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Bill Maher torches Sean Penn for Trump meeting hypocrisy: ‘You met with f–king Castro and Hugo Chavez’
Jun 16, 2025
Bill Maher torched Sean Penn for criticizing the HBO host’s meeting with President Trump – hitting back that the “Fast Times at Ridgemont High” actor had no qualms about sitting down with dictators Fidel Castro and Hugo Chavez.
During an episode of Maher’s “Club Random” podcast on Sunday, Penn ridiculed some of Trump’s comments, like his threat to annex Canada, as the pair smoked cigars and drank booze.
Maher interjected: “But you do, I hope, think I did the right thing to have dinner with him.”
“Absolutely, you’re so smart,” Penn quickly replied.
But Penn said he would not accept an invitation to meet with Trump if he received one, and that he wished Maher didn’t spend so much time discussing the visit on his show.
“Really, you meet with f—ing Castro and Hugo Chavez, but not the president of the United States?” Maher retorted.

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Maher shared on his show in April that he met with Trump during a dinner at the White House organized by musician Kid Rock, a close Trump ally who performed at the Republican National Convention last year.
Penn, a longtime Democratic activist, landed big-name interviews in the early 2000s with Communist leaders Raul Castro and Hugo Chavez.
Penn previously said he met with Fidel Castro, though that discussion was not made public.
He also traveled to Iran to cover the country’s elections in 2005.
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