John Oliver roasts Trump over Freedom 250 concert cancellations

Brendan Morrow, USA TODAYMon, June 1, 2026 at 1:39 PM UTC

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As artists bail on the Great American State Fair, John Oliver is reveling in schadenfreude.

The comedian began the May 31 episode of HBO's "Last Week Tonight" by poking fun at the news that the "first wave" of performers were announced for The Great American State Fair, a 16-day event on the National Mall organized by President Donald Trump-backed Freedom 250, only for multiple artists to back out.

Oliver first joked about the initial lineup, which included artists like Martina McBride, Milli Vanilli, Vanilla Ice and Bret Michaels, being subpar.

"It is a stacked lineup of people that you haven't thought about since 2009," Oliver quipped. "Honestly, that sounds less like America's 250th birthday and more like the playlist at Rhonda's 50th. The only really surprising thing about that lineup is that there's not a special appearance from the ShamWow guy and the Gushers kid whose head turned into a raspberry."

John Oliver hosts "Last Week Tonight" on HBO.

Since the lineup announcement, numerous performers have dropped out of the event, including Michaels, Milli Vanilli and Young MC. Several of the artists said they were under the impression the event, scheduled to run from June 25 through July 10, was non-partisan. "The artists were never told about any political involvement with the event," Young MC said in a Facebook post.

John Oliver jokes about future of 'Last Week Tonight' at charity event

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"That is a lot of cancellations," Oliver said on "Last Week Tonight." "Though I do have to tell you, Vanilla Ice did not pull out, which I do realize sounds like the answer to the question, 'Why does that baby have frosted tips?'"

Oliver also poked fun at some of the other events scheduled for the Great American State Fair, including screenings of the movies "National Treasure" and "National Treasure: Book of Secrets." The late-night host joked this is "bringing a real 'substitute history teacher… energy to the proceedings.

"Given how everything's been going, I wouldn't be remotely surprised if tomorrow we got a press release reading, 'Due to divisive politics, I will no longer be attending the 250th celebration' from the … ferris wheel."

In a May 30 social media post, Trump suggested the event should be canceled, writing that "we should have a giant MAKE AMERICA GREAT AGAIN RALLY" instead of performances from "overpriced singers, who nobody wants to hear, whose music is boring, and yet who do nothing but complain."

Contributing: Saman Shafiq and Mike Snider, USA TODAY

This article originally appeared on USA TODAY: Freedom 250 concert – John Oliver mocks cancellations, roasts Trump

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