A few years after Barack Obama acknowledged that Drake is “able to do anything he wants,” the Canadian rapper was recently seen enjoying a night out with Obama’s two daughters.
The former first daughters, Malia and Sasha Obama, were spotted partying at a popular Hollywood venue with Drake. Both were dressed in bold, trendy outfits, with one showing off her midriff and the other wearing a revealing top.
Malia and Sasha, who have grown up in the public eye, seem to be embracing adulthood and living life on their own terms.
Life in the White House was undoubtedly challenging for the two sisters, Malia, born on July 4, 1998, and Sasha, born on June 10, 2001. From 2009 to 2017, they lived under intense scrutiny as the daughters of then-President Barack Obama and First Lady Michelle Obama.
“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,” Michelle Obama explained during a podcast interview with Melinda French Gates. She went on to highlight how she raised her daughters to be independent and confident, knowing that they wouldn’t always live in the unique environment of the White House.
Back in 2014, when Malia was preparing for her prom, her father admitted that seeing her all grown up was a tough moment. “I think it’s fair to say that the first time you see your daughter in heels is a little bit jarring,” he shared in an interview. After finishing high school in 2016, Malia took a gap year before attending Harvard University, graduating in 2021.
During her gap year, Malia explored the entertainment industry, working as a production assistant on Halle Berry’s sci-fi series Extant and as a writer for Amazon’s series Swarm. In 2024, Malia made her directorial debut at the Sundance Film Festival with Heart, a short film she both wrote and directed.
Sasha, the younger of the two, is known for her lively personality. Barack once described her as “full of energy and the comedian in the family.” After graduating high school in 2019, Sasha began her studies at the University of Michigan, later transferring to the University of Southern California, where she graduated with a degree in sociology in 2023.
Now both living in Los Angeles, the sisters share a home and, according to their mother, find comfort in each other’s company. Michelle Obama expressed joy in knowing that the two sisters have stayed close, saying, “It feels good to know that the two girls you raised find solace at a kitchen table with one another.”
The two sisters were recently spotted partying together at The Bird Streets Club in Los Angeles, accompanied by Drake. The pair wore outfits fitting for the night’s event—Sasha in a black cropped corset with cargo pants, and Malia in a sheer lace-up top paired with high-waisted printed trousers.
According to reports, the sisters partied with friends until 4 a.m. before leaving the venue.
Drake has shared a long-standing admiration for the Obamas. He has previously mentioned his desire to portray Barack Obama in a biopic, saying in 2010, “I hope somebody makes a movie about Obama’s life soon because I could play him.” When asked about this in 2020, Obama responded by saying, “Drake seems to be able to do anything he wants… I suspect my daughters would be just fine with it.”
