Bill Maher Addressed Touring Musicians and the Shutdown

As has often been the case on this season of Real Time With Bill Maher, a busy news week gave the show’s host and guests plenty to discuss. Maher brought up the ongoing government shutdown in his monologue, discussing the shutdown’s growing effects on air travel.

“The good news is, if the airports are shut on Thanksgiving, you won’t have to see your family,” Maher said. And then the episode’s first guest showed up, opening the door for a very different discussion of travel — the kind undertaken by touring musicians. That first guest was country musician Kenny Chensey, there to discuss his career and his recent book Heart Life Music.

“I’ve been on the road since 1993,” Chesney said. He hearkened back to that point early in his career, during a period when promoters would conflate him with Mark Chesnutt — possibly out of confusion, or possibly to sell more tickets. Maher mentioned finding parallels between those parts of the book and his own early career as a comedian.

The high point of the conversation came when both recalled their early homes.“My coffee table was a cooler. I had a secondhand couch and a secondhand bed for a while, and all I was doing was writing songs,” Chesney recalled. “That’s probably the happiest I’ve ever been in my life.” Maher recalled a similar arrangement: “My bookshelf was cinder blocks and boards that I found.” “You had your brain, though,” Chesney said.

There was another way that the two men found common ground: neither of them has children. “I’ve never woken up and thought that I was missing something,” Chensey said.

Their conversation also grew meta at times. Maher at one point said of his conversation partner, “You’re like the Sinatra of country music.” He revealed that he’s developed a growing affinity for country music. “A lot of these songs could be done by pop artists,” he said.

Chesney addressed his own musical evolution, for which he credits his time in the U.S. Virgin Islands. He spoke of “a circle of family down there that was very different” from him in terms of their beliefs and backgrounds. He then told a story about recording with longtime Wailers member Aston “Family Man” Barrett, the conversations they had about music and the common ground they found.

Maher also spoke highly of the lyrical elements of Chesney’s preferred genre. “You can’t have shitty lyrics in country or rap,” he said. Chesney was more pragmatic. “You can,” he said. “They’re there.”

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Florida Representative Jared Moskowitz and television host Bill O’Reilly joined Maher to discuss the off-year elections and inflation. Early on, O’Reilly gave a salient example of the latter. “The place where I’m staying in LA, the cheeseburger is $36,” he said. “I can buy the cow for $36.” (He clarified that he did not partake of this particular burger, instead going to In-N-Out. Moskowitz also discussed inflation, saying, “You can tell people things are great, but when they go to the store, they see that’s not the case.”

Maher also brought up how the wealth gap is growing. “When you’re 30 years old and you still have roommates — yes, capitalism has failed you,” he said. That led to a discussion of New York City mayor-elect Zohran Mamdani and his popularity. O’Reilly accused him of being a communist, an accusation based around a single comment from 2021.

Moskowitz complicated the discussion, raising a question about the Trump administration’s behavior. “While you’re talking about ‘seizing the means of production,’ Trump did take a 10% stake in Intel,” he said.

Maher and O’Reilly’s verbal skirmishes continued through much of the conversation, including the two men taking jabs at one another’s ratings. Lest anyone miss the subtext here, Moskowitz offered to produce a tape measure.

The episode closed out on a sobering note, with Maher pointing out the contrast between how the Supreme Court has treated the Biden and Trump presidencies. He pointed to the tariff case before the Court as especially significant. Or, as he put it, “Utterly ignoring the Constitution is a price too high.”

Other notable moments from this week’s episode:

Maher on the death of Dick Cheney: “Trump and Cheney, they’re very different kinds of Republicans. Cheney used to send troops to occupy other countries.”
Maher again indicated that he’d really like Zohran Mamdani to appear on the show.
O’Reilly got some of the bigger laughs this episode by comparing Andrew Cuomo to Bela Lugosi.
That said, between O’Reilly and Louis C.K., this fall’s guests have included a non-zero number of guys with unpleasant histories related to sexual harassment.

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Tobias Carroll

Tobias Carroll lives and writes in New York City, and has been covering a wide variety of subjects — including (but not limited to) books, soccer and drinks — for many years. His writing has been published by the likes of the Los Angeles Times, Pitchfork, Literary Hub, Vulture, Punch, the New York Times and Men’s Journal. At InsideHook, he has…