A few years after Barack Obama famously said Drake was “able to do anything he wants,” the Canadian rapper was spotted partying in Los Angeles with his former admirers: Malia and Sasha Obama. The sisters, now young women, were photographed at a Hollywood club dressed in sleek, modern outfits, a reminder of how far they’ve grown since their White House years.
Malia, born July 4, 1998, and Sasha, born June 10, 2001, spent their formative years under intense public scrutiny. Michelle Obama has often spoken about teaching them to balance attention with independence, telling Melinda French Gates on the Moments That Make Us podcast that her daughters had to navigate life politely in the spotlight while building their own identities.
Barack Obama recalled a defining moment in 2014: Malia preparing for her prom. “The first time you see your daughter in heels is a little bit jarring,” he said. “She’s lovely. She’s beautiful.” These experiences highlighted the transition from childhood under public watch to adulthood on their own terms.
After high school, Malia took a gap year before attending Harvard, graduating in 2021. She pursued creative projects, including work on Extant and Amazon’s Swarm, and debuted her short film Heart at Sundance in 2024. Sasha, described by her father as “the comedian,” studied at the University of Michigan and USC, earning a sociology degree in 2023.
Today, the sisters live together in Los Angeles. Michelle Obama said their closeness brings her comfort: “It feels good to know that the two girls you raised find solace at a kitchen table with one another.” Part of that life includes nightlife, as seen during their recent outing at The Bird Streets Club.
At the club, Sasha wore a cropped black corset with cargo pants, while Malia opted for a sheer lace-up top and printed trousers. They stayed until about 4 a.m., embracing a nightlife far removed from Washington’s formality.
Drake’s connection to the family dates back years, including joking about portraying Barack in a biopic. Obama responded in 2020, noting Drake “seems to be able to do anything he wants” and that his daughters would be fine with it.
The photos of the night out sparked conversation online, showcasing the Obamas’ daughters as independent, stylish, and navigating adulthood on their own terms, far from their early years in the national spotlight.