Several years after Barack Obama’s notable comment on Drake’s versatility, the Canadian rapper and entertainer was recently seen enjoying an animated evening out with Obama’s daughters, Malia and Sasha. The two sisters, who have grown up considerably since their days in the White House, seemed to be letting loose, having fun at a well-known Hollywood nightclub with Drake. The former first daughters dressed to match the energy of the night: one embracing a stylish midriff-baring look, while the other chose a more daring, form-fitting outfit.
From 2009 to 2017, Malia and Sasha Obama spent their formative years under intense public scrutiny as residents of 1600 Pennsylvania Avenue. They experienced an unusual childhood surrounded by constant attention and high expectations, all while simply trying to live normal teenage lives. Former First Lady Michelle Obama, reflecting on their journey, shared her thoughts on a podcast interview with Melinda French Gates. “They were watched. They had to figure out how to handle the constant attention but to do it with poise,” Michelle stated. “I wanted them to develop their own identities despite the spotlight. My goal was for them to grow up smart, independent, and resilient, even if they were surrounded by butlers and staff. I reminded them that they wouldn’t be living with us forever and that they needed to manage their lives independently.”
Happy Father’s Day to all of the amazing dads out there — and to this guy in particular. @BarackObama, thank you for being such a loving, caring, and attentive dad to our two beautiful girls. We love you so much! 💕 pic.twitter.com/mAn6O0Vcys
— Michelle Obama (@MichelleObama) June 18, 2023
As they grew older, the two sisters managed to carve out identities outside of their famous family. For Malia, born on July 4, 1998, balancing personal growth and the media’s fascination was a skill she began honing early. In 2014, when she was getting ready for her high school prom, her father, Barack, admitted on Live with Kelly & Michael that it was bittersweet seeing her dressed up and wearing heels. “Seeing your daughter in heels for the first time—it’s a little jarring,” he said, adding, “She’s lovely and beautiful.” After finishing high school in 2016, Malia took a year off before attending Harvard University. During this gap year, she explored her interest in entertainment and media, working as a production assistant on the CBS show Extant and later, writing for Amazon’s series Swarm. By 2024, she made her debut as a writer and director at the Sundance Film Festival, where she premiered Heart, a short film that marked her first major step into the creative world.
Her younger sister Sasha, born on June 10, 2001, also grew up with a unique blend of public and private life. Known for her energetic and comedic personality, she was described by Barack in 2008 as the “comedian of the family.” After high school, Sasha enrolled at the University of Michigan in 2019, taking her first classes online during the early stages of the COVID-19 pandemic. She transferred to the University of Southern California later on, where she graduated with a degree in sociology in 2023. Following her college years, Sasha now lives in Los Angeles with her sister. Michelle Obama, reflecting on her daughters’ bond, said it was comforting to know that they “find solace at a kitchen table with each other,” emphasizing the deep connection they share.
Both sisters have adapted well to life post-White House, frequently seen enjoying the freedom and independence of adulthood, sometimes attending parties and events together. Their most recent outing in Los Angeles drew attention, with fans noting the style and confidence both sisters displayed. Sasha wore a sleek black cropped corset with casual cargo pants, finishing the look with open-toe shoes. She styled her hair in a high ponytail and accessorized with statement earrings, a necklace, and rings, adding a subtle sparkle to her ensemble. Malia, staying true to her chic yet understated style, chose a sheer lace-up top paired with high-waisted patterned trousers that complemented her figure. She completed her outfit with chunky boots and let her hair cascade over her shoulders. The sisters reportedly enjoyed themselves at the club until the early hours of the morning before heading home with friends.
Their night out with Drake highlighted the mutual admiration between the Obama family and the Canadian rapper. Drake, currently on his “It’s All A Blur Big As The What?” tour, has long expressed his respect for Barack Obama and even stated his desire to play the former president if a biographical film were ever made. He mentioned in 2010, “I hope someone makes a movie about Obama’s life soon because I could play him.” Barack Obama responded positively to this idea in 2020, acknowledging Drake’s talent. “Drake seems capable of doing anything he wants,” he said. “If the time ever comes and he’s ready to take on that role, he has my household’s approval. Malia and Sasha would probably be quite comfortable with it, too.”
The two young women have remained remarkably grounded, especially given the unique circumstances of their upbringing. Raised by parents who emphasized humility, self-reliance, and service, they embody qualities nurtured both at home and within the wider world. Life at the White House was undoubtedly extraordinary but brought its own set of challenges. Constantly under the public eye, they learned how to navigate fame and maintain privacy. Michelle once mentioned that while the staff of the White House ensured comfort, she and Barack insisted their daughters be treated as normally as possible. They did household chores, studied diligently, and were encouraged to think beyond the privileges surrounding them.
Now, with their parents’ guidance and support, Malia and Sasha are charting their own paths. Malia’s creative pursuits reflect a drive to tell stories and make her mark in entertainment. Sasha, known for her vibrant personality and academic inclination, is likely exploring her interests within her field. The two sisters remain close, and their mutual support has been a source of pride for their parents. “It’s amazing to see them grown up and pursuing their dreams, but knowing they can lean on each other gives me comfort,” Michelle has said.
Their journey, though different from most, resonates with many who see the resilience and individuality they’ve cultivated. Whether they’re attending premieres, working on film sets, or simply spending time with friends, Malia and Sasha have managed to maintain authenticity and warmth. The influence of their parents, both of whom are respected globally, has likely been a foundation for their confidence and curiosity.
In many ways, Malia and Sasha Obama continue to captivate people’s attention not because of their famous family but due to their unique blend of grace, intelligence, and relatability. Their ability to transition from life in one of the most powerful residences in the world to a life of personal ambition and expression reflects their maturity. Their outing with Drake is just one of many memorable moments that illustrate their growth and independence, adding yet another chapter to their already fascinating lives.