Chappell Roan Reflects on Meeting Idol Miley Cyrus and the Full-Circle Moment of Stardom

In a delightful revelation that has music fans buzzing, Chappell Roan, the charismatic “Midwest Princess” currently soaring through the pop landscape, recently shared an unforgettable encounter with global superstar Miley Cyrus. The “Casual” singer opened up about getting to spend a night hanging out with the “Wrecking Ball” pop icon, detailing the surreal experience during a candid interview on The Comment Section podcast hosted by Drew Afualo on Wednesday, July 17. This meeting marks a truly full-circle moment for Roan, whose burgeoning career continues to captivate audiences worldwide, drawing parallels and connections that resonate deeply with her own artistic journey and the dreams she harbored as a young fan.

Chappell Roan, whose real name is Kayleigh Rose Amstutz, has witnessed an astronomical rise to fame that she openly admits has been nothing short of extraordinary and largely unexpected. The 26-year-old artist, celebrated for her vibrant stage presence and anthemic pop tracks, expressed profound gratitude for the whirlwind of success she’s currently navigating. “All these things that are happening to me now are just kind of icing on the cake,” she told Afualo, reflecting on the luxurious perks that have come with her newfound celebrity. “I never thought I could fly first class. You know what I mean? I never thought I would get access to so much backstage.” This sentiment underscores a humility that fans find incredibly endearing, showcasing an artist genuinely surprised and thrilled by the trajectory of her career, embracing every moment as a dream realized far beyond her initial expectations. Her journey from aspiring musician to commanding massive festival stages and selling out tours across the globe is a testament to her unique vision and undeniable talent.

One of the most thrilling anecdotes from the podcast interview involved an unexpected invitation from none other than Miley Cyrus herself. Chappell recounted how Miley, 31, extended an invitation to a party, leading to an evening filled with conversation and a moment of shared history. During their interaction, Chappell couldn’t resist revealing a deeply personal connection she has had with Cyrus for years. “Miley invited me to a party, and I was like, ‘You don’t know that you were my first concert when the Jonas Brothers were opening for you,'” Chappell recalled, highlighting the surreal nature of meeting an idol who had played such a foundational role in her early appreciation for live music. This revelation undoubtedly created a special bond between the two artists, showcasing how the paths of influence and inspiration can intertwine in the vibrant tapestry of the music industry. For Chappell, who now stands as a prominent figure herself, this interaction with a childhood hero like Miley Cyrus serves as a powerful validation of her journey and the impact she is now having on others.

The conversation naturally steered towards the immense influence of Miley Cyrus’s iconic alter ego, Hannah Montana, a character whose concept of dual identities resonated profoundly with Chappell Roan. The “Hot to Go” singer delved into how the Disney Channel show and its central premise — a teenager living a secret life as a pop star — left a lasting impression on her artistic sensibilities. “I loved that Hannah had two different personalities because it’s my f—ing hair that gets me in trouble all the time. So, I wish I would’ve done her,” Chappell candidly admitted. This playful remark not only highlights Chappell’s signature wit but also touches upon deeper themes of identity, performance, and the persona artists cultivate. For Chappell Roan, her “Midwest Princess” persona is a carefully crafted yet authentic extension of herself, much like Hannah Montana was for Miley Stewart. The ability to switch between Kayleigh Rose Amstutz and Chappell Roan, embracing distinct facets of her being, mirrors the very essence of the Hannah Montana narrative, illustrating the power of theatricality and character in pop music.

Beyond the personal connection, Chappell expanded on the enduring legacy of Hannah Montana, a show that defined a generation and explored the complexities of balancing a normal life with superstardom. The concept of a hidden identity, where a regular person could transform into a dazzling pop icon simply by donning a wig, captivated millions, including a young Chappell Roan. This theme of transformation and the freedom it offers to explore different facets of one’s personality is clearly something Chappell embraces in her own artistry. Her vibrant, often campy, and unapologetically queer aesthetic as Chappell Roan is a deliberate choice, allowing her to express truths and emotions that might feel different under her given name. The “f—ing hair” comment, while lighthearted, signifies how outward appearances and chosen aesthetics become integral to the persona, a protective and empowering shield that allows for greater artistic expression and bolder performances, much like Hannah Montana’s blonde wig served as her portal to pop stardom.

Recalling her very first concert, the formative Miley Cyrus show where the Jonas Brothers opened, Chappell painted a vivid picture of childhood wonder and confusion. She described attending the concert with her classmates, witnessing an emotional phenomenon unfold around her that she, at the time, couldn’t fully grasp. “I saw my friends start crying, and then little girls around us started crying, and I was like, ‘I guess I’ve gotta cry.’ I was like, ‘This is so emotional,'” she admitted, humorously detailing her initial, somewhat performative, reaction to the overwhelming atmosphere. However, as an adult and now an artist herself, Chappell has gained a profound understanding of that moment. “I didn’t understand then why people were crying, but now I get it. I’m like, ‘Oh, because that was the coolest thing.’ It was so spiritual.” This realization speaks volumes about the transformative power of live music and the deep, often ineffable connection artists forge with their fans. It was not just a concert; it was an experience that transcended entertainment, touching something “spiritual” within the attendees, a feeling Chappell now aims to evoke in her own performances, understanding intimately the emotional weight and profound impact she can have on her audience.

The “Midwest Princess” has often spoken about creating spaces where people feel free to be themselves, echoing the liberating spirit she encountered at that very first concert. Her own shows are renowned for their celebratory atmosphere, where glitter, self-expression, and a sense of community thrive. This retrospective understanding of her first concert experience provides crucial insight into the kind of artist Chappell Roan has become—one who understands the immense emotional investment fans place in their idols and the profound impact a live performance can have. Her connection with Miley Cyrus, a pioneer in navigating celebrity from a young age and constantly reinventing her image, feels particularly poignant given Chappell’s own journey of self-discovery and artistic evolution. This meeting of two pop generations, one an established icon and the other a rapidly ascending star, highlights the timeless threads of inspiration, influence, and the sheer magic that continues to define the world of pop music, forever linking the dreams of a young fan to the reality of a celebrated artist.