By John Q. Hosedrinker 
Throughout his career, Donald Trump has always sought the approval of celebrities, a trait stemming from his desire to be liked by those he views as successful. However, as president, Trump has frequently clashed with numerous well-known figures, especially younger women, often leading to public disputes. This pattern extends beyond gender, as Trump has also feuded with male music stars over the use of their music and their political views. This conflict with celebrities may be due to the fact that these individuals break through the echo chamber of sycophants who surround him, providing him the only real contact with how he is seen in the real world.
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Megastars like Sabrina Carpenter loathe Trump, and that’s a problem because, in a nutshell, it truly gets under his skin.
Donald Trump, a man who built his fame on being famous, has always craved the approval of celebrities. Remember the cameos? The desire to be seen with the “cool kids”? It’s a fundamental part of his persona. Now, in the political arena, this desire to be liked clashes head-on with the reality that many of today’s most popular stars, particularly young women, are openly critical of him. Sabrina Carpenter’s recent condemnation of an ICE video using her music is just the latest example. Trump thrives on popularity, and the fact that a rising star like Carpenter, and countless others, disapprove – well, it’s something that evidently matters to him.
Trump’s insecurity is legendary. He loves to be around beautiful, successful people, and he thrives on their acceptance. Taylor Swift’s rejection, especially her endorsement of a Democrat, clearly stung. Publicly stating, “I HATE TAYLOR SWIFT” and even implying her attractiveness diminished after their falling out speaks volumes about how much this perceived disapproval affected him. This is not just about policy or political alignment; it’s personal. He clearly wants their validation.
The irony is thick. He has supporters, of course. People like Kid Rock and Jon Voight, and others, stand by him. But these allies don’t seem to satisfy his need for cultural relevance, for the sheen of coolness. It’s the mainstream acceptance, the kind of adoration that comes with being a cultural icon, that he truly desires. And that’s where the likes of Sabrina Carpenter come in.
It’s not just about the celebrities themselves, it’s about what they represent: the culture. Trump and his supporters want to control the narrative, to dictate what is considered “cool” and “acceptable.” But that’s a losing battle. The fact that the cultural zeitgeist largely excludes him, that the cool kids are, in many cases, actively opposed to him, is a deep wound. The use of pop songs in ICE videos, as an example, shows the administration’s willingness to use art, even if the artist dislikes Trump.
He is, in some ways, a creature of the media, feeding on attention, both positive and negative. But the disapproval of major stars – the people who define trends and influence the masses – hits him harder than the criticism of political opponents. It’s a constant reminder that he doesn’t have the clout, the cultural currency, that he so desperately craves.
He wants to be seen as a winner, to be adored, and to be considered “cool.” The fact that a generation of young, influential artists actively reject that image and condemn his actions, it cuts deep. Trump may enjoy the anger and outrage he provokes, but the sting of being disliked by the people at the top of the cultural ladder – the people who set the trends – that’s a different kind of pain.
The comments say that the reason for this is because Trump is a “loser” in the eyes of the cool kids. He has a lot of supporters, but a lot of enemies, and this is why those celebrities feel like they should be against him. Trump’s insecurity, and his craving for approval, make the disapproval of the mainstream a potent weapon. It’s a battle he’s losing, and one can infer that it’s a defeat he feels acutely. This is what truly kills him.