In 2004, at the age of 17, Grey signed a publishing deal with Universal Music Publishing Group and a recording contract with Machine Shop Recordings under the name Holly Brook.
In 2006, she released her debut studio album Like Blood Like Honey, under the aforementioned labels.
The album reached the top 10 in the US and produced four singles.
Grey wrote the hook to all three versions of "Love the Way You Lie" by Eminem and Rihanna, and even recorded a solo version that was later featured on her fourth EP, The Buried Sessions of Skylar Grey (2012).
"I Need a Doctor" managed to peak at number four on the US Billboard Hot 100 chart and was certified double platinum by the RIAA.
Skylar Grey made her national television debut under her new alias during the 53rd Annual Grammy Awards, where she performed "I Need a Doctor", alongside Eminem and Dr. During this time, Grey announced she began working on her album then-titled Invinsible.
In March 2011, it was revealed Grey signed to Interscope Records, through Alex da Kid's KIDina KORNER and announced she would be releasing a single in the spring.
Grey released her debut single, "Dance Without You", on June 6, 2011.
Grey's second single and formerly her second album's title-track, "Invisible", was released to radio on June 16.
Grey went to New York to meet her publisher Jennifer Blakeman, to seek help presenting her work.
Blakeman had suggested that she work with English musician and record producer Alex da Kid. Alex da Kid sent Grey a few tracks that he had been working on.
Their version became a worldwide hit, reaching number one on 26 charts and being nominated for four Grammy Awards.
Grey earned a Grammy nomination for Song of the Year, for her writing contributions to "Love the Way You Lie".
Played Herself - Guest in "Last Call with Carson Daly" in 2002. Played Herself - Musical Guest in "The Colbert Report" in 2005. Dre Said Is He Looking To Record A Few More Tracks With Snoop Dogg. The song is a single from Diddy's most recent album entitled "Last Train to Paris" and was released as a single in November of 2010.