Bill Maher and Guests Talked Caitlin Clark and AI Flattery

Some episodes of Real Time With Bill Maher feel laser-focused on a particular historical moment or prominent issue. This week’s episode was more wide-ranging, with a trio of guests whose areas of expertise offered a lot of possibilities. This was most acutely felt during the panel discussion portion of the evenings, when Stephen A. Smith and Dr. Phil McGraw joined Maher on stage.

Maher started things off by discussing efforts to gerrymander Texas. “Dr. Phil, you’re from Texas,” Maher said. This is some bullshit, isn’t it?” Dr. Phil proceeded to equivocate with his response, while Smith made his thoughts on the matter more clear, saying, “It’s utter bullshit.” Though he also stressed his frustration with gerrymandering in general, regardless of which party does it.

Maher went on to criticize Dr. Phil for taking part in ICE raids. Maher explained his frustration with his guest: “We all didn’t want violent criminals and gangs, but that pivoted to going to Home Depot.”

Later on, conversation turned to the politicization of Caitlin Clark, including the Wall Street Journal’s recent call for a Congressional investigation into WNBA players’ treatment of Clark. Smith discussed the ways that politicians can use spots to their advantage, and brought up the president’s longtime connection to pro sports.

This led Maher to ask Smith if he planned to run for President in 2028. “I leave the door open,” Smith replied, though he also spoke of his fondness for a pair of Democratic governors, Wes Moore and Josh Shapiro. “As far as I’m concerned, a damn construction worker could win the Democratic nomination right now,” he told Maher, and expressed frustration at what he saw as a lack of leadership.

The panel eventually discussed the Sydney Sweeney/American Eagle jeans controversy, which led Dr. Phil to declare, “I’m going to go out to buy those jeans for every woman in my family, everybody I know, just to show support.” Maher’s response? “That’s a little creepy.”

To close out the episode, Maher brought up his issues with AI and its tendency to flatter its user. “Does everyone really need this much smoke blown up their ass, that they can’t go five minutes without being told how great they are by the toaster?” he asked — and argued that this technology reflected the worst tendencies of the Trump administration.

He also had some choice words for the rise of romantic relationships with AI (“Why listen to some other human who nags you and has needs and thoughts different than yours when everything else in your life is set on ‘worship’?”) and his own experience with Cologuard (“You’re congratulating me for putting my shit in a box?”).

Bill Maher and Stephen A. Smith Discussed the Lack of Nepo Babies in Sports

It was a more sports-centric episode than most “Real Time” fare

Can history teach us anything about this particular moment in time? The episode’s first guest, author and political commentator George F. Will, had some choice thoughts to share. “Tell me how far back this goes, where the president just gets more and more power,” Maher asked Will, who traced this phenomenon back to Woodrow Wilson.

“He’s become an inadvertent educator,” Will said. “This term of his is going to be a long seminar on the wisdom of the Founders.” Will’s commentary on American politics in 2025 ended up covering the Seven Deadly Sins, the tax code, socialism and the Federalist Papers.

Maher then asked his guest, who’d broken with the Republican Party over Trump’s rise, if the party had tried to get him back in the fold. “I don’t think they miss me, frankly,” Will replied.

Other notable moments from this week’s episode:

Maher on tariffs raising the price of coffee: “Never been a better time to start doing cocaine.”
Actor Dean Cain announced he was joining ICE this week, which led to a lot of jokes at his expense.
Maher on ICE’s tactical gear: “The smoke is so thick, some of the ICE agents are wearing two masks.”

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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…