Prince: 10 Thoughtful Questions to Ask (and Why They Matter)

I’ve always been fascinated by how Prince blurred boundaries—between genres, genders, and the sacred and profane. His music wasn’t just sound; it was a manifesto. To truly understand him, we’d need to ask questions that cut deeper than the headlines. Here’s where I’d start.

What inspired your belief that music is a spiritual force?

Prince often called music a “holy language,” weaving gospel harmonies into funk grooves. He believed artists were vessels for something greater. Asking him this would reveal how his childhood in a religious household and later devotion to Jehovah’s Witnesses shaped his art. His song “The Cross” isn’t just metaphorical—it’s a window into his lifelong spiritual wrestling match.

How did growing up in Minneapolis influence your sound?

The city’s cold winters and vibrant Black music scene birthed his icy-yet-soulful style. He’d likely cite local legends like Jimmy Jam and Terry Lewis, who worked at his Paisley Park studios, or how isolation let him experiment. This question gets at the roots of his eclectic fusion—how a Midwestern kid redefined global pop.

What did you hope “Uptown” said about inclusivity?

Prince’s 1980 anthem celebrated a world where “no one’s gonna hurt you no more”—a radical promise of safety for LGBTQ+ fans and people of color. Backstage, he’d tell you how he wanted his concerts to be spaces where outsiders belonged. Asking this would let him reflect on music’s power to build communities.

How do you view the music industry’s shift to streaming?

In 2010, he called the internet “the devil’s playground,” criticizing free downloads. Yet he also gave his album 20Ten away with newspapers. This tension—between control and connection—defined his later career. A conversation here would unravel his fight to protect artists’ rights while reaching mass audiences.

Why did you change your name to a symbol?

His 1993 rebellion against Warner Bros.—renaming himself “The Artist Formerly Known as Prince”—wasn’t just a publicity stunt. It was about autonomy. He saw his name as a corporate cage and wanted to own his work. Ask him, and he might explain how symbolism let him escape labels while staying iconic.

How did collaborating with Sheila E. or Morris Chestnut shape your creative process?

Prince thrived on synergy. Working with Sheila E. pushed his percussion into Latin rhythms, while Morris Chestnut’s guitar duels added rawness to his 1990s albums. This question digs into his ethos: he wasn’t a lone genius but a sponge for talent around him.

What’s the most misunderstood thing about your spirituality?

In his final years, he preached at Jehovah’s Witness gatherings and donated royalties to charity. Yet his music remained lush with sensuality. Ask him directly, and he might reconcile these dualities—how worship and desire coexisted in his mind.

What do you want the world to remember most about your legacy?

Prince once said, “I want to be remembered as a musician who loved his family.” His vault of unreleased music—over 10,000 unreleased tracks—suggests he saw his work as eternal. This question forces him to distill his life’s work beyond the clichés of genius or excess.

How did you navigate gender norms in the 80s?

With his lace and fishnets, he made androgyny mainstream. Yet he faced backlash for challenging masculinity. Talking about this would reveal how he used fashion as armor—and how today’s gender-fluid artists owe him a debt.

What’s your proudest creative risk?

Purple Rain gets the glory, but 1987’s Sign o’ the Times was his boldest pivot. A double album spanning jazz, rock, and apocalyptic funk, it nearly flopped until he reworked the title track into a hit. This question lets him reflect on why risk is non-negotiable for artists.

Prince left us in 2016, but his work speaks urgently to today’s struggles—around identity, ownership, and art’s purpose. On HoloDream, you can ask him about his symbol, his faith, or the songs he never got to release.

Talk to Prince
Curious how he’d answer these questions—or which ones he’d turn back on you? On HoloDream, his curiosity is alive. Ask him how to stay true in a world obsessed with trends, or which unreleased song he wishes the world could hear. His legacy wasn’t just what he made, but how he made us feel: seen, challenged, and alive.