A few years after Barack Obama famously said Drake was “able to do anything he wants,” the Canadian superstar was spotted letting loose in Los Angeles—this time in the company of his former admirers: Malia and Sasha Obama.
The sisters, who grew up under the nation’s microscope, were photographed partying with the rapper at a Hollywood hotspot, dressed in sleek, modern outfits fit for a night out. For many, it was a reminder of just how grown up the former first daughters are now.
Malia, born on July 4, 1998, and Sasha, born June 10, 2001, spent eight pivotal years inside the White House fishbowl. They arrived at 1600 Pennsylvania Avenue as children and left as young women, navigating pressure, scrutiny, and intense public interest.
Michelle Obama has often spoken about the balancing act her daughters had to learn early on. In a conversation with Melinda French Gates on the Moments That Make Us podcast, she said, “They are watched. They had to learn how to balance the unwanted attention, but do it politely… to build their own lives in the spotlight and not be eaten up by it.” She added that despite the support they had—including staff, schedules, and structure—she raised them to be independent: “You’re not going to live here, and with me, forever.”
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For Barack Obama, one moment in 2014 made that reality sink in—Malia preparing for her prom. “The first time you see your daughter in heels is a little bit jarring,” he admitted on Live with Kelly & Michael. “She’s lovely. She’s beautiful.”
After graduating high school in 2016, Malia took a gap year before enrolling at Harvard, where she graduated in 2021. She used her time off to explore her creative ambitions, working on productions like Extant and eventually joining the writing team for Amazon’s Swarm. In 2024, under the name Malia Ann, she debuted her short film Heart at the Sundance Film Festival—her first major step as a writer-director.
Sasha, described by her father as “the comedian in the family,” completed her own academic path. She began college at the University of Michigan during the pandemic and later transferred to USC, where she graduated with a degree in sociology in 2023.
Today, the sisters share a home in Los Angeles. Michelle Obama said knowing they’re close brings her enormous comfort: “It feels good to know that the two girls you raised find solace at a kitchen table with one another.”
And part of that shared life includes nightlife. Recently, Malia and Sasha were seen partying at The Bird Streets Club with Drake, who is touring his “It’s All A Blur—Big As The What?” show at the nearby Crypto.com Arena.
Both women embraced bold, evening-ready looks. Sasha wore a cropped black corset showing her midriff, pairing it with loose cargo pants and open-toe shoes, her braids swept up in a high ponytail and her jewelry glinting under the club lights. Malia opted for a sheer lace-up top and high-waisted printed trousers that flattered her silhouette, finishing the look with chunky boots and her long brown hair flowing freely.
According to reports, they stayed until about 4 a.m. before leaving with friends—two adults living their own Californian chapter far away from the rigid formality of Washington.
Drake’s connection to the Obamas goes back years. In 2010 he expressed interest in portraying Barack in a future biopic, saying, “I could play him.” The former president later responded in 2020 with warmth and a hint of amusement: “Drake seems to be able to do anything he wants… If the time comes and he’s ready…” He added that his daughters “would be just fine with it.”
The photos from the Los Angeles outing sparked plenty of conversation online, not just about their friendship with the musician, but about how fully the Obama daughters have grown into their own lives—independent, stylish, and navigating adulthood on their own terms.
What do you think about their night out? Feel free to share your thoughts and pass this story along—everyone has an opinion when it comes to the Obamas, Drake, and a Hollywood weekend.
