Drake Joins Malia and Sasha Obama for a Fun Night Out
A few years after former President Barack Obama famously remarked that rapper Drake “is able to do anything he wants,” the Canadian music icon was recently seen partying late into the night with his two young daughters, Malia and Sasha Obama. The event took place at one of Hollywood’s most exclusive nightlife venues, where the atmosphere was vibrant, energetic, and filled with music and excitement. The sight of Malia and Sasha Obama enjoying a night out alongside Drake immediately captured public attention. Both sisters were dressed in daring, fashionable outfits that reflected their transition from former first daughters to independent young women carving their own paths in the world.
Malia sported a sheer, lace-up top paired with high-waisted printed trousers that accentuated her figure, her long brown hair flowing loosely over her shoulders, while Sasha opted for a black cropped corset that revealed her midriff, complemented by slouchy, low-slung cargo pants and open-toe heels. Her hair was styled in a high ponytail with braids, and she sparkled with jewelry — rings, a necklace, and earrings — adding to her confident, youthful vibe.
The party reportedly lasted until the early hours of the morning, after which the sisters and their friends left together, continuing to enjoy the evening away from the public eye. Their appearance alongside Drake reflects not only their comfort in social settings but also the unique intersection of politics, celebrity, and pop culture that continues to define aspects of their lives.
Growing up in the White House, Malia and Sasha lived under intense public scrutiny from 2009 to 2017, when their father served as the 44th President of the United States. As daughters of Barack and Michelle Obama, they were among the most recognized children in the world, attending school and trying to maintain a semblance of normalcy despite the constant media attention. Michelle Obama has spoken openly about the challenges her daughters faced growing up in such a spotlight, emphasizing the need for them to develop resilience and independence.
“They are watched,” the former First Lady reflected during an episode of the podcast Moments that Make Us with Melinda French Gates. “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.” She described her parenting approach as preparing her daughters for life beyond the White House, stating, “Well, those girls had to be smart and confident and independent straight away, even when they were living in a house with butlers and maids and florists. But I was raising them thinking, ‘You’re not going to live here, and with me, forever. So I’ve got to hand you your life soon and let you manage it.’”
Malia Obama, born on Independence Day in 1998, had a bittersweet moment when preparing for her high school prom, as her father expressed some difficulty coming to terms with her growing up so fast. “I think it’s fair to say that the first time you see your daughter in heels is a little bit jarring,” Barack Obama shared on Live with Kelly & Michael. “She’s lovely. She’s beautiful.”
After graduating from high school in 2016, Malia took a gap year before enrolling at Harvard University, where she completed her degree in 2021. During her year off, she explored her interest in the entertainment industry, gaining experience as a production assistant on Halle Berry’s CBS sci-fi drama Extant and working as a writer on the Amazon series Swarm. In 2024, Malia made her debut as a filmmaker at the Sundance Film Festival, premiering Heart, a short film she both wrote and directed under the name Malia Ann.
Sasha, the younger of the two, was born on June 10, 2001, and has been described by her father as “just full of energy and the comedian in the family.” She graduated from high school in 2019 and began her college education at the University of Michigan, taking classes online during the COVID-19 pandemic. Most recently, Sasha earned her undergraduate degree in sociology from the University of Southern California in May 2023.
Today, the sisters live together in Los Angeles, maintaining a close bond despite their busy individual lives. Michelle Obama has expressed pride in the relationship between her daughters, saying, “It feels good to know that the two girls you raised find solace at a kitchen table with one another. It’s like the one thing you want for them.”
Their public outing with Drake highlights how Malia and Sasha continue to navigate life in the public eye while embracing their independence and growing sense of style and identity. Drake, who has shared mutual admiration with the Obama family over the years, was in Los Angeles performing at the Crypto.com Arena (formerly the Staples Center) on his “It’s All A Blur Big As The What?” tour.
The connection between Drake and the Obamas has a long history. The Toronto-born rapper once expressed interest in portraying Barack Obama in a film. In 2010, he remarked, “I hope somebody makes a movie about Obama’s life soon because I could play him.” The former president himself responded positively in 2020, saying, “I will say this, Drake seems to be able to do anything he wants. I mean, that is a talented, talented brother. So, if the time comes and he’s ready…” He also mentioned that Drake had earned his family’s approval, adding, “I suspect (my daughters) Malia and Sasha would be just fine with it.”
This recent nightlife appearance shows how far Malia and Sasha have come—from their childhood days in the White House under intense scrutiny to now embracing their adulthood with confidence and personal expression. Their night out with Drake not only reflects their evolution but also the ongoing intersection of politics, entertainment, and popular culture.
What do you think about Malia and Sasha Obama’s recent night out with Drake? Share your thoughts and let others weigh in on this glimpse into the lives of two of America’s most famous young women growing into their own identities.