For the past two years, Skylar Grey has been trying to parlay a successful hit songwriting stint with Eminem, Dr. Dre, and Diddy into a solo career. Unknown before 2010, Skylar Grey met producer Alex da Kid through her publisher, and the two began collaborating immediately. The first song Skylar Grey wrote with Alex da Kid was “Love The Way You Lie” for Eminem and Rihanna, which reached number one in over twenty countries. Pretty good for a first try, right?

“Love The Way You Lie” might have been the first song “Skylar Grey” wrote, but it’s definitely not the first song the woman behind Skylar Grey has written. Here’s where it gets interesting. Well, as interesting as a boring-ass, moody piano ballad can be.

Holly Brook (2004-2010)

Before she became Skylar Grey, Holly Brook Hafermann spent her youth performing in a folk called Generations with her mother, and later branched out on her own, dropping the Hafermann and performing as just Holly Brook. At the age of eighteen, Holly Brook moved to Los Angeles and recorded a demo. This recording caught the attention of Brad Delson, the guitar player from Linkin Park, who signed Holly to the band’s now-defunct vanity label Machine Shop Recordings, a subsidiary of Warner. Holly would even appear on the (Linkin Park side project) Fort Minor record, lending her vocals to their hit “Where’d You Go,” which peaked at number four on the Billboard Hot 100, but didn’t give Holly any real mainstream notoriety.

Holly Brook released two EPs and one full-length album of Sarah McLachlan-influenced adult contemporary pop. Though her music did show signs of the moodiness that Skylar Grey would eventually become known for, Holly Brook was at that point relatively unspoiled. You can check out her personal LiveJournal here, which will give you a glimpse at her general optimism before the release of her debut album. Case in point: the most recent entry (2006) in her LiveJournal begins “Animals are the bestest.”

When her album finally came out, Holly Brook didn’t pop off — the closest she got was peaking at thirty-five on the Billboard Heatseakers charts — so Hafermann did what any aspiring musician would do. She killed Holly Brook. Kind of.

Click to enlarge.

The cryptic press release you see above can be found on Holly Brook’s official website, which remains online to this day. The faux-newspaper states that Brook decided to “step away from the industry and head north,” at which point it suggests she would never be heard from again. One can assume that it was posted shortly before Holly’s transformation into Skylar Grey. Skylar delivered a final death blow to Holly Brook in a note to her fans via the Holly Brook Mailing list, citing “recent career changes” for the name change.

Skylar Grey, the tortured, super-serious songwriter and balladeer (2010-2012)

Out of the ashes of Holly Brook was born Skylar Grey, a gothic, sci-fi songbird who was ready and able to craft mournful hooks for pop ballads, like some kind of hip-hop version of Amy Lee from Evanesence. After being paired up with Alex da Kid and signing a deal with his Interscope imprint, Skylar Grey was off to the races, penning hits for Eminem, Diddy, Dr. Dre, T.I., and Lupe Fiasco. In some cases, Skylar would appear as the featured vocalist on these songs, which gave her new persona a very public unveiling. The fact that Skylar Grey exists in a very mainstream world and has no real “cool cache” means that her conspicuous re-branding managed to escape public ire, years before Lana Del Rey would be lambasted for starting from scratch after her Lizzy Grant character didn’t generate results.

After “Love The Way You Lie” conquered the charts, Skylar offered up “Coming Home” by Diddy-Dirty Money, where she was a featured vocalist. Despite being total horseshit, “Coming Home” went double platinum in the United States, and the world was finally introduced to Skylar Grey’s voice. Grey continued to churn out chart-ready ballads, including Dr. Dre’s 2011 single “I Need A Doctor,” which ended up being a one-off, despite claims that it would be the first single from the long-awaited Detox. “I Need A Doctor” peaked at number four on the Hot 100, Skylar’s most successful feature since Holly Brook appeared on Fort Minor’s “Where Did You Go?”

If there was ever a time to test the waters with some solo material, it was now. In August of 2011, Skylar Grey released the Alex da Kid-produced “Invisible” as her first solo single, intending for it to be the title track of her Interscope debut. The song didn’t chart well, and Interscope delayed Grey’s album release. This major label disappointment would have been all too familiar for the former Holly Brook, but the angsty songstress had come too far to start over again.

Skylar Grey, the desperate, newly sexualized version (2012-????)

Over one year later, we’re finally starting to hear from Skylar Grey again. Eminem signed on to executive-produce her debut album, and in a move that seems more desperate than calculated, the first single seems to suggest that Skylar Grey is on the cusp of another reinvention.

Eminem waltzes in, and with the flick of the wrist, a staunchly asexual songwriter who once described herself as “not a very feminine person” has a cheeky, bouncy pop single laden with sexual innuendo. Though Grey could defend it as a satire influenced by an overtly sexualized music industry, no one could argue that she doesn’t stand to benefit from positioning herself as a sex symbol instead of a dark, twisted artist.

To say that it’s a departure is an understatement. “C’mon Let Me Ride” not only reeks of desperation, it’s one of the worst and most disingenuous songs released all year. If it was well-composed and clever, it might be defensible, but Skylar Grey is grasping at straws, trying to make a jump beyond her reach, from moody songwriter to full-fledged pop star. Unfortunately for Skylar, even though Eminem is singing the chorus to Queen’s “Bicycle” in an auto-tuned Pee Wee Herman-esque accent on her “debut” single, it doesn’t mean that the world is ready to stomach her transparent commercially minded reinvention.

There’s still no release date on Skylar Grey’s debut Don’t Look Down. Depending on how “C’mon Let Me Ride” is received, it might be time for Skylar Grey to head north.