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Key Points Kenny Chesney discussed personal political opinions in a rare appearance on Bill Maher's show. Chesney shared a political anecdote involving his grandfather. He described how diverse friendships changed his music and sense of self. Kenny Chesney made rare political comments to Bill Maher during an appearance on the comedian’s late-night show. On the Friday, Nov. 7 episode of Real Time With Bill Maher, Chesney briefly touched on politics — a topic the “She Thinks My Tractor’s Sexy” singer typically steers clear from. 🎬 SIGN UP for Parade’s Daily newsletter to get the latest pop culture news & celebrity interviews delivered right to your inbox 🎬 “Tell your people that my people mean no disrespect by that ,” Maher joked to Chesney after mentioning that Real Time doesn’t have many country music stars as guests. “It’s a political show, and I know you’re not political.” To that, Chesney pointed out, “That doesn’t mean I don’t have my own opinions,” to which Maher reiterated, “OK, but we’re not going to press you on those unless you want.” That’s when the country legend shared a political anecdote, telling Maher, “When I was a child, my grandfather was a Democrat, and he worked for TVA in Oakridge, in East Tennessee. And I asked him, I said, ‘Are you a Democrat or a Republican?’ And he goes, ‘I’m a Democrat, but I’m saving up to be a Republican.'” Oops! We’re unable to load this content right now. View directly on Instagram Related: Tim McGraw Sends Bold Political Message That Firmly Divides Fans Additionally, Chesney spoke about how his music has changed after being exposed to people who did not grow up like he did in Luttrell, Tenn. “I learned when I started spending a lot of time in the Virgin Islands and I met a lot of people that grew up very differently, that had different religious beliefs, that had different political beliefs. And they just didn’t look or talk like me,” he explained. “But they became really great friends and all of a sudden, I had a circle of family down there that was very different. And I realized I could make music for them, too.” The “When the Sun Goes Down” singer continued, “Before that, I didn’t know that it was OK because I was just trying to fit a certain formula that was working. And when you’re young, you just want to get your songs on the radio. I didn’t know who I wanted to be. I wasn’t comfortable in my skin at all.” The country icon’s book, Heart Life Music, was released on Nov. 4.
