A pop singer with recognizably breathy, earnest vocals and a songwriter in demand for her big-chorus hooks, Skylar Grey co-wrote hits for the likes of Eminem ("Love the Way You Lie") and Zedd ("Clarity") before reaching the Billboard 200 Top Ten with 2013's Don't Look Down, her solo debut under the Grey moniker. Still incorporating shades of hip-hop, 2016's Natural Causes was marked by heartfelt lyrics and a more atmospheric sound. She has continued to mature, issuing two independently released EPs with 2019's Angel with Tattoos and 2020's Make It Through the Day. In 2021, Grey cracked the Hot 100 with "Last One Standing" (featuring Polo G, Mozzy, and Eminem) off the Venom: Let There Be Carnage soundtrack. Following a four-year legal battle with her ex-husband and former manager, she marked a new chapter in her life and career with her first independent album, 2022's Skylar Grey.

Born Holly Brook Hafermann in Mazomanie, Wisconsin in 1986, she 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, Hafermann 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, Hafermann 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 such as Jamie Cullum, k.d. lang, and Duncan Sheik.

After parting ways with Machine Shop, she continued to take writing sessions and 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. The 2012 release "Clarity" by Zedd featuring Foxes, which Grey co-wrote, won a Grammy for Best Dance Recording in 2014. 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. Also that year, Grey finalized her divorce from her ex-husband and former manager, a deal that found her selling her publishing catalog to settle her legal bills. She re-emerged in 2022 with her fourth album and first independent release, the eponymously titled Skylar Grey. ~ Marcy Donelson, Rovi