A few years after Barack Obama joked that Drake could “do anything he wants,” the Canadian superstar has now been spotted partying with the former president’s two daughters in Los Angeles.
Recently, Malia and Sasha Obama were photographed at The Bird Streets Club, a trendy Hollywood nightspot, spending the evening with Drake while he was in town for his “It’s All a Blur – Big As The What?” tour at the nearby Crypto.com Arena.
The images quickly spread online, partly because they show just how much the former first daughters have grown up.
Growing up under the spotlight
Malia, born July 4, 1998, and Sasha, born June 10, 2001, moved into the White House as young girls and spent eight years living under constant public scrutiny while their father served as president from 2009 to 2017.
Michelle Obama has often talked about the unique pressure her daughters faced. On the Moments That Make Us podcast with Melinda French Gates, she explained that the girls had to learn early on how to handle unwanted attention politely while still building their own identities. Despite growing up in a home staffed with butlers and florists, she says she always reminded them they wouldn’t live with her forever and needed to be capable, confident, and independent.
Barack Obama once admitted that watching Malia get ready for prom in 2014 was a shock—seeing his eldest daughter in heels made him realize how quickly she was becoming an adult.
Where Malia is now
After finishing high school in 2016, Malia took a gap year before enrolling at Harvard University, from which she graduated in 2021. During that time she explored the entertainment industry, working as a production assistant on the sci-fi series Extant and later joining the writers’ room for the Amazon show Swarm.
In 2024, using the professional name Malia Ann, she wrote and directed a short film titled Heart, which premiered at the Sundance Film Festival—her first major step as a filmmaker.
Where Sasha is now
Sasha, whom Barack once described as the “comedian of the family,” finished high school in 2019. She began her college studies at the University of Michigan during the COVID-19 pandemic before transferring to the University of Southern California. She graduated from USC in 2023 with a degree in sociology.
The sisters now share a home in Los Angeles. Michelle Obama has said it brings her comfort knowing that, after everything they’ve experienced, they still turn to each other for support and companionship.
A night out in LA
Their recent night out shows that support system in action. Photos from The Bird Streets Club capture Malia and Sasha enjoying themselves with Drake and a group of friends.
Sasha wore a cropped black corset top that showed her midriff, paired with low-slung cargo pants and open-toe shoes. Her braids were pulled into a high ponytail, and she accessorized with earrings, a necklace, and rings.
Malia went for a sheer lace-up top and high-waisted printed trousers that highlighted her figure. She left her long brown hair down and finished the look with chunky boots. Reports say the group stayed at the club until around 4 a.m. before heading out together.
Drake and the Obamas
Drake’s connection to the Obama family isn’t new.
Drake’s parties must be lit 🔥 Malia and Sasha Obama attended pic.twitter.com/UxQfD5mxRP
— EM (@EXECUTIVEXMEDIA) August 25, 2023
Back in 2010, he said he would love to portray Barack Obama in a future biopic. The former president later responded in 2020, saying Drake is “a talented brother” who seems capable of doing anything—and that his daughters would almost certainly approve of the casting.
So when the rapper and the Obama sisters ended up at the same Hollywood club, it felt like a full-circle moment: the once-little girls from the White House now living their own adult lives, choosing their friends, careers, and late-night plans far from Washington, D.C.
What’s your take on their night out with Drake—just two young women enjoying adulthood in LA, or something more newsworthy?
