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

Inside ‘Off Campus,’ the Latest Hockey-Romance TV Hit

Ella Bright and Belmont Cameli in ‘Off Campus.’

Liane Hentscher/Prime

Inside ‘Off Campus,’ the Latest Hockey-Romance TV Hit

In hockey, the best advice is to leave everything on the ice. But in the world of hockey romance, the focus is on what happens after the players’ skates — among other things — come off. It’s a winning formula that has just spawned another TV sensation.

Released May 13, Off Campus is Prime Video’s entry into the explosively popular genre. Based on the 2015 book The Deal, by romance author Elle Kennedy, the series follows a group of college hockey stars at the fictional Briar University and the women they fall in love with. Off Campus uses the messy lives of these athletes to explore romance tropes like fake-dating plots, enemies-to-lovers twists, secret relationships, and more. The series also taps into the current craze of new-adult stories — that is, focused on characters in that stage of life between teen and full-fledged adulthood — many specifically set in the pressure-cooker environment that college and university settings naturally supply to make romance spark. And following the success of the steamy HBO Max hit Heated Rivalry, Off Campus is a high-budget argument from Prime Video and creator Louisa Levy that hockey romance isn’t a phase — it’s a genre with plenty to say.

Keep ReadingShow less
Jimmy Kimmel Criticizes Trump for Being ‘Too Busy for His Son’s Wedding’

Jimmy Kimmel on 'Jimmy Kimmel Live'

YouTube/Jimmy Kimmel Live

Jimmy Kimmel Criticizes Trump for Being ‘Too Busy for His Son’s Wedding’

Jimmy Kimmel took aim at Donald Trump‘s decision to skip out on Donald Trump Jr.‘s wedding because of “circumstances pertaining to government.”

On the latest episode of Jimmy Kimmel Live, the late-night host explained that Don Jr. held his nuptials with Bettina Anderson on a private island in the Bahamas last weekend. “It was a small ceremony with about 40 guests, none of whom were his father,” Kimmel said. “Daddy Donald sent his RSVP via Truth Social.”

Keep ReadingShow less
Bad Bunny Will Bring a Slice to Life in ‘Toy Story 5’

Bad Bunny performs in concert during his “DeBI TiRAR MaS FOToS” Tour at Estadi Olimpic Lluis Companys on May 22, 2026 in Barcelona, Spain.

Xavi Torrent/Getty Images

Bad Bunny Will Bring a Slice to Life in ‘Toy Story 5’

Bad Bunny will take his colorful personality to the world of animation, with the Puerto Rican star announced as part of the cast of the upcoming Toy Story 5 film.

On Tuesday (May 26), Disney confirmed that the Grammy Award-winning artist will make a cameo appearance in the fifth installment of the popular film franchise as Pizza with Sunglasses. Described as “effortlessly cool and mysterious,” Pizza with Sunglasses is part of a small, but strong group of forgotten toys living in an abandoned shed.

Keep ReadingShow less
‘The Simpsons’ Writer Who Accidentally Predicted Trump’s Presidency Launches His Own 2028 Bid

Dan Greaney, who penned 'Bart to the Future,' announced his bid for the White House.

THE SIMPSONS © 2025 by 20th Television; Instagram

‘The Simpsons’ Writer Who Accidentally Predicted Trump’s Presidency Launches His Own 2028 Bid

Dan Greaney, The Simpsons writer who accidentally prophesied Trump would become president of the United States, is now making his own 2028 bid for the White House.

Greaney announced his run in an Instagram video Tuesday, dressed in a massive grey wig and blue robe — a nod to his nickname as “The Prophet.” Self-described as “a progressive Republican” in his bio, the writer-producer made his case for the presidency.

Keep ReadingShow less
Paul McCartney and Paul Mescal Talk ‘Boys of Dungeon Lane’ in Short Film

Paul McCartney and Paul Mescal

Amazon

Paul McCartney and Paul Mescal Talk ‘Boys of Dungeon Lane’ in Short Film

Paul McCartney sat down with Paul Mescal, the actor who portrays him in the upcoming films about the Beatles, to discuss his new album.

The two Pauls sat down “In Conversation” for an exclusive short film posted by Amazon. In the 10-minute chat in the same restaurant the album trailer was filmed, the rocker and the actor talked about the nostalgic The Boys of Dungeon Lane.

Keep ReadingShow less