In 2006, when she was 20 years old and went by the name Holly Brook, Skylar Grey released her Warner Bros. debut, Like Blood Like Honey, a collection of Sarah McLachlan-style piano ballads. It tanked.

After the label dropped her, Grey left L.A. for Oakview, California, and found work in an unlikely field—editing porn—before eventually retreating further into the backwoods of southern Oregon. "I went through a few years where I felt like a failure," she says of her time in the wildnerness. "I was a naive girl from Wisconsin who didn't know anything about the music industry."

Out of XXX video and seclusion came one of the more stunning career transformations in recent memory. In 2010, Grey adopted her new name—a nod to the Pacific Northwest weather—and presented the deeply personal songs she'd written during her self-imposed exile to a VP at Universal Publishing, who introduced her to Wonderland Music producer Alex da Kid. The pair began trading e-mails and music and soon delivered a track that became the Eminem single "Love the Way You Lie," with Rihanna singing Grey's chorus. The song established her as an unlikely hit-maker, one who could induce hip-hop tough guys to drop their guard, and collaborations with Diddy and Dr. Dre soon followed. On one Eminem and Dre track, "I Need a Doctor," she also stepped in as a guest vocalist. "When we recorded that, Eminem was crying in the studio," Grey recalls.

Since then the offers have been flowing in. But Grey, fresh off a European tour with Bruno Mars, is taking another crack at a solo career, with January's Invinsible. The second single, "Invisible," is a swelling, beat-heavy ode to her idle years, but she's not dwelling on her folk-chick flameout—or her rap-fueled rebirth. In fact, the album's first confirmed guest is shock-rocker Marilyn Manson. "I knew people were expecting some kind of hip-hop duet," Grey says. "But I didn't want to do the expected thing."

• • •

Her Greatest Hits (So Far)

"Love the Way You Lie" by Eminem featuring Rihanna
Wrote the chorus of the Grammy-nominated track.


"Coming Home" by Diddy-Dirty Money
Sang on the swelling anthem from Diddy's concept album Last Train to Paris.


"Castle Walls" by T.I.
Crafted the melodious hook performed by Christina Aguilera.


"I Need a Doctor" by Dr. Dre featuring Eminem
Besides performing with the duo at the Grammys, appeared in the video, playing—you guessed it—a doctor.


"Words I Never Said" by Lupe Fiasco
Joined the rapper for a live rendition of the politically charged song on The Colbert Report in May.




Also on Details.com:
Q&A With Skylar Grey
Hip-Hop's Latest It Girl: Rye Rye
Nicki Minaj: Hip-Hop's Hottest Sidekick Goes Solo
60 Seconds With Beth Ditto
Aska: A New Singer With Serious Cred