On December 11, 2012, Grey released her album's lead single "C'mon Let Me Ride", which was produced by Alex da Kid and features Eminem, via digital distribution.The single was later serviced to radio on January 15, 2013.Grey's second album, Don't Look Down, was released in July 2013, and her third and most recent one, Natural Causes, on September 23, 2016.Together, with producer and engineer Randy Green, they independently produced three albums, Dream Maker, Lift Me, and Millennial Child / Waiting for You.In 2006, she also released her debut album, Like Blood Like Honey, under the aforementioned labels.In 2010, she co-wrote Eminem and Rihanna's hit single "Love the Way You Lie", alongside Eminem and British record producer Alex da Kid, who subsequently signed her to his label imprint, KIDina KORNER.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.Later in 2011, Grey was featured on a song titled "Words I Never Said", the second single from Lupe Fiasco's Lasers (2011).
The first song Grey wrote was "Love The Way You Lie".
"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 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.
Grey's second album, Don't Look Down, was released July 5, 2013.