#2504 - Skylar Grey

Episode of The Joe Rogan Experience · May 22, 2026 · 2 h 5 min

Joe Rogan talks with singer-songwriter Skylar Grey about AI music, her childhood performing career, writing "Love the Way You Lie," ranch life, mountain lions, and creativity.

Summary

Singer-songwriter Skylar Grey joined Joe Rogan to promote her album "Wasted Potential." They opened by discussing AI-generated music; Grey said she viewed AI as another creative tool like Auto-Tune but doubted it could yet write with real emotion, while Rogan argued people would value human-made art more. Grey recounted growing up in a musical family in Mazomanie, Wisconsin, touring the Midwest with her mother from age six, going solo around 12, and dropping out of school at 16 after an algebra teacher told her music was not a career. Rogan related his own discouraging art teacher and argued teachers should be paid far more.

Grey described moving to Los Angeles at 17, a failed Warner Bros. deal under the name Holly Brook, working briefly editing pornography, touring as Duncan Sheik's keyboardist, and retreating to a cabin on the southern Oregon coast. From there she wrote the hook for "Love the Way You Lie" with producer Alex da Kid, which became a number-one hit and led to work with Eminem and Diddy, along with imposter syndrome and pressure in co-writing sessions.

Much of the conversation covered rural life: Grey's biodynamic, dry-farmed Napa vineyard, losing livestock to coyotes and two mountain lions, and hunting. Rogan discussed Sundarbans tigers, axis deer hunting on Lanai, Maui Nui venison, and the ban on selling wild game. They closed on creative process, including Steven Pressfield's "The War of Art," nature's effect on the mind, and Grey's goal of releasing an album every year after turning 40.

Chapters

1:05
AI and real music
Rogan and Grey discuss AI-generated songs and whether technology can replace human emotion in art.
6:43
Musical childhood in Wisconsin
Grey describes performing with her mother from age six, going solo, and dropping out after a teacher dismissed music as a career.
13:37
Teachers and education
Rogan shares his own discouraging art teacher and argues for higher teacher pay, with pay figures looked up live.
20:55
Moving to LA and Detroit's decline
Grey recalls arriving in LA at 17, prompting Rogan to discuss LA's decline and Detroit's collapse in Roger & Me.
34:36
Napa ranch and vineyard
Grey describes losing chickens to coyotes, her biodynamic dry-farmed vineyard, and meeting her partner Elliot.
49:02
Early career struggles and Oregon cabin
Grey recounts her flopped first album, odd jobs including editing porn, touring with Duncan Sheik, and moving to a remote cabin.
57:52
Tigers and mountain lions
Rogan discusses Sundarbans tiger attacks and Grey recounts two mountain lions killing 17 sheep on her property.
1:15:52
Wild game and hunting
Rogan describes eating game meat, axis deer hunting on Lanai, and why wild game can't be sold in the US.
1:26:05
Love the Way You Lie and imposter syndrome
Grey explains how she wrote the hit hook from the cabin and struggled with pressure afterward.
1:35:42
Creative process
They compare songwriting and comedy writing methods, The War of Art, and the benefits of nature.
1:49:22
Goals and Wasted Potential
Grey discusses turning 40, releasing music more often, and the coming-of-age themes of her new album.

Key points

What was said, by whom, with the exact words. Timestamps jump to the moment.

Skylar Grey
Grey argues AI is simply another tool for creatives, comparable to Auto-Tune and computers when they were introduced.
“To me, I see them as just tools that creatives can use to get their vision across”
Listen from 2:56 · Artificial intelligence in music
Joe Rogan
Rogan argues AI will make people more appreciative of real physical things, human connection, and real art.
“I think it makes you really appreciate actual things like real physical things”
Listen from 5:24 · Artificial intelligence in music
Skylar Grey
Grey predicts AI will lead people to value human-made art, nuance, and imperfection more.
“it'll make us value real human made art more and value like nuance and mistakes and things not being perfect”
Listen from 6:00 · Artificial intelligence in music
Skylar Grey
Grey recounts that an algebra teacher telling her music was not a career motivated her to drop out and pursue music.
“She told me music isn't a career. And I was like, I'll show you, bitch”
Listen from 11:56
Joe Rogan
Rogan argues that if society valued the future, it would pay teachers very well to attract the best ones.
“if we really cared about the future of Earth, we would spend a ton of money making sure that these teachers are really well educated”
Listen from 14:21 · Teacher pay in the United States
Joe Rogan
Rogan says he regards ADHD-like traits as a superpower rather than a negative.
“I think it's a fucking superpower”
Listen from 16:41 · Attention deficit hyperactivity disorder
Skylar Grey
Grey says many music industry 'experts' are failed, bitter artists telling others how to proceed.
“a lot of the experts in the game are just people who were artists and didn't make it, and now they're bitter”
Listen from 20:23
Skylar Grey
Grey explains that dry farming makes vines struggle so roots reach deeper, producing more concentrated flavor.
“it makes the vines struggle in a good way. So it makes them reach deeper, like the roots reach deeper into the ground”
Listen from 41:47 · Biodynamic viticulture in Napa Valley
Skylar Grey
Grey recounts that the hook she sent Alex da Kid from an Oregon cafe became a number-one song a month later.
“the first one I did was called Love the Way You Lie. And a month after I sent Alex that hook, it was a number one song”
Listen from 1:27:05 · Love the Way You Lie
Skylar Grey
Grey says the hit gave her imposter syndrome because the hook took only 15 minutes to write.
“I definitely had a little imposter syndrome when I wrote that song, because I was just like, that was too easy”
Listen from 1:30:02 · Impostor syndrome
Joe Rogan
Rogan argues imposter syndrome is common among genuinely creative people and is a good sign.
“Everybody that I've ever met who's really good has imposter syndrome”
Listen from 1:33:15 · Impostor syndrome
Skylar Grey
Grey says her songs that come with less effort tend to be better than ones she overthinks.
“The songs that take less effort tend to be the better songs. And the songs that I slave over to try to get them perfect and overthink, they end up doing nothing”
Listen from 1:36:32 · Songwriting creative process
Joe Rogan
Rogan describes his comedy writing as free writing on a subject, then extracting and expanding ideas, calling it a numbers game.
“It's just a numbers and time game. The amount of numbers, the amount of time that you spend writing”
Listen from 1:41:19 · Songwriting creative process
Joe Rogan
Rogan argues that time in wilderness is like a vitamin people need.
“I think everybody who goes to the woods realizes they need it. I think it's a vitamin”
Listen from 1:47:02
Skylar Grey
Grey states her goal is to release an album every year rather than every five years.
“my goal in regards to that is to put out an album every year instead of every five years”
Listen from 1:49:34 · Wasted Potential (Skylar Grey album)
Linked moment · 1:54:05Skip to 1:54:05 using a listen link in the info box.
Skylar Grey
Grey describes Wasted Potential as a coming-of-age album about her small-town Wisconsin upbringing and discovering her sexuality.
“it's an album where I'm telling the story of my like upbringing in small town, Wisconsin. Um, discovering my sexuality”
Listen from 1:54:05 · Wasted Potential (Skylar Grey album)
Skylar Grey
Grey blames her career failures on her own laziness and lack of effort when she was younger.
“All the failures that I've had, I realized were my fault for being, you know, lazy or not putting in the effort and the grind”
Listen from 1:56:16

People

In the conversation

Joe RoganAmerican comedian and host of The Joe Rogan Experience
Skylar GreyGrammy-nominated American singer, songwriter, and producer

Discussed

EminemRapper cited in an anecdote about the moment fame hits
Alex da KidBritish record producer who co-created "Love the Way You Lie" with Grey
Duncan SheikAmerican singer-songwriter for whom Grey played keyboards on tour
Roy HayCulture Club guitarist whose Venice couch Grey slept on at 17
Carlo MondaviWinemaker and grandson of Robert Mondavi, friend of Grey's partner
Steven PressfieldAmerican author of books on creativity including The Artist's Journey
Michael MooreDocumentary filmmaker who made Roger & Me
Steven RinellaHunter and host of MeatEater
John MellencampAmerican rock musician

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From the publisher

Skylar Grey is a Grammy Award-nominated singer, songwriter, and producer. Her new album, “Wasted Potential,” is available now.https://ffm.to/sg_wastedpotential.OPRwww.youtube.com/@SkylarGreywww.skylargreymusic.com Perplexity: Download the app or ask Perplexity anything at https://pplx.ai/rogan. Get 30% off + 2 free gifts at https://ARMRA.com/rogan Learn more about your ad choices. Visit podcastchoices.com/adchoices

Summary, chapters and key points were generated from the episode transcript on September 28, 2026. Quotes are checked word for word against the transcript.

Categories: Music Interviews·Wilderness