Drake Steps Out With Malia and Sasha Obama for a Glamorous Hollywood Night

Michelle Obama Playfully Recalls Daughters Hosting Her and Barack for Cocktails: 'Martinis Were a Little Weak'

It was a star-studded sighting no one saw coming — Drake, Malia, and Sasha Obama stepping out together for a night on the town in Los Angeles.

A few years after former president Barack Obama famously said rapper Drake “can do anything he wants”, the Canadian superstar was spotted enjoying a late-night hangout with the former first daughters at one of Hollywood’s most exclusive clubs.

A Stylish, Star-Studded Scene

According to eyewitnesses, the trio arrived separately but joined up inside, where they partied with friends and mingled with other celebrities. Malia and Sasha — now in their 20s — turned heads with looks that perfectly balanced confidence and effortless cool.

Malia, 26, rocked a sheer lace-up top paired with high-waisted patterned pants, while Sasha, 23, went edgy-chic in a black corset, low-slung cargo pants, and heels. “They looked relaxed, confident, and totally in their element,” one onlooker shared.

The sisters reportedly stayed until the early hours before heading off with friends to continue the night — far from cameras but very much the talk of the town.

From White House Kids to LA It-Girls

The Obama sisters have come a long way from their days growing up in the White House. Once known for shy smiles at state events, Malia and Sasha are now full-fledged adults carving out their own creative and professional paths — all while staying close and grounded.

Former First Lady Michelle Obama has often spoken about her daughters’ journey from presidential daughters to independent women, saying she wanted to raise them to be “smart, confident, and independent straight away.”

And it shows.

Malia, born in 1998, graduated from Harvard University in 2021 and recently made her directorial debut with the short film Heart, which premiered at the Sundance Film Festival earlier this year.

Sasha, born in 2001, earned a degree in sociology from the University of Southern California in 2023. The sisters now share a home in Los Angeles, where they’re often spotted grabbing coffee, attending concerts, and enjoying the creative freedom the city offers.

A Friendship Years in the Making

Drake’s connection to the Obama family isn’t exactly new. The Grammy-winning rapper once admitted he’d love to play Barack Obama in a biopic — and the 44th president gave his approval, calling Drake “a talented brother” who could pull it off.

So when fans saw photos of the rapper and the Obama sisters out together, social media naturally went wild.

“Drake hanging with Malia and Sasha? That’s presidential levels of cool,” one user joked on X. Another wrote, “Barack’s gotta be smiling somewhere.”

While the group has kept details of their outing private, the sighting felt symbolic — a full-circle moment that showed just how much Malia and Sasha have grown into their own spotlight.

Living Under the Lights — On Their Own Terms

As daughters of one of the most recognizable families in the world, the Obama sisters have spent their lives balancing privacy and fame. But in recent years, they’ve embraced adulthood with poise, showing the world that they’re more than just political legacies.

Their night out with Drake wasn’t about glitz or gossip — it was about freedom, friendship, and stepping fully into their identities as young women living life their way.

Whether they’re walking a red carpet or just out for a late-night laugh, Malia and Sasha Obama continue to prove one thing: growing up in the spotlight doesn’t mean losing your shine — it just means learning how to own it.