Jeff Ross Roasts Drake at Surprise 40Th Birthday Bash in Houston

WHO:

AllHipHop - Drake celebrated his 40th birthday in Houston.

AllHipHop - Comedian Jeff Ross surprised Drake with a roast.

Billboard - Drake had previously requested a birthday roast from Jim Carrey.

CNN - Drake’s stylist, Juliet Charlotte, confirmed she created his birthday outfits.

CNN - Drake wore a portrait of his parents in a custom Anomaly Relic necklace gifted to him by Juliet Charlotte.

WHAT:

AllHipHop - Drake’s birthday celebrations continued with a surprise roast by Jeff Ross.

Billboard - Ross’s roast was described in the headline with the phrase “The F–king General.”

CNN - Drake appeared in a series of elaborate birthday outfits, including a big brown poncho, a custom Chrome Hearts faux-fur leopard-print jacket emblazoned with red crosses, a flowy white dress shirt, matching slick red leather pants, and burgundy cowboy boots.

CNN - The Cut dubbed Drake’s brown poncho look “Christian Girl Autumn.”

CNN - Drake’s poncho look went viral and generated Halloween costume inspiration in less than a day.

CNN - Drake reportedly booked the Backstreet Boys for a private performance at Cipriani in New York and gave guests $1 million during his birthday party.

CNN - Drake released a three-part album in 2026 and signaled he would tour next year, but had not announced tour dates.

WHERE:

AllHipHop - The roast took place in Houston.

CNN - Drake reportedly held a birthday party at Cipriani in New York.

WHEN:

CNN - Drake turned 40 on Saturday.

WHY:

AllHipHop - Drake had wished to be roasted by Jim Carrey for his birthday.

CNN - CNN characterized Drake’s birthday outfits as seemingly signaling “new decade, new Drake.”

HOW:

AllHipHop - Jeff Ross surprised Drake with the roast.

CNN - Drake’s stylist assembled his birthday outfits; the custom necklace containing the portrait of Drake’s parents was a gift from her.

(UPDATED October 29, 2026 10:02 UTC)

Drake celebrated his 40th birthday in Houston, where comedian Jeff Ross surprised him with a roast after Drake had previously asked Jim Carrey to roast him. His stylist, Juliet Charlotte, created a series of elaborate outfits, including a brown poncho that went viral and inspired Halloween costumes, and gifted him a custom necklace featuring a portrait of his parents. Drake also reportedly hosted a party at New York’s Cipriani with a private Backstreet Boys performance and gave guests $1 million; he has signaled plans to tour next year but has not announced dates.