Born Holly Brook Hafermann in Mazomanie, Wisconsin in 1986, Grey began singing as a toddler. An early love of folk and jazz led to a strong affection for the music of Joni Mitchell, and she performed as half of the folk duo Generations with her mother, Candace Kreitlow, from her preteen years into high school. The mother-daughter act released three albums via Heartwood Productions between 1996 and 2002, usually credited as Holly Brook and Candy K.
Having developed her singer/songwriter-influenced pop songwriting throughout her teens, she moved to Los Angeles in 2003, where she met Grammy-winning producer Jon Ingoldsby. Still going by Holly Brook, she signed with Universal Music Publishing Group and Machine Shop Records and wrote two songs with Ingoldsby for actress Brie Larson's album, Finally Out of P.E. It saw release in 2005. That same year, she was the featured singer on two songs by Fort Minor, the genre-bending hip-hop project of Machine Shop label runner Mike Shinoda of Linkin Park. One of those songs, the single "Where'd You Go," reached number four on the Hot 100. As Holly Brook, Grey released her first solo album, Like Blood Like Honey, in 2006. It cracked the Top 40 of Billboard Heatseekers Albums chart. Meanwhile, she embarked on tours opening for artists, among them Jamie Cullum, k.d. lang, and Duncan Sheik.
After parting ways with Machine Shop, Grey continued to take writing sessions, and she was eventually featured on tracks by rapper Apathy that appeared on the 2009 album Wanna Snuggle? That same year, she joined Sheik's touring band and contributed to his Whisper House LP. Sheik and Ingoldsby co-produced her 2010 release, O'Dark:Thirty EP. Brook then adopted the professional alias Skylar Grey.
As Skylar Grey, her first collaboration was with English songwriter/producer Alex da Kid. Their song "Love the Way You Lie" made its way to Eminem, who did a version with Rihanna that became a worldwide hit, topping the Hot 100 and earning Grey, Alex, and Eminem a Grammy nomination for Song of the Year. Grey recorded a solo version of the song that appeared on her 2012 EP, The Buried Sessions of Skylar Grey. It was released by Alex da Kid's Interscope imprint Kid Ina Korner.
As she went to work on her Skylar Grey long-form debut, she was featured on a variety of recordings, including hit singles by Diddy - Dirty Money ("Coming Home") and Dr. Dre ("I Need a Doctor"). She performed a medley of the latter song and "Love the Way You Lie, Pt. 2" with Dre, Eminem, Rihanna, and Adam Levine at the 2011 Grammy Awards. Later that year, another writing collaboration, Lupe Fiasco's "Words I Never Said," featured Grey, leading to a performance with the rapper on TV's The Colbert Report.
Grey issued her debut single, "Dance Without You," in June 2011. It was later included in the 2012 film Step Up Revolution. That year's "C'Mon Let Me Ride" -- produced by Alex da Kid and featuring Eminem --reached Canada's Hot 100. The year 2013 saw the release of songs she co-penned for Cee Lo Green ("Only You") and will.i.am ("Love Bullets") before Grey's full-length debut, Don't Look Down, arrived on Kid Ina Korner. With guests including Eminem, Big Sean, and Travis Barker, it peaked at number eight on the Billboard 200. In 2014, the 2012 release "Clarity" by Zedd featuring Foxes, which Grey co-wrote, won a Grammy for Best Dance Recording. That year, she also sang on Moby's "The Last Day" and landed on the dance charts with a guest spot on David Guetta's "Shot Me Down." Continuing to work on her own music, write with others, and make high-profile guest appearances, she reached the U.S. Hot 100 as featured vocalist on the late-2014 Nicki Minaj single "Bed of Lies" following a performance of the song with Minaj on Saturday Night Live. Around that time, she also had a Top 20 dance/electronic hit with Guetta's "Rise."
In mid-2016, Grey contributed a pair of tracks to the Billboard 200-topping Suicide Squad soundtrack, including her own "Wreak Havoc" and a songwriting credit for Kehlani's "Gangsta." That September, her sophomore album, Natural Causes, arrived via Kid Ina Korner. With Eminem contributing, it peaked at number 68 in Canada. In October, her vocals were featured on "Beneath with Me" by Deadmau5 and Kaskade.
Grey made her sixth appearance on the Hot 100 with a featured spot on the 2017 Macklemore single "Glorious," which peaked at number 49. A year later, her song "Everything I Need" was included on the soundtrack for Aquaman. Grey left Kid Ina Korner before releasing the independent EP Angel with Tattoos, in 2019. A second independent EP, Make It Through the Day, arrived in November 2020. In 2021, she contributed the song "Last One Standing" (featuring Polo G, Mozzy, and Eminem) to the Venom: Let There Be Carnage soundtrack. ~ Marcy Donelson, Rovi
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