Drake Celebrates 40 With a Big Rolex, Free Birkins, and the Backstreet Boys

You only turn 40 once, and Drake made sure to usher in his fifth decade with a birthday extravaganza to remember. There were surprise performance by the Backstreet Boys, Hermès and Chanel handbags handed out as party favors, and cash prizes reaching an eye-watering $1 million. Drizzy’s outfits were just as extravagant across his entire birthday weekend.

On Friday night, Drake welcomed more than 400 guests to New York’s Casa Cipriani for the first of two birthday celebrations, swapping his recent bohemian proclivities for something more dapper. Just a day earlier, he’d been spotted enjoying a pre-birthday dinner at Mamo in Manhattan, wrapped in a chestnut-brown fringed shawl that wouldn’t have looked out of place in Sienna Miller’s fall wardrobe. But for the main event, the rapper was firmly in black-tie mode, opting for a sparkling black tuxedo jacket with silk lapels, pleated and wide-legged suit trousers, a crisp white shirt, and a satin bow tie adored with a diamond “D” pin.

Never one to exercise restraint when it comes to his wristwear, Drake brought out his one-of-one, diamond-encrusted Rolex Cosmograph Daytona, reportedly worth multiple millions. The watch is engraved with the phrase “Freeze the World,” a lyric from his song “Make Them Know” off “Iceman.” An appropriately ostentatious finishing touch for a man with a heart-stopping collection of rare timepieces, custom jewelry, and highly coveted Hermès Birkins in a litany of colors.

The rapper was equally generous when it came to accessorizing his guests. According to People, partygoers were gifted Chanel and Hermès handbags, and a game-show-style giveaway saw cash prizes starting at $10,000 and climbing to a staggering $1 million. Forget the usual birthday goodie bag, someone walked away with a flap bag and a Kelly.

The entertainment was a nostalgic affair. The Backstreet Boys took to the stage to perform their 1999 hit “I Want It That Way,” with Drake joining the group for a singalong. (It might seem a bit random, but Drizzy has previously performed with the group.) Amid all the festivities, the rapper also offered a sentimental toast. “Tonight is not about a tour or an album release or a bunch of videos that we shot or a fragrance or a Nike shoe,” he told his guests. “Tonight is just about being alive, staying alive.”

One outfit—and one party—was never going to suffice. For the second round of celebrations on Saturday evening, Drake traded his debonair tuxedo for a cheetah-print Chrome Hearts jacket and bright red leather trousers. A look all the better suited to taking the stage for a performance of his own, where he was also joined by Popcaan.

The fashion double act perfectly fit the rhythm of a musician whose personal style has become increasingly eclectic, oscillating between oversized sportswear, collegiate staples, rare archival finds, and extraordinarily expensive accessories. At 40, Drake clearly has no intention of toning things down. The weekend was, surely, the best he ever had.