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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.The first song Grey wrote was "Love The Way You Lie".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.

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She has worked with songwriters such as Nathan Chapman, Brett James, Hillary Lindsey, Luke Laird, and Chris Tompkins.

She also debuted an original song called "Settle Down," written by herself, Chris De Stefano and Anne Preven.

In August 2009, still under the alias Holly Brook, she lent both her song "It's Raining Again" and her image to a promotional campaign for Ciao Water. She was still living in Oregon and had no recognition as Skylar Grey.

Grey went to New York to meet her publisher Jennifer Blakeman, to seek help presenting her work.

In the semi-finals she performed "Stay with Me" by Faces.