Malia Obama's Sly Jab At David Letterman Proves She's The Funniest In The Family

David Letterman might be a legend in the showbiz world, but not even this lifetime TV personality's star power was enough to save him from getting roasted by Malia Obama on a visit to the White House. During the inaugural episode of Letterman's Netflix interview series, the "My Next Guest Needs No Introduction" host shared his hilarious anecdote about the then-teenager with her father, former President Barack Obama.

According to Letterman, he first met Barack's two daughters, Sasha and Malia, at a White House event. The television star approached Malia to thank her, saying, "You don't know who I am. I know your mother and father. My name is Dave Letterman, and I am very happy to be here." He then thanked Malia for the invitation to the party, to which she replied, "Yeah, you look like a guy who really knows how to party."

Letterman, the former president, and the show's audience burst into laughter over Malia's sly jab, and the television host called the interaction "absolutely delightful." According to her father, her not-so-subtle dig at Letterman was just one example of his daughter's keen humor.

After David Letterman shared his story of meeting Malia Obama for the first time, her father and former President Barack Obama immediately beamed with pride. "That was a pretty good line," Obama told Letterman, smiling. "She's a riot. She is funny." Malia's goodhearted one-liner at Letterman's expense wasn't the only time the former president has publicly lauded his daughters' sharp wit and impeccable way with words — even if it's at his expense.

While speaking to Dax Shepard on the "Armchair Expert" podcast in July 2021, Barack revealed that Malia and Sasha Obama have plenty of practice roasting people. In fact, he's been their primary test audience. When Shepard asked Barack if his daughters gave him special treatment because of his presidential accolades, the ex-POTUS was quick to say no.

"I am generally the brunt of every joke in the household. At the dinner table, [Malia, Sasha, and Michelle] just mock me constantly about my big ears or my weird habits or fashion sense or if I mispronounce the name of some hip-hop star that Sasha's been listening to. They all go, 'What an idiot.' So, that's basically the vibe at my house," Barack admitted with a laugh. It might not be the sweetest of Barack's father-daughter moments with Sasha and Malia, but it's definitely up there for the funniest. 

Barack Obama praised his eldest daughter, Malia Obama, for her strong wordsmithing skills while on David Letterman's "My Next Guest Needs No Introduction." He said Malia often presented him with things she wrote, expecting he would read them and offer notes immediately. The former president said that while Malia would happily debate him on his critiques, her younger sister, Sasha Obama, only ever agreed to share her writings (which Barack said were equally impressive) if he agreed not to speak to her about them afterward.

Malia's extensive history of writing, workshopping, editing, and revising has been useful to her as she forges her own career in Hollywood. The former presidential kid's television writer debut was on "Swarm," Donald Glover's 2023 dark comedy. Showrunner Janine Nabers spoke to Entertainment Tonight about working with Malia, saying, "Some of her pitches were wild as hell, and they were just so good and so funny. She's really, really dedicated to her craft."

The eldest Obama daughter took a more solemn approach with her 2024 contribution to the Sundance Film Festival, which garnered her flack from critics who were upset after Malia Obama changed her professional name. But whether she opts to use her surname going forward or not, it's clear that Malia has embodied the quick wit, sharp humor, and self-starting attitude she inherited from her parents, Barack and Michelle Obama.