Conservative political commentator Charlie Kirk caused no shortage of controversy throughout his lifetime for his criticism of celebrities. Kirk died after he was shot during a speech at Utah Valley University in September 2025. While Kirk was a frequent critic of Hollywood culture, he did ally with conservative celebrities such as Kansas City Chiefs' Harrison Butker and even defended Sydney Sweeney over her American Eagle controversy. (Sweeney and American Eagle were accused of using an ad about "great jeans" as a double entendre for the discredited theory of eugenics, a racially biased study that was notoriously adopted with the Nazi party and has been often associated with white supremacy.) Who Was Charlie Kirk? Meet the Late Turning Point USA Founder "We don't know how conservative [Sweeney] is, to be clear, but she doesn't have to default to being a lib[eral] just to survive as a celebrity," Kirk told podcast listeners. Charlie Kirk Justin Sullivan/Getty Images Keep scrolling for Kirk's criticism and rare praise for celebrities below: Sydney Sweeney Kirk addressed the scandal over Sweeney's American Eagle advertisement on his podcast in August 2025. He also mentioned that some of Sweeney's fans were confused and upset that she was reportedly a registered Republican in the state of Florida. "Sydney Sweeney is a right-winger and this has people very confused and surprised," he told listeners in August 2025. "If this has people surprised, you haven't been paying attention to how young people have been moving to the right." Sydney Sweeney in September 2025. Emma McIntyre/Getty Images Kirk suggested that there was a "very simple explanation" for both Sweeney's advertisement and her party affiliation. "Sydney Sweeney, she knows her audience," he insisted. "Her audience is a bunch of young, Gen Z males who have been moving dramatically to the right ... You have to imagine [this controversy] is only going to further radicalize her to the right. She's an All-American girl. She grew up near Spokane, right near the Idaho border. We don't know how conservative she is, to be clear, but she doesn't have to default to being a lib[eral] just to survive as a celebrity." Taylor Swift On an August 2025 podcast episode, Kirk reacted to Swift's engagement to Kelce by suggesting that one of the reasons she was "annoyingly liberal over the last couple of years" was because she was "not yet married and she doesn't have children," according to Media Matters. "I say this non-sarcastically," he added. "I say this as a husband and a father. Having children changes you. Getting married changes you, and I hope that America's biggest pop star marrying the pharmaceutical spokesperson ends up conservatizing them. Taylor Swift might deradicalize herself. She might come back down to reality." Kirk went one step further by suggesting that Swift could "become more conservative" once she got "married and [had] a ton of children." Charlie Kirk's Final Words Included Debate on Gun Violence "Engage in reality more and get outside of the abstract clouds. Reject feminism. Submit to your husband, Taylor. You're not in charge," he insisted. "And most importantly, I can't wait to go to a Taylor Kelce concert. I can't say it without laughing. You've got to change your name. If not, you don't really mean it." Many Swifites condemned Kirk for ordering Swift - who endorsed Kamala Harris for President in 2024 - to "submit" to Kelce, with one fan simply replying via Facebook: "F that asshat." "Like anyone listens to Charlie," another Swiftie responded. Russell Brand Kirk had former comedian-turned-right wing commentator Brand on his podcast in August 2025 to discuss the latter's conversion to evangelical Christianity. While discussing the way Brand's formerly wild lifestyle led him to seek answers from a higher power, Kirk wished his guest well on his spiritual journey. "You have millions of people praying for you," he told Brand. "The Christian journey is not necessarily easy, but you can rest [knowing] that Jesus is with you throughout every step of it. Your whole thing is freedom, where the spirit of the lord is, there is liberty." Following Kirk's death, Brand referred to Kirk as a "good, strange Christian man," adding: "Dear God please comfort his family." Miley Cyrus Kirk weighed in on Cyrus' iconic performance at the MTV Video Music Awards in August 2013 by accusing her of contributing to the moral "decline" of the U.S. with her skimpy wardrobe and raunchy stage banter. "Miley Cyrus embodies the decline of our moral fabric in this country. Absolutely disgusting," he wrote on Twitter (now X) at the time. Miley Cyrus performs during the 2013 MTV Video Music Awards. Jeff Kravitz/FilmMagic for MTV Cyrus never directly responded to Kirk, though her manager Larry Rudolph told Us Weekly exclusively at the time that the performance "could not have gone better." "The fans got it. The rest eventually will," he predicted. Cyrus later said in an MTV documentar