In the HBO sketch series “Life, Larry and the Pursuit of Unhappiness,” Larry David humorously inserts his stubborn and grumpy character into significant moments in American history. In the series, “Lawrence,” as he is sometimes referred to, participates in World War I, interrupts George Washington’s Farewell Address, and supports Rosa Parks on a Montgomery bus for reasons that are, unsurprisingly, misguided.
The series is produced by Barack Obama under the Higher Ground banner, which he shares with Michelle Obama. Appropriately, in the show’s finale, Obama revisits a key moment of his presidency. However, rather than focusing on high-profile events like the killing of Osama bin Laden, the Iran Nuclear Deal, or the legalization of same-sex marriage, the spotlight is on a more peculiar incident: the uproar caused by his choice to wear a tan suit at a 2014 press conference on ISIS. This fashion decision, which has its own Wikipedia page, was criticized as “unpresidential” by various media, including the New York Times, GQ, and Fox News.
Obama made his first appearance on “Life, Larry” to introduce the show. When David and co-creator Jeff Schaffer suggested he participate in a sketch, Obama, along with Higher Ground executive producer Ethan Lewis, proposed revisiting the tan suit controversy. “From the very beginning, my dream was to close the book on the tan suit once and for all,” Lewis remarks.
Schaffer and David crafted a “Curb Your Enthusiasm”-style alternate history where David is blamed for the fashion faux pas. In this sketch, as Obama prepares for a press conference, a mango smoothie rests on the Resolute Desk. David, wanting a sip, is refused by Obama to avoid sharing the straw. After Obama exits, David sneaks a sip, spilling the smoothie on the navy blue suit Obama had intended to wear. On his return, David tries to distract Obama from the spill by suggesting he wear the tan suit, claiming it’s “casual Friday.”
Obama agrees, trying on the lighter suit, prompting David to deliver his signature line, “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 shared with Variety that working with Obama was “one of the coolest things I’ve ever gotten the chance to do.” “Being around him makes you feel smarter and better,” Schaffer notes. “He has great improv skills, impeccable comedic timing, and is a talented actor, not just as a former president, but as an actor as well.”
Having collaborated with David since the “Seinfeld” era, Schaffer was amused to see Obama give notes to the veteran comedian. “It was funny watching him say, ‘Larry, you’re coming in late!’ He’s used to giving orders, and Larry found himself in the unusual position of being told what to do, which is rare on a Larry set.”
What was the most nerve-racking part of directing a former president?
“The first challenge was deciding how to address him,” Schaffer says. “I was directing and things were moving quickly, so I had to remember to say, ‘Sir, let’s do that one more time,’ or ‘Hold on, Mr. President.’ I didn’t want to make the mistake of saying, ‘Hey, Barack.'”
The Oval Office stage was designed by the Obamas’ interior designer, Michael S. Smith, who led the 2010 renovation of the real White House room. Smith meticulously recreated the layout and furniture, impressing Obama, who remarked, “This is unbelievable. It looks just like it was when I was here,” Schaffer recalls. The attention to detail extended to Obama’s on-screen aide, portrayed by his actual Director of Oval Office Operations, Brian Mosteller.
According to Schaffer, one of the surreal aspects of directing Obama was the conversation during the four-hour shoot’s downtime. “Sitting in the Oval Office with President Obama, listening to him talk about various topics was surreal,” he says. “He has some amusing theories.” One of Obama’s memorable opinions was: “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 leads its non-fiction and sports division, agrees: “The banter was phenomenal. Being a fly on the wall in that room was incredible.”
Despite Schaffer’s commendation of Obama’s acting skills, Lewis doesn’t foresee him pursuing more acting roles. “President Obama doesn’t have a strong desire to shift his career in that direction, but it was enjoyable to watch him act, and I’m glad it worked out for the show,” Lewis comments.
“Life, Larry and the Pursuit of Unhappiness” was initially intended as a seven-episode limited series marking America’s 250th anniversary. However, Lewis and Schaffer would be keen to continue the series. “I think it’s been successful, and we all enjoy making it,” Lewis says. “Ultimately, it’ll be up to Larry and HBO to decide, but I’d love to do more.”
Nonetheless, perhaps Obama should consider some distance from David for his own sake. “The president mentioned, ‘I enjoy being annoyed by Larry, and when we’re together, I find myself starting to sound like him,’” Schaffer says. “Larry is pulling him into his vortex of negativity.”
