Today, Right-wing commentator Matt Walsh tore into the organisers of Donald Trump’s “Freedom 250” concerts after the rock star Bret Michaels became the fifth of nine announced acts to walk away. According to Variety, Michaels said the show had “evolved into something much more divisive” than the patriotic celebration he agreed to, and cited unspecified threats against his band. Morris Day, Young MC, the Commodores, Milli Vanilli, and the country singer Martina McBride — an assortment whose biggest hits land somewhere between 1977 and the turn of the millennium — had already bailed. That leaves Vanilla Ice, of “Ice Ice Baby” fame, to headline the nation’s 250th birthday on the National Mall, the centrepiece of a season of events Trump built to put himself and his brand at the heart of America’s semiquincentennial.

Walsh’s complaint — that the organisers booked “washed up has-beens” only to watch the has-beens flee — points to something more significant than one lame gig running low on big names. The American Right won the White House two years ago and claims tens of millions of voters, yet it cannot put a single current A-list entertainer on a stage. The cause, to be sure, is structural and class-based. Entertainment is gatekept by exactly the sort of urban, degree-holding professionals who loathe Trump, and any star who might break ranks knows it.

The issue is that MAGA is happy to take whoever answers the phone. Trump’s 2025 inauguration leaned on the 82-year-old Lee Greenwood, who has now sung “God Bless the USA” at both of his inaugurations, alongside the Village People and Kid Rock. Trump’s 2017 swearing-in struggled to attract headliners as well, falling back on country acts and legacy rockers after a parade of bigger names said no. In February, Turning Point USA staged a counter-Super Bowl around a Kid Rock set so out of time that viewers accused him of lip-syncing through “Bawitdaba”. That broadcast drew roughly 21 million YouTube views against the 128 million who watched Bad Bunny’s official halftime show. Even Trump tuned in to Bad Bunny at his own watch party, though he apparently detested it.

Any rare popular name the Right gets to claim, a Shane Gillis or an Oliver Anthony, tends to edge away the moment the embrace turns into a branding exercise. Country is the one mainstream genre that still mints Right-leaning stars, yet its biggest sellers keep their distance from campaign branding. It’s no wonder, then, that Freedom 250 could not land them. It even lost Martina McBride, whose biggest hits are 30 years old.

The Right was not always this culturally impoverished. Ronald Reagan was a working actor before he reached the White House. Frank Sinatra sang for him, Bob Hope entertained Republican audiences for decades, John Wayne dominated the box office, and Charlton Heston led the National Rifle Association after his Hollywood heyday. Now they’re reaching for Vanilla Ice.

For now, with Hulk Hogan dead and the bench of willing athletes and entertainers thinning, the American Right’s cultural arsenal is ageing alongside its increasingly unpopular 79-year-old leader. The 2026 line-up looks weaker than 2024’s, which was hardly a parade of celebrity heavyweights. Electoral victory does not require the endorsement of progressive Hollywood stars — MAGA has demonstrated as much twice over. But a movement that cannot elevate one convincing younger performer is showing unmistakable signs of cultural decline.

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Oliver Bateman is a historian and journalist based in Pittsburgh. He blogs, vlogs, and podcasts at his Substack, Oliver Bateman Does the Work

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