15 Woke Hollywood Celebrities Who Hobnobbed, Vacationed, Promoted Movies in Communist Cuba

Cristobal Herrera; Ramon Espinosa; Mayangdi Inzaulgarat; Jose Goitia/AP Photo/TBS/Joe Raed
Cristobal Herrera; Ramon Espinosa; Mayangdi Inzaulgarat; Jose Goitia/AP Photo/TBS/Joe Raedle; Jorge Rey/Getty Images

On Sunday, thousands of Cubans took to the streets to demand an end to the 62-year-old communist regime, chanting, “Down with the dictatorship,” and “We want liberty,” while waving American flags. Cuban President Miguel Díaz-Canel — the face of the Castro communist regime — responded to the protests by announcing an “order of combat” against peaceful pro-democracy protesters, urging communist civilians to assault them.

Over the years there’s been no shortage of woke left-wing celebrities who have pushed Democrat policies and have also visited, vacationed, or promoted a film or their music in Communist Cuba — normalizing and spending their money in a country with a government that controls the flow of money, as well as brutalizes and murders its own people.

Here’s a list of 15 of those woke Hollywood celebrities.

1. and 2. Jay-Z and Beyonce

This April 4, 2013 file photo shows married musicians Beyonce, left, and rapper Jay-Z as they tour Old Havana, Cuba. Jay-Z is addressing his recent trip to Cuba in a new song. The rapper released “Open Letter” Thursday, April 11, after two Florida Republicans questioned if the rapper’s visit to Havana with wife Beyonce was officially licensed. (AP Photo/Ramon Espinosa, file)

Rapper Jay-Z and his wife Beyonce are among America’s most woke left-wing activist couples. The yacht and jet-setting rap mogul-pop star couple backed Hillary Clinton in 2016, have donated millions to Black Lives Matter, spent years stoking anti-police sentiment, and reportedly helped bail out Ferguson protesters amid the riots over Michael Brown’s death.

The couple made headlines when they vacationed in Cuba in 2013, despite an economic embargo. One year earlier, political arrests in Cuba jumped to more than 6,600 — the highest it had been in decades, according to a report by USA Today.

3. Rihanna

In this May 29, 2015, file photo, fans take photographs of pop artist Rihanna, wearing a green scarf, as she is transported in an American classic car, after a photo shoot with photographer Annie Leibovitz at a building on the Malecon, in Havana, Cuba. This October’s Vanity Fair has Rihanna on the cover in Havana as celebreties keep flocking to Havana. Mick Jagger and Katy Perry have partied (separately) here over the last week. Mexico City’s hottest chef is scoping sites for a Havana restaurant. Usher and Ludacris have shown up. Jimmy Buffet’s played a private backyard concert for friends. (AP Photo/Desmond Boylan, File)

Pop superstar Rihanna — who has accused the United States Border Patrol of “terrorism” for using tear gas to stop illegal migration — visited Old Havana, Cuba, in 2015, so that she could participate in a photoshoot for a Vanity Fair cover.

That year, Cuba’s communist government issued a demolition order for every church in the Abel Santamaria district in the southern city of Santiago de Cuba.

4. Katy Perry

Meanwhile, pop star Katy Perry also visited Cuba in 2015, writing in an Instagram post that the communist country has “one of the COOLEST vibes alive,” and that its streets — filled with poverty-stricken citizens — is great for some fun photo opportunities.

“After seeing most of the world this is one of the COOLEST vibes alive,” Perry wrote. “If you like taking pictures, everything there will fit in a frame.”

“It’s a Disneyland for creatives minds,” added the singer, who encouraged her followers to “go there before it changes.”

Last year, Perry and fellow pop stars Pink, Billie Eilish, and the group formerly known as the Dixie Chicks, teamed up with Planned Parenthood for an abortion-themed ad campaign to push voter turnout in battleground states ahead of the 2020 election.

5. Steven Spielberg

Cuban President Fidel Castro (R) and movie director Steven Spielberg (L) greet residents outside cigar manufacturer Partagas November 6, 2002, in Havana, Cuba. (Jorge Rey/Getty Images)

In 2002, Hollywood director Steven Spielberg — who has donated millions of dollars to Democrats — was slammed for visiting Cuba, where he met with Cuban communist leader Fidel Castro.

In 2004, CBS reported actor Robert Duvall called out Spielberg over his visit to Cuba, saying, “Now, what I want to ask him — and I know he’s going to get pissed off — ‘Would you consider building a little annex on the holocaust museum or at least across the street to honor the dead Cubans that Castro killed?'”

“That’s very presumptuous of him to go there — I’ll tell him that,” Duvall added. “I’ll never work at Dreamworks again, but I don’t care about working there anyway.”

6. Mick Jagger

Mick Jagger, Charlie Watts, Keith Richards and Ronnie Wood of the Rolling Stones wave as they exit their plane after landing at the Jose Marti International Airport on March 24, 2016 in Havana, Cuba. The Rollling Stones are in Havana to play a free concert for the first time, after the music was once banned by the Cuban government. (Joe Raedle/Getty Images)

Rocker and Rolling Stones front man Mick Jagger — who has mocked people who chose not to get the coronavirus vaccine by comparing them to flat Earthers — was spotted in 2015 partying in Havana, Cuba, where he “showed off his dance moves,” according to a report by The Daily Mirror.

That following year, the Rolling Stones announced they would play a free concert in Cuba, where the government has been known to persecute people for listening to rock music, as it has been viewed as a tool of Western capitalism, reports CBS.

7. and 8. Ludacris and Usher

In 2015, rapper and actor Ludacris visited Cuba with singer Usher for his birthday — a trip that the rapper called his “Best Bday Ever.”

Ludacris — who joined forces with the Joe Biden presidential campaign last year — also posted a photo of himself smoking a cigar, along with the hashtag, “Havana Heaven.”

But Usher, on the other hand, appears to have deleted his Instagram posts from that 2015 trip to Cuba.

9. Conan O’Brien

Cuba appeared to be a destination hot spot in 2015, as anti-Trump late-night host Conan O’Brien also paid a visit that year.

But instead of simply using the communist country as a playground for Instagram photo opportunities, O’Brien spent several days shooting an episode of his now canceled late-night TBS show, where he was seen dancing in the streets of Havana in a white suit.

Watch below:

10. Sean Penn

In this Oct. 25, 2009 photo made available Tuesday, Oct. 27, 2009, US actor Sean Penn visits Isla de la Juventud, Cuba. Penn is in Cuba reporting for Vanity Fair magazine. (AP Photo/Mayangdi Inzaulgarat, Cubadebate)

Left-wing actor Sean Penn — who bizarrely declared earlier this year that the Pope should “impeach” evangelical leaders who fail to denounce former President Donald Trump — flew to Cuba in 2008 to interview Castro, who he later described as having the “agility of a young man” adding he “exercises every day, his eyes are bright and his voice is strong.”

The actor flew to Cuba once again in 2009 to interview Castro.

11. Kevin Costner

Actor Kevin Costner, center, in Cuba to promote his film “Thirteen Days,” shakes hands with Cuban leader Fidel Castro Tuesday April 10, 2001, in Havana, Cuba. At the left Costner’s girlfriend Christine Baumgartner. (AP Photo/Jose Goitia)

Actor Kevin Costner — who last year proclaimed that President Trump is a “criminal” who “spits on 200 years of freedom” — visited the communist country known for brutalizing its own people in 2001.

Costner had dinner and a late-night movie with Castro at the Palace of the Revolution in Havana, Cuba, where the two watched the 2000 film Thirteen Days — of which Costner is the star — about the Cuban missile crisis, according to a report by Los Angeles Times.

12. Robert Redford

U.S. film director and actor Robert Redford leaves the Cuban Institute of Film and Art Sunday, Jan. 25, 2004, in Havana, Cuba after the presentation of his new film about Che Guevara, ‘The Motorcycle Diaries,’ to the widow and children of the legendary guerrilla fighter. (AP Photo/Cristobal Herrera)

Actor-director Robert Redford — who last year praised coronavirus lockdowns and has accused President Trump of launching a “dictator-like attack” — visited Cuba in 2004 for the premier of The Motorcycle Diaries, his film about Marxist revolutionary and assassin Che Guevara.

The Motorcycle Diaries had received “the seal of approval” from Guevara’s surviving family, according to a report by The Guardian. While visiting Havana, the director also met with Castro.

13. Danny Glover

U.S. actor Danny Glover, center, attends a rally honoring Fidel Castro at the Revolution Plaza in Havana, Cuba, Tuesday, Nov. 29, 2016. Schools and government offices were closed Tuesday for a second day of homage to Fidel Castro, with the day ending in a rally on the wide plaza where the Cuban leader delivered fiery speeches to mammoth crowds in the years after he seized power. Fidel Castro passed away Friday Nov. 25. He was 90. (AP Photo/Ricardo Mazalan)

Longtime screen legend Danny Glover — who last year declared that the police in America represent the “last line of defense for white supremacy” — has spent years visiting Castro in Cuba, where the brutal communist regime reigns.

14. Harry Belafonte

Colombian writer Gabriel Garcia Marquez, left, poses with actor Harry Belafonte during the inauguration of the 24th Festival of Latin American Cinema at the Karl Marx theater in Havana, Cuba, Tuesday, Dec. 3, 2002. (AP Photo/Cristobal Herrera)

Singer Harry Belafonte — who endorsed socialist senator Bernie Sanders (I-VT) in the 2016 presidential election — has visited Cuba on more than one occasion, and has described Castro’s murderous rise to power on the island as “very heroic.”

“I thought he was a whiz,” Belafonte added of Castro. “I saw in him a lot of heroics in the very beginning that was very, very attractive.”

15. Oliver Stone

Director Oliver Stone, left, and Cuban leader Fidel Castro are seen Thursday, Feb. 21, 2002 after wrapping up shooting of a documentary in Ernest Hemingway’s preferred bar “La Terraza” in Cojimar near Havana, Cuba. The producer and others involved in Stone’s documentary on Castro have agreed to pay the U.S. government more than $6,000 to resolve allegations that they violated a longstanding embargo against the communist country in documents dated Dec. 1, 2006. (AP Photo)

Director Oliver Stone — who last year proclaimed the U.S. is an “evil empire” — visited Cuba in 2003 to interview Castro for his documentary, Comandante, which ended up facing heavy backlash from Cuban-Americans, who successfully forced HBO to pull its U.S. screening.

Stone — whose production company was later fined $6,322.20 by the U.S. government for illegally traveling to Cuba — has also described the communist leader as a “very selfless” and “moral” man who will be remembered as “one of the world’s wisest men.”

You can follow Alana Mastrangelo on Facebook and Twitter at @ARmastrangelo, and on Instagram.


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