With the thinly veiled insecurity of someone who has become famous for being famous, Trump has always wanted other famous people to like him
Long before he was a politician, Donald Trump was a celebrity – and with the thinly veiled insecurity of someone who’s become famous for being famous, rather than acting, singing or a similarly conventional route, he’s always wanted famous people to like him.
Famously, it was easy to get permission to film a movie or TV show at one of Trump’s properties if you’d comply with one catch – a cameo for Trump himself. These were usually cut before the final edit, but Trump made it in here and there, most famously in Home Alone 2. Celebrities are rich, good-looking and successful – Trump’s three favourite things. He finds it irresistible.
The problem for Trump in his latest incarnation, as the endlessly divisive Maga President, then, is that he seems to be in almost constant conflict with some of America’s best-loved celebrities – especially when they happen to be younger women.
This week, Sabrina Carpenter became the latest star to clash with Trump’s administration, after an official Immigration and Customs Enforcement (ICE) account on X posted a video showing ICE agents rounding up alleged “illegal immigrants” for deportation, set to her song Juno. She condemned the video as “evil and disgusting”, adding “do not ever involve me or my music to benefit your inhumane agenda”.
Carpenter and her team must surely be braced for backlash, as it’s happened many times before. Taylor Swift should, in theory, be a Maga icon – she’s a conventionally attractive white woman, with country music roots, who has turned herself into a billionaire through her talent and business acumen. More than that, she’s engaged to one of the most famous American footballers in the country.
You simply do not get more appealing to middle America than that – but the usually apolitical Swift endorsed Democrat Kamala Harris in 2024, and spoke out against Trump’s crackdown on abortion rights. That was enough to have Trump posting that “I HATE TAYLOR SWIFT” on more than one occasion, even claiming that after he said that, she became less attractive.
In May 2025, four months into his second term as US President, the most powerful man in the free world, he posted: “Has anyone noticed that, since I said ‘I HATE TAYLOR SWIFT,’ she’s no longer ‘HOT?’”
Beyoncé has been in line for even harsher criticism, for almost a decade, after appearing at a Clinton rally. This has recently escalated into calls for Beyoncé to be prosecuted alongside Trump’s other enemies, in this case over an exaggerated conspiracy theory that she only endorsed Harris in exchange for a payout of millions (though the campaign did cover costs for her appearance).
Trump has similarly castigated singer Rihanna, after she refused permission for his music to be used at rallies, called Madonna “disgusting” and “disgraceful to our country” for criticising him, and has even attacked the actress Meryl Streep and talk show host Oprah Winfrey – usually so beloved as to be beyond criticism – for not being on his side.
It is tempting to see a pattern here, especially from a president like Trump, who has been adjudicated by a civil court to have sexually assaulted at least one woman, and who has been accused of sexually harassing many more. Trump’s twisted attitudes towards women surely fuel some of his anger – as evidenced by his notorious “bleeding from her…” comments about Megyn Kelly, then of Fox News, after she asked him challenging questions at a TV debate.
But there is something more going on – Trump has managed to fight with numerous male music stars, too, including several he clearly regarded as his heroes, or hoped might be his buddies.
Trump’s ongoing feud with Bruce Springsteen over the use of Born in the USA – surely second only to The Police’s I’ll Be Watching You as the world’s most misunderstood track – is perhaps his most notable, leading Springsteen to break with much of his fanbase and openly oppose Trump.
But he has managed to be in dispute with Aerosmith, REM, Neil Young, Creedence Clearwater Revival and even Kenny Loggins over use of music. Trump is at war with the authors of half of America’s classic rock playlist.
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The reality of Trump’s life is that he is surrounded by sycophants, who only tell him how brilliant he is, how great his ideas are and how universally beloved he is by anyone who matters. He has set things up so they work that way, and made sure nothing else gets in.
Celebrities, bizarrely, are the one set of people who break that bubble – people he’s aware of, and is sure must think he’s as great as everyone else does, only for them to let him down again, and again and again.
Trump’s allies pass this off as an out-of-touch liberal Hollywood elite, and their base will surely lap that up. The reality, though, is even stranger. The public disdain of America’s A-listers is Trump’s only contact with how he’s seen in the real world. No wonder he hates it so.
