A few years after Barack Obama remarked that Drake “can do anything he sets his mind to,” the Canadian superstar was seen letting loose with the former president’s two daughters.

Malia and Sasha Obama were photographed alongside the rapper at a trendy Hollywood nightclub, both dressed in revealing outfits—one showing her midriff and the other wearing a daring top.

Growing up in the White House certainly came with challenges for Malia and Sasha Obama, who were just kids wanting a normal life.

Malia—born July 4, 1998—and Sasha—born June 10, 2001—spent 2009 to 2017 under intense public scrutiny while living at 1600 Pennsylvania Avenue.

“They’re always being watched. They had to learn how to handle attention they didn’t ask for, but do so gracefully. They had to build their own identities in the spotlight without being consumed by it,” Michelle Obama said on the Moments that Make Us podcast with Melinda French Gates.

She continued, “Those girls needed to be strong, confident, and independent from the start, even though they were living in a house with staff. I always reminded myself, ‘They won’t be here with me forever. I need to prepare them to take charge of their own lives.’”

Malia

Back in 2014, when Malia prepared for her prom, Barack admitted he struggled with seeing his eldest daughter so grown up.

“The first time you see your daughter wearing heels, it throws you a bit,” he told Live with Kelly & Michael. “She’s lovely. She’s beautiful.”

After finishing high school in 2016, she took a gap year before enrolling at Harvard University, graduating in 2021.

During her year off, Malia explored the entertainment industry, working as a production assistant on Halle Berry’s CBS series Extant and later joining the writing team for Amazon’s Swarm.

In 2024, under the name Malia Ann, she premiered her short film Heart—which she wrote and directed—at the Sundance Film Festival.

Sasha

Barack told People in 2008 that Sasha was “full of energy and the comedian of the family.”

Following her 2019 high school graduation, Sasha began classes at the University of Michigan, studying online during COVID-19.

She later transferred to the University of Southern California, earning her sociology degree in May 2023.

The sisters now share a home together in Los Angeles.

“It makes me happy knowing the two girls we raised find comfort around the same kitchen table,” Michelle Obama shared. “That’s all you really want for them.”

All grown up

Malia and Sasha also find comfort in spending nights out together.

Recently, the two were photographed partying late into the night with Drake at The Bird Streets Club in Los Angeles.

Both wore bold, skin-baring outfits suited for the venue.

Sasha paired a cropped black corset with low-rise cargo pants and open-toe heels. Her braids were tied in a high ponytail, and she accessorized with sparkling jewelry.

Malia matched her sister’s relaxed vibe, wearing a sheer lace-up top with high-waisted patterned pants that accentuated her figure. She wore her long brunette hair loose and finished the look with chunky boots.

Reports say the sisters stayed at the hotspot until about 4 a.m. before leaving with friends.

Obamas & rap royalty

Drake—who has long shared a mutual admiration with the Obama family—was in Los Angeles performing his “It’s All A Blur Big As The What?” tour at the Crypto.com Arena.

The rapper has previously said he’d love to play Barack Obama in a biopic someday.

“I hope someone makes a movie about Obama’s life, because I could play him,” he said back in 2010.

In 2020, Barack responded warmly to the idea.

“Drake seems capable of anything,” he said when asked about the rapper’s interest. “He’s incredibly talented. If the time comes and he’s ready…”

He added with a smile, “More importantly, Drake has my household’s seal of approval. I think Malia and Sasha would be perfectly fine with it.”