The Stones started their first-ever show in Cuba with Jumpin' Jack Flash, a song recorded in 1968, when Cuban rock fans were secretly sharing pirated vinyl records and risked being sent to rural work brigades to cure "ideological deviation".
"We know that years back it was hard to hear our music in Cuba, but here we are playing. I also think the times are changing," lead singer Mick Jagger said in Spanish to a roar from the crowd.
The singer spoke in Spanish throughout of the 18-song show of hits that lasted more than two hours. The band played Sympathy for the Devil as a yellow moon rose through clouds, and they finished a two-song encore with Satisfaction.
Fans started gathering 18 hours ahead of time at Havana's Sports City football and baseball fields, including Cubans who travelled from across the Caribbean's largest island and foreigners who flew in for the occasion.
While no official estimate was immediately available for the crowd size, Cuban state media estimated half a million people could fit in the venue, which was nearly full.
The audience ranged from teenagers to pensioners and reserved some of the biggest cheers for Jagger's snakey dance moves.
"I love Mick Jagger so much. I've always dreamed about this. I couldn't sleep knowing he would be here," said Angela Menendez, who cleans floors in a hospital.
Security was low key and there was a noticeable absence of would-be entrepreneurs selling T-shirts or memorabilia.
People were dressed in all manner of jeans, T-shirts and boots with the Stones' tongue and lips logo.
Cubans have taken to colouring the tongue with the stars and stripes of the United States flag, whether in the mistaken belief that the British rock stars were American or in the spirit of this week's historic visit by United States President Barack Obama.
The Stones formed in London in 1962, three years after Fidel Castro's bearded rebels toppled a pro-American government.
Castro's revolutionary government came to see counterculture bands like the Stones and the Beatles as dangerously subversive and prohibited their music on TV and radio.
Half a century later, both the Rolling Stones and Cuba's leadership share a longevity, performing well beyond what most people would consider retirement age.
The band's advancing years did not stop the youngsters in the audience enjoying the show, however.
"Don't let anybody tell you different, this is the best concert in the history of Cuba," said Cristian, 18, a reggaeton fan who this month saw electronic music act Major Lazer in another free gig.
For Juan Carlos Leon, 57, the event was more than special.
"To me, this is a consecration," Leon said. "I've waited my whole life for this. The Stones are the greatest."
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