Rob Reiner plays George Washington, denouncing any theoretical president who would try to run for a third term, is such a direct hit. Did you have concerns about how it would be received? It features Jimmy Kimmel, who copped a lot more for saying a lot less. And the things that Larry says in that scene are pretty hardcore. Were there any difficult talks with HBO or the lawyers about how far to take it?

Not one. That never even crossed our minds. I mean, look: we did the MAGA hat episode on Curb, and he ended up pinning it on his Truth Social. He was so dumb he didn’t know we were making fun of him. It’s just crazy.

We shot the George Washington scene in November 2025, and we knew that Trump was going to do more crazy, stupid things in the interim. We came back in March and shot Larry doing a few more lines because so many new things had happened: sending ICE in and killing American citizens, starting a war to try to distract from the fact that you’re best friends with a paedophile. Larry couldn’t care at all [about political or legal blowback]. I mean, I always thought this with Curb, too: if you told me that he was making this just to put on his shelf, he would do it the exact same way.

Obviously when we did it, we had no idea that Rob [Reiner] was going to pass away a month later, which gave it this whole extra charge and poignancy. I’m very saddened by the circumstances that led to it being that way. And I don’t just mean Rob’s tragic passing. I also mean the ignorance and misinformation that’s created the situation we’re in. But I’m really happy that Rob got the last word. That was special.

**How are you feeling in general about the state of comedy? Rainn Wilson from The Office recently made headlines saying that because everything has to be “politically correct” these days, you can’t make the kind of TV you used to. That caused a lot of debate, and some people sharing clips from Curb (which ended in 2024) as evidence to the contrary. **

As someone who has almost exclusively made comedy that is not “politically correct”, do you think we can still joke in the same way?

I haven’t found that to be true. But I also get to work with someone who doesn’t care at all. I mean, someone asked [Larry], “don’t you worry about being cancelled?” and he was like, “Oh, I’d love to be cancelled. That’d be amazing.”

I always joke that I know where the line is because I can look back and see it. I get it. But I don’t think anything should be off-limits. It’s all [in] the execution. It’s all about how you do it. And I think it’s really important not to care – not about the comedy, but about the audience [response].

HBO has been so great about artists making the thing that they like, and letting the audience decide. People don’t have to watch it. There’s plenty of UFC to watch.

I mean, you’ve worked with Sacha Baron Cohen [co-writing Bruno and The Dictator], who’s notorious for that kind of comedy. He’s coming back with a new Ali G film, so we can’t be too restricted.

Sacha, who’s brilliant, is always very aware of the target. He’s either holding up a mirror to stuff or he’s punching up, not down. He always has a satirical point.

Maybe I’m lucky, or I’m sheltered, or I’m just on my way out. But I’ve never really worried about what people are going to think. I guess I want people to go, “Holy shit! I haven’t seen that before. Or I can’t believe they did that”. That’s what I’m actually going for.

Life, Larry and the Pursuit of Unhappiness is on HBO Max now.

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