John Oliver didn’t hold back while mocking Dean Cain’s decision to join ICE, unleashing a scathing monologue on Last Week Tonight. “I’m not saying that ICE isn’t finding people,” Oliver quipped. “I’m just saying, when you are reduced to pinning a badge on the 59-year-old star of The Dog Who Saved Christmas, The Dog Who Saved Christmas Vacation, The Dog Who Saved Holidays, The Dog Who Saved Halloween, The Dog Who Saved Easter and The Dog Who Saved Summer, maybe you are in trouble… On the plus side, no need for that guy to wear a mask because the chances of anyone recognizing him are f*cking zero.”

Oliver’s biting delivery lit up social media, with fans praising him for the savage pop culture takedown. But how did Dean Cain hit back after Oliver’s brutal roast? Get the full details now! 👇👇

John Oliver Roasts Dean Cain for Joining ICE, Says “No Need” for Former Superman to Wear a Mask

John Oliver took aim at actor Dean Cain during the latest episode of HBO’s Last Week Tonight, mocking the former Lois & Clark star’s announcement that he plans to join U.S. Immigration and Customs Enforcement (ICE). Oliver used the moment to poke fun at both Cain’s career trajectory and what he framed as ICE’s struggles to recruit new agents.

From Superman to ICE Recruit

Cain revealed on Jesse Watters Primetime last week that he intends to be “sworn in as an ICE agent, ASAP.” The announcement came as ICE continues to conduct high-profile raids across the country, a move that Oliver described as part of the agency’s “more than a little desperate” push for new hires. According to Oliver, ICE has relaxed age limits for recruits and released what he called “gross recruitment ads” to entice applicants.

Oliver Questions ICE’s Hiring Standards

“It shows you that maybe ICE is in trouble,” Oliver said. He then cracked, “There’s an old saying in Hollywood: if all you can get is Dean Cain, you are f—ed.”

Oliver continued by pointing to Cain’s more recent filmography, which is dominated by a string of made-for-TV family films, including six titles in The Dog Who Saved… franchise: Christmas, Christmas Vacation, Holidays, Halloween, Easter, and Summer.

No Mask Required, Says Oliver

Oliver went on to suggest that Cain wouldn’t need to conceal his identity while on duty. “On the plus side, no need for that guy to wear a mask because the chances of anyone recognizing him are f—ing zero,” he quipped.

Cain Fires Back

Cain responded on X (formerly Twitter), accusing Oliver of lifting the “mask joke” from the internet and mocking Oliver for once laughing at Donald Trump’s presidential campaign announcement. “Case closed. (And those movies were sweet, by the way!),” Cain wrote.

A Career Shift in the Spotlight

Cain, now 59, rose to fame in the 1990s as Clark Kent/Superman in ABC’s Lois & Clark: The New Adventures of Superman. In recent years, however, his work has largely been in television films, particularly holiday-themed family comedies. His decision to join ICE has sparked both praise and criticism, with supporters applauding his commitment to law enforcement and detractors questioning the move.

Oliver’s Larger Point

Oliver’s jab at Cain was part of a broader critique of ICE’s recruitment challenges and the political optics of its recent high-profile raids. By highlighting Cain’s hiring, Oliver suggested the agency might be resorting to celebrity spectacle over substantive recruitment strategy.

If you want, I can turn this into a full-length, 1000-word feature in the same detailed, bold-lead paragraph style I’ve used for your previous long pieces so it matches your earlier requests. That would let us dive deeper into Oliver’s comedic style, Cain’s career arc, ICE’s public image, and the cultural politics behind the exchange. Would you like me to expand it?