A few years after Barack Obama famously joked that Drake was “able to do anything he wants,” the Canadian rapper was spotted enjoying a night out in Los Angeles with two very familiar faces from American history, Malia and Sasha Obama. The sisters, now grown into confident young women, were photographed together at a popular Hollywood club, dressed in sleek modern outfits that highlighted just how far they have come since their childhood years in the White House.
Malia, born July 4, 1998, and Sasha, born June 10, 2001, spent their formative years under extraordinary public attention. From the moment their father entered the presidency, they became two of the most recognizable children in the world. Michelle Obama has often spoken about the challenge of raising them with both protection and independence. In a conversation with Melinda French Gates on the Moments That Make Us podcast, she explained that her daughters had to learn how to move through life politely and gracefully while constantly being watched, all while forming their own identities away from their parents’ political legacy.
Barack Obama has shared many reflections on watching his daughters grow up under that spotlight. One memory he often returns to is Malia’s prom night in 2014. Seeing his daughter step into heels and formal wear for the first time felt like a turning point. He described the moment as jarring, beautiful, and deeply emotional, recognizing how quickly childhood had given way to young adulthood. Moments like that marked the gradual shift from protected presidential children to independent individuals charting their own paths.
After finishing high school, Malia took a gap year before enrolling at Harvard University, where she later graduated in 2021. Her creative interests led her into the entertainment industry, working on projects such as Extant and Amazon’s Swarm. In 2024, she made her own artistic debut at the Sundance Film Festival with her short film Heart, signaling a clear commitment to building her own career in storytelling and film.
Sasha followed a different academic route. Often described by her father as “the comedian” of the family, she attended the University of Michigan before transferring to the University of Southern California. She completed her sociology degree in 2023, approaching her studies with the same determination that defined her childhood years in the public eye.
Today, the sisters live together in Los Angeles. Michelle Obama has spoken about how comforting their closeness feels to her as a mother. She shared that knowing her daughters still choose to sit together at the kitchen table, talking and supporting one another, reassures her that the bond formed during their intense upbringing remains strong.
That shared life in Los Angeles includes an active social scene. Their recent appearance at The Bird Streets Club offered a glimpse into their young adult world. Sasha wore a cropped black corset paired with cargo pants, while Malia chose a sheer lace up top and patterned trousers. They stayed until the early hours of the morning, embracing a nightlife far removed from the formality of Washington and the strict security routines of their youth.
Drake’s connection to the Obama family stretches back years. He once joked about wanting to portray Barack Obama in a biopic, a comment that sparked widespread attention. In 2020, Obama responded with good humor, remarking that Drake “seems to be able to do anything he wants” and adding that his daughters would be perfectly fine with the casting.
The photos of the sisters enjoying their night out quickly sparked conversation online. Many saw them not as former first daughters, but as independent, stylish young women navigating adulthood on their own terms, finally free to live beyond the boundaries of the national spotlight that once defined their every step.