In his HBO sketch series “Life, Larry and the Pursuit of Unhappiness,” Larry David travels throughout history, inserting his stubborn and curmudgeonly self into America’s most pivotal moments. “Lawrence,” as he’s often called, fights in the trenches of World War I, heckles George Washington during his Farewell Address and defends Rosa Parks on a Montgomery bus (for all the wrong reasons, of course).
The show is produced by Barack Obama through his and Michelle Obama’s Higher Ground banner. So it’s only right that, in the series finale, Obama stepped in to reexamine the most historically important moment in his presidency. Not the killing of Osama bin Laden, the Iran Nuclear Deal or the legalization of same-sex marriage. No, something far more momentous and presidency-defining: the time he ignited a media firestorm by wearing a tan-colored suit to a 2014 press conference about ISIS. (The sartorial choice, which has its own Wikipedia page, saw Obama lambasted as “unpresidential,” was criticized by news outlets ranging from the New York Times to GQ to Fox News.)
Obama appeared in the first episode of “Life, Larry” to help introduce the show. But when David and co-creator Jeff Schaffer told the former president they wanted him to act in a sketch, he and Higher Ground executive producer Ethan Lewis came up with the idea to relitigate the tan suit debacle. “From the very beginning, my dream was to close the book on the tan suit once and for all,” Lewis says.
Schaffer and David then devised a “Curb Your Enthusiasm”-like revisionist history in which David (appearing to play himself) is the one to blame for the fashion crime. In the sketch, Obama is preparing for the press conference while a mango smoothie sits on the Resolute Desk. When David asks for a sip, Obama turns him down to avoid “old lips” on his straw. When the president finally leaves the Oval Office, David goes to steal a sip of the smoothie, and he ends up spilling it all over the navy blue suit Obama planned to wear. When POTUS returns, David frantically tries to divert his attention away from the mess. “I think you should wear the tan suit to the press conference,” he says, insisting it’s “casual Friday.”
Obama obliges, and tries on the lighter suit, causing David to deliver his classic, “prettay good… prettay… prettay… prettay… prettay good.” He assures Obama, “People are going to be talking about this for a long, long time.”
Art Streiber / HBO
Schaffer tells Variety that directing Obama was “one of the coolest things I’ve ever gotten the chance to do.” “It’s so cool being around him. You feel smarter and better, somehow, by just being in the area,” Schaffer says. “He had some great improv stuff. His comic timing was impeccable. He was a good actor, not just as a former president, but, like, as an actor.”
Schaffer, who has worked with David since the “Seinfeld” days, was amused by watching Obama give the septuagenarian comedian notes. “The funny thing was watching him go, ‘Larry, you’re coming in late!’ He was the president, so he’s used to telling people what to do. Larry was in the odd position of being told what to do, which never happens on a Larry set.”
The most nerve-wracking part of directing a former president?
“The first thing was: What do I call this man?” Schaffer says. “I’m directing and things are moving fast, and I have to remember, ‘Sir, let’s do that one more time.’ Or, ‘Hold on, Mr. President.’ I didn’t want to screw things up and go, ‘Hey, Barack.’”
The Oval Office stage was crafted by the Obamas’ interior designer Michael S. Smith, who led the 2010 makeover of the real White House room. Smith perfected the layout and furniture of the space, so much so that when Obama walked in, he said, “This is unbelievable. It looks just like it was when I was here,” Schaffer remembers. The attention to detail extended even to Obama’s on-screen aide, played by his real-life Director of Oval Office Operations Brian Mosteller.
According to Schaffer, just as surreal as directing the former president was chatting with him during the downtime of the four-hour shoot. “You’re just sitting in the Oval Office with President Obama, hearing him talk about stuff,” he says. “He’s got some funny theories.” He relays one of Obama’s most memorable takes: “No one should be using ketchup after age 12. That’s a child’s condiment. It’s just sugar. Use mustard! Use an adult condiment!”
Lewis, who joined Higher Ground in 2022 and serves as its head of non-fiction and sports, concurs: “The banter was phenomenal. Being a fly on the wall in that room was incredible.”
Despite Schaffer’s praise of his acting chops, Lewis doesn’t think the ex-POTUS will be rushing to add more credits to his IMDb page. “President Obama doesn’t have a great desire to make that career pivot, but it was very fun [to watch him act] and I’m glad it worked out for the show,” Lewis says.
“Life, Larry and the Pursuit of Unhappiness” was billed as a seven-episode limited series celebrating the 250th anniversary of America. Still, Lewis and Schaffer would love to extend the show. “I think it’s done well, and we all have a lot of fun making it,” Lewis says. “Ultimately, that’ll land at the feet of Larry and HBO to keep going, but I’d love to do it.”
Though, for Obama’s own good, perhaps he should spend some time away from David. “The president said, ‘I have fun being annoyed by Larry, and when we get together, I realize I start sounding like him,’” Schaffer says. “Larry is sucking him into his black hole of negativity.”