During Argument Over Trump, Bill Maher Hits Sean Penn With The Million-Dollar Question

Posted • June 16, 2025: I don't often agree with Bill Maher, but every now and then, the left-winger manages to do a number on one of his own. That happened on Saturday evening when the comedian interviewed actor Sean Penn, and for perhaps the first time in his life, the Hollywood legend was asked the million-dollar question. To understand what I mean by that, you have to understand Penn's political background. Believe it or not, the left's obsession with undermining America and propping up its adversaries to spite Republicans didn't begin with Donald Trump. It seems quaint now, but there was a time when claiming Cuba had a better model than the United States was all the rage among celebrities, and while Penn started by rhetorically bro-hugging Fidel and Raul Castro, he eventually moved on to openly supporting communist dictator Hugo Chavez in Venezuela. Penn even went so far as to say that Americans who call Chavez a dictator should be thrown in jail.

The actor's authoritarian instincts have only grown stronger over the years. In 2022, he demanded that the "unvaccinated" be imprisoned. So yeah, Penn doesn't exactly have a problem with dictators and dictatorial dictates. But when it comes to Donald Trump, he's suddenly a beacon a moral light, standing in the gap to protect "democracy." That's a contradiction that Maher noticed and pressed during their interview when the two discussed whether Penn would go to dinner with the president. 🚨 Bill Maher SCOLDS Sean Penn for saying he *wouldn't* have dinner with TRUMP. 🚨 Penn's excuse is that he doesn't think speaking to Trump would get him anywhere, which is a bit odd, because I don't recall Chavez and Castro being famously malleable. Heck, this is a guy who met with 'El Chapo.' How much "influence" did he have over an infamous cartel leader? But Trump would be a bridge too far.

I mean, come on. We all know what this is. Penn is just a communist who enjoys the spoils of our capitalist society, cosplaying as a revolutionary along the way. He has no guiding principles. He's a fraud. He's not alone either. While Trump continues to obey court orders and act decidedly not like a "king," you've got left-wingers marching in the streets chanting "no kings." It's an absurd projection from people who have never met an unelected bureaucrat who they didn't want to control their lives. There's nothing undergirding any of this. It's just lazy, mindless opposition.

RedState: During Argument Over Trump, Bill Maher Hits Sean Penn With the Million-Dollar Question
https://redstate.com/bonchie/2025/06/16/watch-during-argument-over-trump-bill-maher-asks-sean-penn-the-million-dollar-question-n2190535
Twitchy: Sean Penn's Dictator Dinner Club: Outraged at Bill Maher's Trump Meet-Up, But Cool with Castro, Chavez
https://twitchy.com/justmindy/2025/06/16/bill-maher-sean-penn-meeting-with-trump-n2414323