On Sunday’s Last Week Tonight, John Oliver shifted his comedic sights from politics to pop culture, skewering actor Dean Cain after he announced he would be joining ICE.
Hollywood to ICE
“You know, there’s an old saying in Hollywood: ‘If all you can get is Dean Cain, you are f—ed,’” Oliver said, launching into a rundown of Cain’s filmography, including The Dog Who Saved Christmas and its many sequels. “Maybe you’re in trouble when you’re pinning a badge on the 59-year-old star of that series. On the plus side, no need for that guy to wear a mask because the chances of anyone recognizing him are f—ing zero.”
Oliver added, “In some cases, you might be unable to stop yourself from saying: ‘Didn’t you used to be Superman? I thought you died. I can’t believe I’m meeting a filmmaker.’”
Broader Critique of ICE and Trump
Oliver tied Cain’s announcement to a report from The Atlantic that ICE agents are being reassigned from serious crimes like human trafficking to low-level deportations. “For a guy who pandered so heavily to people convinced pedophiles, sex offenders, and traffickers had infiltrated our government, Trump’s sure making the government a lot friendlier to them,” Oliver said, citing examples like Ghislaine Maxwell’s improved prison conditions.
He even joked, “At this point, if he’s willing to wear a MAGA hat, I don’t see why Roman Polanski can’t come back.”
Government Messaging Misfires
Oliver also called out official government social media pages promoting aggressive deportation tactics, including one depicting Border Patrol’s Premier Sector as Darth Vader. The Department of Homeland Security’s response — noting that Darth Vader was also Anakin Skywalker — drew loud laughs from Oliver’s audience. He called it “an incredible, deeply sh—y response” and joked about wanting their take on Marvel villain Thanos.
Why It Resonates
By weaving Cain’s improbable career turn into a larger discussion of immigration policy and government messaging, Oliver blended sharp political critique with biting pop culture humor — a hallmark of his late-night style.
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