Late Night Last Week: Trump’s Anti-Trans Bigotry, Conner O’Malley’s Return, and More

By Will DiGravio  |  February 3, 2025 | 2:30pm
TV Features late night
Late Night Last Week: Trump’s Anti-Trans Bigotry, Conner O’Malley’s Return, and More
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Every week,  ​​​​Late Night Last Week highlights some of the best late night TV from the previous week. This week, Michael Kosta and The Daily Show look at Trump’s anti-trans dictates, Conner O’Malley and Pittsburgh Pirates phenom Paul Skenes talk to Seth Meyers, and Taylor Tomlinson fails to muster up any interest in AI.

Daily Show correspondent Michael Kosta was in the host’s chair last week, making use of his conservative-bro-adjacent persona to tackle the endless stream of news coming from the new presidential administration. As part of his monologue, Kosta tackled the Trump administration’s new military strategy, including “our country’s month-old dream of conquering Greenland.” Kosta then pivoted to an executive order Trump signed banning transgender soldiers from serving. 

“Look, I don’t have a problem with transgender soldiers. As someone who pees himself any time he hears a loud noise, I think we should be grateful to anyone who’s put their life on the line so I don’t have to,” Kosta said. “But, I’m open-minded about being close-minded. So what’s the issue?” 

Kosta then went on to play a montage of news segments summarizing the executive order, pointing out the language stating that transgender service members are not adhering to the military’s commitment to being “honorable,” “truthful,” and “disciplined.” “I gotta say, the military sure has a lot of ethical rules for its mission of killing people,” Kosta observed.

As the segment continued, Kosta went on to expose another of the reasons given for the ban: recovery times after surgery. “Do you know how long our wars last?” Kosta asked. “Vietnam War? 11 years. Afghanistan War? 20 years. Even our Storage Wars last 15 seasons.” 

Another big bit of recent news relates to the world of artificial intelligence, the topic some people really care about and everyone has to at least pretend to care about. Such was the subject of Taylor Tomlinson’s After Midnight monologue on Tuesday, January 28. She came out sharing the news that the Chinese app DeepSeek has threatened US supremacy in AI, doing practically the same thing as ChatGPT but for a fraction of the price. 

“I can feel everyone in here, including me, not giving a shit,” Tomlinson said, holding back laughs after playing a clip of a TikToker reacting to sinking stock prices. “For the people at home, I have no idea how this feels to you. I can tell you, in here, we do not care at all.” The crowd cheered. “I had to have our monologue writers explain this shit to me,” Tomlinson added. 

Conner O’Malley, whose appearance on Late Night with Seth Meyers last year featured in our round-up of the best in late night, returned to the program on Thursday. The ex-Late Night writer and performer is currently on tour (I saw him the night before his appearance in Burlington, Vermont, where he killed), bringing to the stage a mix of in-character stand-up and screening his latest video work. O’Malley on Meyers is always a must watch. 

“Seth fired me,” he quickly informed the audience. “Seth fired me because of my political beliefs. Seth was really upset I supported Republic-ism in Ireland.” This led to another trip down memory lane. O’Malley recounted how Meyers would behave each night when getting his make-up done: “You would look at the make-up artist and you would just go, ‘Can you believe how nice I’m being to ya?’” 

Keeping with Meyers for a moment: One of the biggest stories in sports as of late has to do with baseball cards. Stay with me. Last season, Topps, the most storied producer of baseball cards, tried something new. They had rookie players wear a patch on their uniforms marking their MLB debut. These patches were then cut from their jerseys and placed in 1/1, signed rookie cards. The crown jewel of this series was a card featuring Pittsburgh Pirates ace Paul Skenes. The team itself offered whoever pulled the card an insane trade package, including two seats behind home plate for every game for 30 years. 

Well, the card was finally pulled in a pack last month by an 11-year-old collector in Los Angeles. It is now headed to auction. Last week, Skenes appeared on Meyers where he was asked about the news, and specifically about the card going to a kid. “What would have been the worst outcome for you?” Meyers asked of the chase for the card. Skenes didn’t hold back: “Probably … probably a 50-year-old collector, to be honest.” 

Meyers and Skenes also discussed their respective appearances on Garbage Pail Kids cards. Skenes was featured as “Parroted Paul” and Meyers as “Smart Aleck Seth.” Meyers then signed one for Skenes. “I feel like nobody ever signs anything for you,” Meyers said. 

Finally, we end with Jon Stewart. On the Monday episode of The Daily Show, the host interviewed firefighter Royal Ramey, CEO and co-founder of the Forestry and Fire Recruitment Program, which helps formerly incarcerated persons become firefighters. Ramey and Stewart discussed the prison-to-public-service pipeline, and how working as a firefighter while incarcerated offers some of the best conditions and wages: about $1 an hour, Ramey said, further highlighting, as Stewart pointed out, just how horrible the system is to begin with. “Here’s where it gets ugly for liberals,” Stewart said. 

But the conversation did turn towards the positive, with Ramey explaining the benefits and opportunities the program affords. “A lot of folks can’t even fathom having a career, just having that felony on your record,” Ramey said, adding that the program is one of the best rehabilitations offered in the state, “to being able to possibly have a six-figure career, benefits, retirements, and be able to take care of your family for a long time.” 

Stewart and Ramey also discussed the ludicrous rules regarding becoming a certified firefighter once one’s time in prison ends. Ramey explained that additional paperwork and certifications are needed. “You’re already doing the job,” an incredulous Stewart said. “But they’re saying to you, yes, you can fight the fires, but you’re not qualified to fight the fires.” 

Will DiGravio is a Brooklyn-based critic, researcher, and late night comedy columnist, who first contributed to Paste in 2022. He is an assistant editor at Cineaste, a GALECA member, and since 2019 has hosted The Video Essay Podcast. You can follow and/or unfollow him on Twitter and learn more about him via his website.

 
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