Skip to content
Search

John Oliver Roasts Trump’s Freedom 250 Concert: ‘People You Haven’t Thought About Since 2009’

"Vanilla Ice did not pull out, which I do realize sounds like the answer to the question, 'Why does that baby have frosted tips?'"

John Oliver Roasts Trump’s Freedom 250 Concert: ‘People You Haven’t Thought About Since 2009’
Courtesy of HBO

John Oliver recounted the disaster that Donald Trump‘s upcoming Freedom 250 concert series is quickly becoming on HBO‘s Last Week Tonight. The shows, intended to celebrate America’s 250th birthday, were announced with a lineup of artists like Bret Michaels, Vanilla Ice, C+C Music Factory, and Milli Vanilli.

“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 there aren’t special appearances from the ShamWow guy and the Gushers kid whose head turned into a raspberry.”


Several of the artists, including Martina McBride and Michaels, signed on thinking the event was nonpartisan. But it has emerged that it is not.

“Now, crucially, the organization planning that event, Freedom 250, is not the same thing as the non-profit America250, led by a bipartisan board created by Congress,” Oliver recounted. “Instead, it’s a public-private partnership launched by the White House with some dicey elements, including the fact that for $1 million, donors to it could get access to Trump. And as its political slant became clear, acts who were part of that initial announcement quickly began to bail.”

Over the past week, Young MC, Morris Day and the Time, McBride, Michaels, and the Commodores have all pulled out. This led to Trump proclaiming on Truth Social that he would replace them and “give a major speech, rallying the Country forward like I have done ever since being President!”

“Yeah, that is a lot of cancellations,” Oliver acknowledged. “Although 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?’ Even some of the acts currently still scheduled to play may not be the exact people you’re expecting. For instance, neither of the C’s in C+C Music Factory will be performing, it’s just their rapper Freedom Williams, who initially agreed to perform, then considered backing out, then doubled down on performing because he was so mad that people were criticizing him.”

The late-night host continued, “Even with those cancellations, there will still be things to do, because Freedom 250 is also touting attractions that will include state and territory showcases from across America, a 110-foot Ferris wheel, CEO and innovator-led conversations and demonstrations, and special screenings of the iconic films National Treasure and National Treasure: Book of Secrets, bringing a real ‘substitute teacher doesn’t give a fuck’ energy to the proceedings.”

He added that he assumed even some of the non-human attractions would eventually cancel: “Given how everything has 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 fucking Ferris wheel.”

More Stories

Hudson Williams Takes on a New Mystery in Upcoming Series 'YAGA'

Hudson Williams and Carrie-Anne Moss in ‘Yaga.’

Christopher Lawrence/Crave

Hudson Williams Takes on a New Mystery in Upcoming Series 'YAGA'

For a guy who was still waiting tables a few months ago with dreams of breaking out as an actor, Hudson Williams must feel pretty busy these days.

The Heated Rivalry phenom stars in YAGA, a new Crave Original that makes its world premiere at the Toronto International Film Festival today, before arriving on the streaming service next October 23. The eight-episode series comes from Canadian playwright and showrunner Kat Sandler, who adapted the project from her 2019 play of the same name.

Keep ReadingShow less
Emmy Awards 2026: See the Complete Winners List

Matthew Rhys wins Outstanding Lead Actor in a Comedy Series Award for ‘Widow's Bay’ and Outstanding Lead Actor in a Limited or Anthology Series or Movie Award for ‘The Beast in Me’ at 2026 Emmy Awards.

NBC via Getty Images

Emmy Awards 2026: See the Complete Winners List

The 2026 Emmy Awards are here — and the stars have come out in full force to celebrate the best in television and accept their trophies.

This year, medical drama The Pitt led all nominees with 25, including Outstanding Drama Series, a distinction the show won last year alongside acting wins for stars Noah Wylie and Katherine LaNasa. This year, Wylie, LaNasa, Patrick Ball, Shawn Hatosy, Gerran Howell, Taylor Dearden, Fiona Dourif, and Sepideh Moafi are all nominated for their performances.

Keep ReadingShow less
Seth Rogen Honoured With Career Achievement Award at TIFF

Seth Rogen and Lauren Miller Rogen

Dan Arnold/Hilarity for Charity

Seth Rogen Honoured With Career Achievement Award at TIFF

Seth Rogen was officially welcomed into TIFF’s Canadian hall of fame Sunday night, receiving the Norman Jewison Career Achievement Award at the festival’s annual Tribute Awards.

The Vancouver-born actor, writer, producer and director was honoured for a career that has stretched from Freaks and Geeks and Superbad to Pineapple Express, The Fabelmans and the Emmy-winning Apple TV+ series The Studio. The award recognizes Canadian talent whose work has made a global impact.

Keep ReadingShow less
Dave Chappelle Is Going Back Out on the Road This Fall

Dave Chappelle in Las Vegas in 2025.

Chris Unger/TKO Worldwide LLC/Getty Images

Dave Chappelle Is Going Back Out on the Road This Fall

Dave Chappelle is heading out on tour this fall. The comedian will perform his new comedy set Karmageddon across seven dates this October and November, including a special performance the 22nd New York Comedy Festival at Madison Square Garden.

Kicking things off in Nashville on Oct. 20, Chappelle will tour across the United States and Canada, making his way through Charlotte, Toronto, and Austin, among other cities. The tour will end in New York as he opens New York’s Comedy Festival on Nov. 6 at Madison Square Garden.

Keep ReadingShow less
''We Are All Canadians'' Says Helen Mirren

Helen Mirren attends Netflix's “The Thursday Murder Club” New York Screening at The Plaza Hotel on August 14, 2025 in New York City

Arturo Holmes/WireImage

''We Are All Canadians'' Says Helen Mirren

The ongoing trade war between the United States and Canada has seeped into culture. With the Toronto International Film Festival well under way, more and more stars are using their time onstage and on the red carpet to decry Donald Trump's tariffs, comments, and his recent renaming of Lake Ontario to 'Lake America'.

British legend Dame Helen Mirren was among them. The iconic actress is in Toronto, where she received a TIFF Tribute award last night. Speaking to Radio-Canada, she expressed support to Canadians, adding that she feels like she's one of us. ''I want to defend all of Canada, French and English,'' she said. ''I wanted to print t-shirts before I came here that said 'We Are All Canadians', because I believe it's important that everyone supports Canada in this particular moment.''

Keep ReadingShow less