Vanilla Ice Is In, Bret Michaels Is Out: Trump’s Battle for Celebrity Validation


A year and a half ago, Donald J. Trump seemed to have reached his cultural apex.

Post-election, professional athletes were doing “the Trump dance.” Elite podcasters were playing nice. He rang the bell at the New York Stock Exchange while standing beside a picture of his face on the cover of Time magazine’s Person of the Year issue. Carrie Underwood performed at his inauguration. The Capitol Rotunda that day was a bowl of mogul soup.

“Everybody wants to be my friend,” Mr. Trump marveled at his first news conference as president-elect.

Seventeen months after he made that observation, Mr. Trump’s pop culture capital appears to be on the wane. And while many athletes and some stars (Snoop Dogg and Nicki Minaj among them) have been happy to associate with him in his second term, lots of others won’t let their brands near his. It’s been a problem for a president who can’t help but politicize and put his name on just about everything he touches.

A trio of frustrated social media posts he made on Friday and Saturday showed how little power he has to force cultural figures to fall in line. Celebrities are harder to control than politicians. You can’t primary them.

The first post had to do with the Kennedy Center. He’s finally given up on it. The second post was about all the musicians who bailed on the state fair his administration planned for the country’s 250th anniversary. The third post blended the first two.

“We should have a giant MAKE AMERICA GREAT AGAIN RALLY, for 250, instead of having overpriced singers, who nobody wants to hear, whose music is boring, and yet who do nothing but complain,” he wrote. “Cancel it, just like I canceled my involvement with the failing and unsafe to be in Kennedy Center.”

Taken together, the three posts were a reminder that, more than a decade into his political project, the onetime reality television star turned president remains fixated and often tortured by celebrity.

All these dynamics were on display in the state fair fiasco. The Trump administration had booked a bunch of artists to perform in a series of concerts in Washington later this summer through a committee it set up called “Freedom 250.” None of the artists were exactly in the prime of their careers, but once it dawned on them that going ahead with this gig would associate them with Mr. Trump, they bolted, one by one.

“The artists were never told about any political involvement with the event,” Young MC wrote in a social media post dropping out. Poison frontman Bret Michaels, country singer Martina McBride and a founding member of Milli Vanilli all dropped too.

Pretty soon it seemed Vanilla Ice was the only one left.

He said in an interview with The New York Times this week it was a shame everyone couldn’t stop, collaborate and listen.

“I am so excited about this,” said the rapper, whose real name is Robert Van Winkle. “I figured everybody would be, and then a couple weeks go by, and then I see all these people dropping out, and I’m like, Why, why, why! Why would you drop out? This is a once in a lifetime thing.”

He lamented the whipsaw state of politics in 2026. “It’s like everybody’s got a fishing pole with a carrot, and you’re the rabbit, and they’re pulling it right, and pulling it left,” he said. “This country is not what it was in the 90s, man.”

He added, “I don’t vote, OK?”

It was Donald Trump Jr. who had personally asked him to perform in the concert series, when they were together at U.F.C. match attended by the president earlier this year, Mr. Van Winkle explained.

One senior administration official who requested anonymity to discuss these highly sensitive matters acknowledged that the rollout of the concert series was an unmitigated disaster but that Vanilla Ice’s professionalism was very much noted and appreciated by the White House.

When Mr. Trump finally posted about all of this, he let loose on the “third rate” artists who fled him. “I only want to be surrounded by Happy People, Smart People, Successful People,” he wrote. But he often seems to miss the days when he was surrounded by Famous People. On Tuesday he posted an old picture of himself and Whitney Houston without explanation.

After the artists pulled out on him, Mr. Trump announced he would perform instead. He billed himself as the “Number One Attraction” on earth, “the man who gets much larger audiences than Elvis in his prime.”

Some on the right were all shook up.

“I’m actually pretty pissed at how badly they’ve bungled America 250,” Matt Walsh, a prominent pundit at the Daily Wire, wrote in a viral social media post. “First they tried to invite Milli Vanilli and a bunch of other absurdly washed up geriatric on-hit wonders. Then when that didn’t work they decided to convert the event into a Trump rally where Trump will talk about himself for 90 minutes.”

What does it mean that even a herd of “one-hit wonders” wouldn’t dare associate with the president of the United States’ party for the nation’s 250th birthday? This question has inspired debate on the right about “whether or not there is mainstream acceptance for explicit MAGA politics,” as Jonathan Keeperman put it in an interview. He is the founder and editor of Passage Press, an independent publisher influential among conservative intellectuals and Trump administration fellow travelers. (He is known as “Lomez” on X).

“Can you assert support for Trump and MAGA within legacy cultural spaces without facing reputational costs?” Mr. Keeperman wondered. “The costs are less severe than before, but there are still costs. Clearly there are social pressures militating against an embrace of Trump specifically.”

Which brings us to the Donald J. Trump and John F. Kennedy Center for the Performing Arts.

After he took it over, Mr. Trump used the center like a playhouse in the purest sense. It was a place for him to perform acts of celebrity. He used it to stage a flashy night out complete with paparazzi for the opening of “Les Misérables.” He handpicked the Kennedy Center honorees and hosted the ceremony himself, which allowed him to hang around with celebrities including Gloria Gaynor and the members of KISS. The red carpet premiere of the Melania movie was there. “We need some glamour,” Mr. Trump told reporters that night. The only big celebrity who showed up was Ms. Minaj.

A painful paradox: The more he associated himself with the center, the less likely that anyone famous would show up there. Artists canceled. Ticket sales spiraled down. Slapping his own name on the building hastened its demise. After a judge ruled last week that his name had to come off, Mr. Trump posted 581 wounded words letting go.

“Unless I am free to do what I do better than anyone else, bring this Institution back, physically, financially, and artistically, I have no interest in continuing what could only be a hopeless journey into ‘NEVER NEVER LAND,’” he wrote.

The celebrity equation has been a complicated one for Mr. Trump. He won over tens of millions of people, enough to get him elected president twice, and he didn’t need the help of Bruce Springsteen, Taylor Swift or Beyoncé to do it. That was, for his supporters, part of the joy of their movement. They felt that together they were bigger than all the Hollywood bigshots who tried to stop them.

And yet, as this recent spate of posts reminds us, Mr. Trump still craves the company of celebrities. He sometimes talks about a theory he holds that many more famous people in Beverly Hills voted for him than will admit it.

Mr. Trump, who turns 80 this month, has pursued fame his entire adult life. His dreams came true: He is the most famous person in the world. But much of what he did to achieve that mantle has meant that other famous people don’t want to associate with him.

As Voltaire said, “What a heavy burden is a name that has become too famous.”



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