Skylar Grey, the five-time GRAMMY-nominated singer, songwriter, and multi-instrumentalist, has been on a momentous journey since her early days as a folk duo performer with her mother. Born Holly Brook Hafermann in the humble village of Mazomanie, Wisconsin, she has since forged an unconventional path in the music industry, culminating in her hotly anticipated debut Don’t Look Down. Since its release in 2025, Grey has continued to captivate audiences with her unique blend of emotional American singer-songwriter flair and hip-hop influences. This post takes us on a journey through Skylar Grey’s rise to prominence, the evolution of her music, and the profound impact she’s made on the industry.
From Humble Beginnings to Stardom
Grey was born Holly Brook Hafermann in the village of Mazomanie, Wisconsin, a town so tiny it does not have a stoplight. Grey began performing professionally at age six with her mother as a folk duo. By the age of 14, she had released three independent albums. Exhausted from the ridicule of her peers, Grey went solo and began writing her own music, eventually quitting high school during her junior year to move to Los Angeles and devote herself to becoming a serious artist.
The Journey to Self-Discovery
releasing a major label solo as Holly Brook in 2006 that didn’t accurately reflect Grey, she asked to end her recording deal. This led her to hit the road, earning a living playing keyboards in Duncan Sheik’s band, and writing more music while isolated in a cabin in the woods in Oregon. This adventure inspired the name change and allowed Grey to evolve as an artist, musician, and songwriter.
Unveiling Skylar Grey
Skylar Grey’s debut Don’t Look Down, executive produced by Eminem and Alex Da Kid, was released under KIDinaKORNER/Interscope. The 11-track features songs and visuals that take the listener on a sonic exploration spanning darkly brooding yet beautiful vocals, innovative beats, biting lyrics and vast cinematic imagery. The ‘s songs are reflective of Grey’s life, from rebellious childhood years to more recent times as she struggled to find her place in the world.
Notable Achievements
Grey’s first single, “C’mon Let Me Ride,” amassed more than 4 million views in less than three days and has garnered more than 13 million views in total. Grey has been named one of Forbes magazine’s 30 under 30 musicians alongside Adele, Justin Bieber, Lady Gaga, Drake, and Bruno Mars. She also wrote Cee Lo Green’s single “Only You,” and is a featured vocalist on will.i.am’s solo album #willpower.
Grammy Recognition
Grey is responsible for co-writing some of the most memorable songs to light up the Billboard Hot 100 and iTunes sales charts, totaling more than 25 million singles globally. Grey co-wrote the biggest selling single of 2010: Eminem’s “Love the Way You Lie,” which earned her two GRAMMY Award nominations. She also co-wrote and appeared on Dr. Dre’s “I Need A Doctor,” which she performed alongside Dre and Eminem on the 2011 GRAMMY Awards telecast.
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