Fidel Castro, the former communist dictator of Cuba, met with many famous Americans over the years.

• Karen Bass (current Los Angeles Mayor ): has visited Cuba multiple times. She has a history of supporting the Cuban regime and even volunteered with the Venceremos Brigade organized by Fidel Castro in 1969.
• Oliver Stone: The film director visited Castro multiple times and even made a documentary about him called “Comandante”.
• Jack Nicholson: The actor visited Cuba in 1998 and had a memorable meeting with Castro.
• Kevin Costner: The actor went to Cuba in 2001 to give Castro a private screening of his movie “Thirteen Days”.
• Naomi Campbell: The model met Castro in 1999 and was quite impressed by him.
• Robert Redford: The actor and director met Castro more than once, including a scuba-diving trip.
• Beyoncé and Jay-Z: The celebrity couple visited Cuba in 2013 for their fifth wedding anniversary.
• Mick Jagger: The Rolling Stones frontman performed in Havana in 2016, marking a historic event.
• Muhammad Ali: The legendary boxer visited Cuba in 1996 and met with Fidel Castro. It was a significant moment, given Ali’s status as a global icon.
• Jimmy Carter: The former U.S. President visited Cuba in 2002, becoming the first sitting or former U.S. president to do so since the Cuban Revolution. He gave a historic speech at the University of Havana, calling for improved U.S.-Cuba relations.
• Sean Penn: The actor visited Cuba in 2009 and met with Castro. His visit sparked a lot of media attention and debate.
• Ted Turner: The media mogul and founder of CNN visited Castro in the early 1990s.
• Francis Ford Coppola: The acclaimed director met with Castro while visiting Cuba.
• Alice Walker: The author of “The Color Purple” visited Cuba and met Castro as well.
• Harry Belafonte: The famous singer and actor visited Cuba and had a close relationship with Castro.
• Jane Fonda: The actress and political activist visited Cuba and met with Castro in the 1980s.
• Danny Glover: The actor and activist visited Cuba and met with Castro in 2009.
• Angela Davis: The political activist and scholar visited Cuba multiple times and had a strong connection with Castro and the Cuban government.
• Chris Dodd: The former U.S. Senator met with Castro during a congressional delegation visit to Cuba.
• Elijah Cummings: The former U.S. Representative visited Cuba and met with Castro in 2000.
• Jesse Jackson: The civil rights leader and politician met with Castro in the 1980s and 1990s, working on diplomatic missions.

And of course, the Clintons had an encounter with Fidel Castro. During the United Nations Millennium Summit in September 2000, President Bill Clinton and Castro shook hands and exchanged a few words. This handshake was significant as it was the first time a sitting U.S. president had ever shaken hands with Castro.