Bill Maher eviscerates Sean Penn with ultimate comeback after Hollywood star calls out his dinner with Trump

Bill Maher was baffled that Hollywood star Sean Penn would question his dinner with Donald Trump after the Oscar winner had met with the likes of Cuban dictator Fidel Castro.

Penn stunned the comedian on his Club Random podcast when he said he would have not met with the president as Maher did in April. 

But in the ultimate retort, Maher turned the tables back on Penn: ‘Really? You’ll meet with f***ing Castro and Hugo Chavez, but not the President of the United States?’

Penn met with socialist Venezuelan President Hugo Chavez in 2007, in Caracas, when he was considered a villain by the Bush administration.

In 2008, President Raul Castro of Cuba granted him his first interview with a non-Cuban and at one point, he met Fidel Castro while on a trip to Havana. He also visited Iraq in 2002 and Iran in 2005.  

In 2016, he shocked the world, admitting to have met and interviewed Joaquin ‘El Chapo’ Guzmán.  

Maher was actually seeking the left-wing actor’s approval for his dinner with Trump: ‘But you do, I hope, think I did the right thing to have dinner with him.’

‘Absolutely, you’re so smart,’ replied the Fast Times at Ridgemont High star.

Bill Maher (pictured) was baffled that Hollywood star Sean Penn would question his dinner with Donald Trump after the Oscar winner had met with the likes of Cuban dictator Fidel Castro

Penn (pictured) stunned the comedian on his Club Random podcast when he said he would have not met with the president as Maher did in April

‘Look, this is the President of the United States, whether we like it or not, doesn’t matter,’ Penn continued. 

‘I think that when you talked about it on the show that I would have preferred that I saw his mission or his will to have the dinner, I wish I would have seen it as less successful. Because you’re so smart on policy.’ 

Maher retorted: ‘Well it was less successful because I never stopped saying all the things I’ve always said about him. It would have been successful if he had somehow seduced me into supporting him.’ 

That’s when Penn said he would not have done it, in part jokingly that ‘it’s a long flight’ but also suggesting there would be no purpose.

Penn responded to Maher’s crack about having met Castro and Chavez by saying he ‘saw good results come out of some of those things.’

‘I just personally wouldn’t trust anything that was said in the room,’ Penn summed up.

Maher replied: ‘It’s not a matter of trusting it, it’s a matter of seeing it, a matter of experiencing it, a matter of knowing it.’

He compared it to someone who didn’t want to get tested medically because they might not want to know something was wrong with them. Penn ultimately agreed.

Maher’s response: ‘Really? You’ll meet with f***ing Castro and Hugo Chavez, but not the President of the United States?’

In 2016, Penn (pictured left) shocked the world, admitting to have met and interviewed Joaquin ‘El Chapo’ Guzmán (pictured right) 

Unlike Castro and Chavez, Penn later expressed regret for the interview with El Chapo, saying his goal was to start a conversation about the war on drugs.

The acclaimed actor also accused the Mexican government of endangering his life by claiming that his meeting with El Chapo led to his eventual capture.

El Chapo was arrested the next year and eventually extradited to the United States, where he is on trial.

Maher said Donald Trump was ‘gracious and measured’ in what he described as a positive meeting with the president, to the point that he walked away with a cheeky gift.

Maher has always attacked Trump on his HBO show dating back over a decade, when the two were involved in a lawsuit over Maher claiming the president’s father was an orangutan. 

On Friday’s show, he took time out exclusively to ‘give you my book report on my visit to the White House,’ which saw him have dinner with Trump and UFC owner Dana White.

The lefty comedian confirmed the meeting had been arranged by musician and Trump fan Kid Rock, who also attended: ‘Because we share a belief that there’s gotta be something better than hurling insults at each other from 3,000 miles away.’

He slammed those who saw the event as some kind of important diplomacy meeting.

Bill Maher has dinner in the White House with President Donald Trump and Kid Rock

Penn later expressed regret for the interview with El Chapo, saying his goal was to start a conversation about the war on drugs

‘For all the people who treated this like it was some sort of summit meeting, you’re ridiculous. Like I was gonna sign a treaty or something? I’m a f***ing comedian, I have no power! He’s the most powerful leader in the world, I’m not the leader of anything,’ Maher said. 

The comic did say that he wanted to represent ‘a contingent of centrist-minded people who believe there’s got to be a better way of running this country than hating each other every minute.’

He confirmed that Trump was a ‘different’ person than he’d seen in the public eye over the last decade and even the night before, when the president publicly wondered if the meeting was even a good idea.

‘The guy I met is not the person who, the night before, s***-tweeted a bunch of nasty crap about how he thought this dinner was a bad idea, and what a deranged asshole I was.’ 

‘He’s much more self-aware than he lets on in public,’ Maher added. 

Perhaps most striking to Maher was that Trump ‘laughed’ and has a sense of humor about himself. 

‘First good sign, before I left for the capital, I had my staff collect and print out this list of almost 60 different insulting epithets that the president said about me,’ Maher said.

‘I brought this to the White House because I wanted him to sign it, which he did with good humor,’ he added.

Trump signed a list of insults the president had directed at Maher over the years ‘with good humor’

He joked about how the hoards of MAGA haters must be hating this: ‘I know as I say that, millions of liberal sphincters just tightened.’

‘I’m gonna report what happened and you decide. If that’s not enough pure Trump hate for you, I don’t give a f***,’ Maher said unapologetically. 

He said that the president did not ask him for his support and when he gifted Maher several Trump hats, he didn’t ask him to take a photograph wearing them.

‘I’m just taking it as a positive this person exists because everything I’ve ever not like about him was, I swear to God, absent, at least on this night with this guy,’ he said.

The discussion largely was one of Trump asking for Maher’s thoughts on various hot political topics, which he said he was heard out on, if not agreed with. 

He confronted Trump mostly that he agreed with him on several issues, like immigration, improving police morale, keeping transgender people out of women’s sports and several other ideas.  

‘I never felt I had to walk on eggshells around him,’ he said.

Maher said that while he voted for Hillary Clinton and Barack Obama, ‘I would never feel comfortable talking to them the way I was comfortable talking to Donald Trump.’

‘I feel it’s emblematic of why the Democrats are so unpopular these days,’ he said, taking shots at liberals for their ineffective means of protest against the president.

The pair even joked about the orangutan lawsuit, with Maher explaining he didn’t like how he discussed Barack Obama’s place of birth and Maher saying the president understood. 

All along, he seemed to reiterate that he wished the Trump he met would be like that all the time, asking: ‘Why can’t we get the guy I met to be the public guy?’

‘I went into the mind and that’s what’s down there. A crazy person doesn’t live in the White House. A person who plays a crazy person lives there, which I know is f***ed up, its just not as f***ed up as I thought it was,’ he said in summary. 

He said that he believes that the pair will likely go back to insulting each other, joking about Trump starting ‘a new list.’

However, he said that he believes Trump understands that ‘I have a job to do.’

‘MAGA fans, don’t worry. Your boy gave me nothing, just hats and a very generous amount of time and a willingness to accept me as a possible friend even though I’m not MAGA, which was the point of the dinner,’ he said.

However, late on, the two shared a moment in the Oval Office where both admitted that there were a lot of people who liked that they were meeting but a lot of people who didn’t want them to meet whatsoever.

It was there that they were both in complete agreement. 

‘The people who don’t even want us to talk? We don’t like you,’ he said.