A few years after Barack Obama famously joked that Drake could play him in a biopic because the rapper “can do anything he wants,” the Canadian superstar ended up sharing a very different moment with the former president’s daughters. Late one night in Los Angeles, Drake was spotted partying with Malia and Sasha Obama—two women who grew up under nonstop national scrutiny and are now living their own adult lives far away from the rigid formality of Washington.
The sight of the three together sent the internet into a frenzy. For many, it was a jarring reminder of how fast time moves. The little girls who entered the White House in brightly colored coats and hair bows are now full-grown women with careers, apartments, opinions, and nightlife of their own.
Malia Obama, born on July 4, 1998, and Sasha, born June 10, 2001, spent eight defining years at 1600 Pennsylvania Avenue. They arrived as children and walked out as young adults who had navigated one of the most intense and invasive environments imaginable. Michelle Obama has spoken often about the discipline it took to raise normal kids in abnormal conditions. She once told Melinda French Gates that her daughters had to learn early how to handle attention they didn’t ask for. “They are watched,” she said. “They had to learn to balance unwanted attention politely, without letting it consume them.” She added that, despite the structure and staff built around them, she never allowed them to believe that life inside the White House would shield them forever. “You’re not going to live here with me forever,” she told them. The message was clear: independence is coming, and you need to be ready for it.
Barack Obama had his own moment of shock watching his daughters grow up—a moment he shared on Live with Kelly & Michael when he described seeing Malia leave for her prom. “First time you see your daughter in heels is a little bit jarring,” he said. He paused and softened before adding what every father eventually learns: “She’s lovely. She’s beautiful.”
After finishing high school in 2016, Malia took a gap year and jumped into creative work, spending time on film sets and gaining firsthand experience in the industry she’d been eyeing for years. She later enrolled at Harvard and graduated in 2021. She worked on projects like Extant and then joined the writing team for Amazon’s Swarm. In 2024, using the professional name Malia Ann, she premiered her own short film, Heart, at the Sundance Film Festival. It was her first real step into the industry not as a celebrity kid, but as a filmmaker in her own right.
Sasha charted her own path too. Described by her father as “the comedian in the family,” she began her college years at the University of Michigan before transferring to USC, where she earned her sociology degree in 2023. She’s been carving out her own space in Los Angeles with her signature mix of humor, confidence, and low-key charm.
Today, the sisters share a home in L.A., a detail Michelle Obama says brings her a sense of peace. “It feels good to know that the two girls you raised find solace at a kitchen table with one another,” she said. They cook together, argue over dishes, borrow clothes, and show up in each other’s social lives the way sisters do when they’ve survived something enormous together.
Part of that life now includes nightlife. Recently, eyewitnesses and photographers spotted Malia and Sasha at The Bird Streets Club, one of Hollywood’s current hotspots. Drake, who’s been performing his “It’s All A Blur—Big As The What?” tour at the nearby Crypto.com Arena, was also in attendance. The three were seen in a small VIP section with a group of friends, relaxed, laughing, and dancing—just adults enjoying a night out, but a sight that still carries symbolic weight for many Americans who watched the sisters grow up in the political spotlight.
Both women arrived dressed for the night. Sasha stepped out in a cropped black corset that showed her midriff, paired with loose cargo pants and open-toe heels. Her braids were pulled into a high ponytail, her jewelry catching the light every time she moved. She looked confident, loose, alive in a way only a 20-something in Los Angeles can.
Malia wore a sheer lace-up top paired with high-waisted printed trousers that highlighted her tall, slender frame. She finished the look with chunky boots, her long brown hair flowing down her back. She looked effortlessly stylish—far from the formal dresses of White House holidays, far from the cameras she once had to dodge.
The sisters reportedly stayed until about 4 a.m., leaving the club with friends after Drake and his group slipped out a side exit. The sight of them walking into the chilly early-morning air sparked immediate reactions online. Some people were shocked, some amused, others simply proud to see two young women living life on their own terms after spending their childhoods in a bubble.
Drake’s relationship with the Obamas isn’t new. In 2010, he publicly said he’d love to play Barack Obama in a future biopic. Obama, in his steady deadpan style, said years later that if someone had to portray him, Drake “seems to be able to do anything he wants.” He added that his daughters “would be just fine with it.” That comment resurfaced immediately after the party photos appeared, fueling jokes that the rapper was simply doing “research.”
Still, the story isn’t really about celebrity gossip. It’s about two young women who spent their most vulnerable years in the public eye and are now—finally—writing their own chapters. They’re navigating adulthood in a city built on dreams and chaos, building careers, friendships, and experiences that have nothing to do with politics and everything to do with who they are becoming.
The photographs from that night captured more than fashion or celebrity proximity. They captured a simple truth: Malia and Sasha Obama are no longer symbols or political footnotes. They’re adults—living life loudly, quietly, boldly, messily, privately, publicly, however they choose. And they don’t owe explanations for enjoying a weekend in Hollywood, no matter who else is in the room.
Their father once said that raising them was the greatest honor of his life. Nights like this show that he and Michelle didn’t just raise daughters—they raised women who know exactly how to stand in their own lives without apology.
And in Los Angeles, that might be the most valuable skill of all.