Overview of #2504 - Skylar Grey
Joe Rogan talks with singer-songwriter Skylar Grey about the role of emotion in music, the rise of AI-generated songs, her unusual path from a musical childhood in Wisconsin to major success in pop/hip-hop, and the creative pressure that came after writing “Love the Way You Lie”. The conversation also covers her life in Napa, her vineyard and wine projects, hunting and wildlife on her property, and her current album Wasted Potential—a personal record about growing up, identity, and reclaiming her story.
Main Topics Discussed
Music, AI, and “real” emotion
- Rogan and Grey open by talking about how music can carry deep emotional weight, using her song “Coming Home” as an example.
- They discuss AI-generated music and why, even if it sounds good, it still lacks the human connection listeners feel when they know a real person wrote and performed it.
- Both argue that technology can be a useful tool, but human imperfection, spirit, and lived experience are what make music feel meaningful.
Grey’s musical upbringing
- Grey was essentially raised in a musical family:
- mother played in folk bands and Celtic harp
- father sang in a barbershop quartet
- great-grandmother was an opera singer
- She was singing harmony as a toddler and performed her first show at age six with her mom.
- She toured the Midwest as a child, playing unusual venues like:
- libraries
- elementary schools
- women’s health conventions
- Boy Scouts events
- At 12, she bought her first grand piano with money she saved from performing and started writing pop songs on her own.
School, criticism, and early independence
- Grey says she hated school because it felt like time taken away from music.
- A teacher telling her “music isn’t a career” lit a fire under her, and she eventually dropped out at 16.
- Rogan uses that story to critique the education system and the way adults often discourage creative kids.
- They also connect this to ADHD-like traits and the idea that many creative people struggle in conventional school settings.
Early career failures and the LA grind
- Grey moved to Los Angeles at 17 and lived with the guitar player from Culture Club, Roy Hay, in Venice.
- Her first record deal under the name Holly Brook flopped, leaving her broke.
- She took survival jobs, including:
- working at Barnes & Noble
- teaching gymnastics
- editing porn
- She describes the porn-editing job as surreal and mentally corrosive, joking that she developed a “Tetris effect” of disturbing imagery.
- During that period, she was offered work as a keyboardist for Duncan Sheik, which helped her shift back toward music.
Breakthrough: moving to Oregon and writing hits
- Grey says she wrote in her journal that she wanted a cabin in the woods to make music in solitude.
- Shortly after, she found herself living in a small cabin in Oregon, hiking to it daily, with no internet and a separate bathroom.
- That isolation helped her reconnect with her creativity after depression and writer’s block.
- Her breakthrough came when she emailed beats from producer Alex da Kid and wrote the hook that became “Love the Way You Lie” in about 15 minutes.
- That song exploded globally, leading to high-profile opportunities, including work tied to Eminem and Diddy’s “Coming Home.”
Imposter syndrome and creative pressure
- Grey says the success of “Love the Way You Lie” made her feel intense pressure to repeat the hit.
- She struggled in collaborative songwriting sessions, often feeling shy and overwhelmed in rooms with strangers.
- She frequently left sessions feeling like she “sucked” or didn’t deserve her success.
- Rogan frames this as a common experience among genuinely creative people: big success often increases self-doubt rather than eliminating it.
- Grey says she eventually stopped taking many co-writing sessions because they drained her creatively.
Her creative process now
- Grey says she writes best when she is:
- alone
- away from Los Angeles
- not overthinking
- emotionally open
- She doesn’t force songs on a schedule; instead, ideas come while:
- showering
- cooking
- standing around waiting
- dealing with real life
- Rogan brings up The War of Art and the idea of “summoning the muse,” which fits Grey’s description of creativity as something that feels channeled rather than manufactured.
- She says she is currently in promotion mode and not writing much, but she wants to get back into a regular songwriting rhythm.
Napa life, wine, and ranching
- Grey moved from the isolation of Oregon into a more grounded rural life in Napa Valley.
- She and her partner own a property with a vineyard called Glass Rock.
- They sell grapes to winemakers who produce single-estate wines from their land.
- Their vineyard is:
- organically/biodynamically farmed
- dry-farmed
- managed with help from a French farmer
- Grey says she loves the peaceful ranch lifestyle because it balances the chaos of touring and industry life.
Wildlife, livestock, and predator problems
- A large portion of the conversation turns into animal and hunting stories.
- Grey describes repeated losses of chickens, sheep, and lambs to:
- coyotes
- bobcats
- foxes
- mountain lions
- One especially brutal story involves coyotes killing multiple chickens and a mountain lion killing lambs and a sheep on their property.
- Rogan and Grey discuss:
- livestock guardian dogs like Central Asian shepherds/Kangal-type dogs
- how predators behave
- how mountain lions communicate with a whistle-like sound
- how wildlife management works when predators become a serious threat
Hunting and wild game
- Rogan and Grey talk extensively about hunting and eating wild game:
- elk
- bear
- axis deer
- mountain lion
- She says she helps process deer and grew up around hunting.
- Rogan praises wild game as healthier, more ethical, and more connected to nature than store-bought meat.
- They discuss axis deer in Hawaii, especially on Lanai, where the population is enormous and hunting is almost guaranteed if you go with a rifle.
- Rogan also explains how some restaurant “elk” is likely farmed or sourced from New Zealand rather than truly wild American elk.
Key Takeaways
- Human-made art still matters: Both guests believe AI may mimic style, but it can’t replace the emotional connection of a real person’s lived experience.
- Success can create pressure: Grey’s biggest hit became both a launching pad and a source of insecurity.
- Solitude fuels creativity: Grey says she does her best work when she’s away from industry noise and surrounding expectations.
- Nature is grounding: Her life in Napa, with animals and land, is a major contrast to the stress of Los Angeles and touring.
- Her new album is personal: Wasted Potential is framed as a confessional, coming-of-age project that revisits her Wisconsin upbringing, sexuality, and career regrets.
Album Mentioned
Wasted Potential
- Grey says the album is about:
- growing up in small-town Wisconsin
- discovering her sexuality
- revisiting childhood and early ambition
- confronting regret and self-criticism
- She admits she has felt she “wasted” some of her early potential by not pushing harder during key moments in her career.
- At the same time, she says she now wants to be more playful, less perfectionistic, and more consistent with releasing music.
Notable Themes
- Creativity vs. industry expectations
- The value of imperfection in art
- The tension between ambition and self-doubt
- Living close to nature as a counterweight to fame
- The emotional authenticity of songwriting