Go Inside Madonna’s Three-Day Cuban Birthday Extravaganza with Steven Klein and Rosie O’Donnell

What do you do when you’re the queen of pop on your 58th birthday? Charter a plane and fly your friends and family to Havana for a dance party and tres leches cake, of course.


On this day, August 16, 1958, our lady Madonna was born. She turned 58 Tuesday, to much fanfare and Instagramming — and, of course, with a blowout celebration to match. On Monday evening, Madonna and her closest friends and family, including daughter Lourdes Leon and sons Rocco and David Banda Ritchie, chartered a jet and set a course for Havana, Cuba, for a three-day blowout of eating, dancing, and joyriding in vintage cars.

Upon her arrival in Cuba, the birthday girl posted a series of selfies just before heading out for the first night of celebrations. Her birthday look wouldn’t be complete without the full beauty squad she brought along for the ride, including makeup artist Aaron Smith Henrikson, who has been doing his share of posting the festivities, and hair stylist Andy LeCompte.

She and her cohort then headed to Cuba’s historic district for dinner — and, more importantly, dancing, accompanied by a live band and cries of, “We in Cuba, baby!”

Before they even touched down in Cuba, though, actress Debi Mazar was already posting selfies from inside the plane, surrounded by the paper wheels and stars hanging from the cabin ceiling. “Haven’t been back to Cuba in 20 yrs!” she captioned. (She and Madge’s squad are just the latest in a series of celebrities to take advantage of the newly lifted travel restrictions between the United States and Cuba; Beyoncé and Jay Z visited in 2013, shortly before the embargo was lifted, while Karl Lagerfeld’s Cruise 2017 show for Chanel took place in the streets of Havana this May.)

Mazar was joined by Madonna’s long-time friend, comedian Rosie O’Donnell, upon landing; they rode in a fleet of vintage ’50s cars from the airport into the city. (If the twin-C stamps on the windshields are any indicator, these are the same Chevys that shepherded Karl Lagerfeld and company around Havana for the Cruise show.) Also among the crowd celebrating nearly 60 years of Madonna were photographer Steven Klein, stylist B. Akerlund and her husband, Swedish musician and director Jonas Akerlund (also Instagramming up a storm), and Loic Mabanza, one of Madonna’s dancers and collaborators.

Local paper Granma reported Monday that the gang is sticking around in Havana till Wednesday, taking full advantage of the getaway. Can you believe we’re coming up on nearly 60 years of Madonna?