Obama to Make Comedy Debut in Larry David’s New HBO Show

PRETTY, PRETTY GOOD

The legendary comedian’s new sketch series will drop a star-studded cast into some of the most famous moments in American history.

Barack Obama is heading into one of television’s most uncomfortable places: a Larry David comedy.

But working with a former president didn’t stop David from reminding Obama who was boss.

“I’m president here,” David said, recalling a moment when Obama offered a note on one of his sketches.

Larry David and Barack Obama
Photo Illustration by Victoria Sunday/The Daily Beast/Getty Images

David revealed new details about the project—including its title, release date, and sprawling cast—during a SXSW talk in Austin alongside his longtime collaborator Jeff Schaffer, who directs the series.

The HBO sketch series Life, Larry and the Pursuit of Unhappiness: An Almost History of America, is set to premiere on June 26.

The seven-episode show will satirize U.S. history in celebration of the country’s 250th anniversary.

A short clip shown during the SXSW panel previewed the show’s brand of historical absurdity. In the sketch, David witnesses the famous “V-J Day in Times Square” moment, which is depicted by the iconic photograph of a Navy sailor kissing a stranger to celebrate the end of World War II.

Like Curb Your Enthusiasm, the series relies heavily on improvisation, with sketches built around loose outlines rather than traditional scripts. Schaffer described the concept succinctly as “‘Curb’ in costume.”

Obama, whose production company Higher Ground also produces the series, will appear opposite David in one of the sketches.

Larry David and Jeff Schaffer talking on stage at a South by SouthWest event.
Larry David and Jeff Schaffer discuss their new project at SXSW on March 13, 2026 in Austin, Texas. Mike Jordan/SXSW Conference & Festivals via

Schaffer said the former president didn’t hold back from teasing the famously prickly comedian while they worked together.

“He was ragging on [David’s] golf game, ragging on how much sunscreen [he] wear[s],” he said.

US President Barack Obama walks alongside Cyrus Walker and comedian Larry David as they play golf at Farm Neck Golf Club in Oak Bluffs on Martha's Vineyard.
Barack Obama and Larry David play golf on Martha's Vineyard on Aug. 8, 2015. SAUL LOEB/AFP via Getty Images

But Obama isn’t the only famous face to feature in the series. Each episode will feature roughly four sketches with a rotating cast of actors and comedians, including Curb regulars Jeff Garlin, J.B. Smoove, and Susie Essman, who will play women’s rights pioneer Susan B. Anthony.

Other guest stars will step into historical roles, with Bill Hader and Kathryn Hahn set to portray Abraham and Mary Todd Lincoln, while Jon Hamm and Sean Hayes will appear as the Wright brothers.

Together, the cast will step into some of the most famous moments in American history, with David, inevitably, at the center of the awkwardness.

In other words, American history—Larry David-style.

Obsessed with pop culture and entertainment? Follow us on Substack and YouTube for even more coverage.