As late-night hosts knee-deep in coverage of the 2016 presidential campaign, Stephen Colbert and John Oliver have both had to figure out how to cover Donald Trump. Oliver recently dedicated a large segment of his weekly monologue to a Trump takedown, even creating the hashtag #MakeDonaldDrumpfAgain in order to, in his words, “separate the mascot of ‘Donald Trump’ from the man.” In a discussion on his Monday show, Colbert asked Oliver why he decided to go that route after declaring on Colbert’s show in October that he didn’t care about Trump.
“We were not in the election year, at that point,” Oliver said. “I didn’t care, and I didn’t think I’d have to care. None of us thought we were gonna be here, but we are.”
To match Trump’s ubiquitous “Make America Great Again” caps, Oliver’s team made their own hats for the “Make Donald Drumpf Again” campaign. And of the 35,000 hats sold, Oliver’s team fielded one particularly unexpected request.
“Apparently Jay Z’s people called HBO asking for a hat,” Oliver said. “I’ll say this for a start: buy the hat, Jay Z. Jay Z wanted one for free. He’s done very well — spring for a hat. Let it trickle down. That’s how economics works, right?”
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Oliver’s Drumpf hats were so in demand he had to bring one to Colbert’s show because they were unavailable otherwise, but the Last Week Tonight host said he hadn’t even seen one of the hats in real life before. This is part of why he urged caution when HBO asked if they could send Jay Z a hat.
“I did say, ‘Well, be careful, because if he puts that on in public, you’re gonna need more hats,'” Oliver said. “And if his wife puts it on in public, we are no longer a TV show, we’re a hat-manufacturing company.”
Watch the full clip below.