John Oliver Declares ‘Hamilton’ a Mistake After Watching Conservative Politicians Rap

John Oliver watched not one, but two conservative politicians rap during his main segment on “Last Week Tonight” on Sunday, and it brought him to one clear conclusion: “‘Hamilton’ was a mistake.”The first set of rhymes came from Anthony Constantino, the CEO of a sticker company, who President Trump endorsed in the House race for District 21 in upstate New York. Constantino grabbed major media attention when he put a giant “Vote for Trump” sign on his factory. “Constantino is running in a deep red district, but his race now seems up for grabs. And when you learn more about him, you can start to see why,” Oliver said. “For starters, he is a pro-Trump rapper, apparently, which is exactly as bad as you would expect.” To prove it, the HBO host then played a clip of a 2025 video from Constantino, in which he dropped a diss track about Zohran Mamdani. Among the lyrics was a line that went: “We know the terrorists’ dream is destroy New York. I want to make the whole world enjoy New York.” “‘Hamilton’ was a mistake,” Oliver immediately declared. “And yes, you heard right. He did just rhyme New York with New York there, which is frustrating given there were so many other options open to him, like fork, stork, or turning the camera off, packing up his recording equipment, and never rapping again.” Later in the segment, Oliver noted that Ohio gubernatorial candidate Vivek Ramaswamy also considers himself a rapper, and even freestyled during a radio interview last year. After watching that particular clip, Oliver made another assessment. “I can’t believe I’m about to say this, but Anthony Constantino is a better rapper,” he said.