Skylar Grey Writes Your Favorite Rap Songs, Then Makes Them Even Better

Hey Pop Think-ers! I’m Sam Lansky, and my favorite part of any rap song is the part where a female singer belts out a catchy chorus. In my fervent study of the hip-hop hook, I’ve come across few songbirds as talented as Skylar Grey, the mysterious singer-songwriter who came into the public consciousness in 2010 singing the haunting melody on Diddy-Dirty Money‘s “Coming Home” and penning monster hits such as “Love the Way You Lie” for Eminem and Rihanna before releasing her own debut single, the moodily gorgeous “Invisible.”

Now, with the release of her new EP, The Buried Sessions of Skylar Grey, Skylar is giving the public a taste of what chorus-conscious pop fans like myself have been craving: the original versions of three of her finest tracks, including “Coming Home” and “Words” (later reimagined as “Words I Never Said” for Lupe Fiasco), as well as her stunning demo for “Love the Way You Lie.” It’s an impressive showing from an artist who is better known for crunchy rap hooks than for her stripped-down acoustic balladry — and this week, I’m taking a look at how Skylar’s unparalleled versatility makes her one of the most promising artists in the game.

When Skylar Grey first charted at No. 1 with her spot on Diddy-Dirty Money’s “Coming Home” late in 2010, few casual listeners realized that it was actually her second time hitting the Top 20: The first was as the featured vocalist on Fort Minor‘s 2006 smash “Where’d You Go,” under her previous identity Holly Brook. As Holly Brook, Skylar (whose birth name is Holly Brook Hafermann; confused yet?) released a pair of singles and an album, Like Blood Like Honey, all of which underperformed commercially.

But she kept on trucking, teaming up with the tremendously talented pop-rock composer Duncan Sheik, best known for his 1995 radio hit “Barely Breathing,” on a number of projects. (An aside: Duncan Sheik wrote the music for the famed musical Spring Awakening, in which the female lead was first played by Glee‘s Lea Michele on Broadway — small world, right?) As late as 2010, though, Skylar was still releasing music under the name Holly Brook; her last EP as Holly, 2010′s O’Dark:Thirty, is spare and haunting, and even if the hooks are sharply crafted and catchy, they probably wouldn’t be described as “pop.”

But simultaneously, Skylar had also begun work with Alex da Kid, the producing wunderkind known for B.o.B.‘s Hayley Williams-assisted mega-smash “Airplanes.” Together, they collaborated on a series of hip-hop singles: “Love the Way You Lie,” T.I. and Christina Aguilera‘s “Castle Walls,” and finally the Jay-Z produced “Coming Home,” the first single to feature Skylar’s vocals with her new pseudonym. (Alex da Kid is also producing the entirety of Skylar’s debut album, Invinsible, due out this year.)

+ Read more about Skylar Grey’s versatility after the jump.

At the start of 2010, she was Holly Brook, a husky-voiced singer-songwriter writing songs in the remote forests of Oregon and independently releasing an EP in the vein of Ingrid Michaelson or Sarah McLachlan; by the end of 2011, she was Skylar Grey, a Grammy-nominated songwriter with a No. 1 hit who had collaborated with the absolute crème de la crème of hip-hop’s elite: Eminem, Diddy, Jay-Z, T.I., Lupe Fiasco and the grandaddy of them all, Dr. Dre, who teamed up with Skylar and Eminem for his single “I Need a Doctor.” Despite this, Skylar has, I think, remained something of a cipher in the public eye: In the video, Skylar plays a nondescript doctor waiting bedside for Dre, while an ethereal model mouths the words to Skylar’s hook. And when Skylar, Dre and Em performed the track at the 2011 Grammys, Skylar’s face was almost completely obscured. Istill helped build buzz (at least, she trended on Twitter), but perhaps more in keeping with her original artistic sensibilities, Skylar’s been relatively self-effacing, getting her name out there more than her face. Still, her transformation from stripped-down chanteuse to rap collaborator has been a dramatic one.

Part of this evolution, of course, is due to Alex da Kid’s unique production style, since he’s become well-regarded for hip-hop that transcends genre boundaries, especially utilizing influences from alternative rock and ambient pop; this makes him an ideal collaborator for Skylar, given her diverse background and rock sensibility (she has a track with Marilyn Manson on her debut). But it’s also a product of the fact that Skylar writes some of the most crushingly beautiful and sad songs of anyone currently working in the industry, with a vulnerability that’s almost bracing, songs that work marvelously as the centerpiece around which hip-hop anthems are built, but are also remarkable in their own right.

That’s exactly what she’s showcasing on her digital EP, The Buried Sessions of Skylar Grey, released on Jan. 17, which offers the original versions of “Love the Way You Lie,” “Coming Home” and “Words I Never Said.” Her demo of “Love the Way You Lie,” christened “Part III” here, since Rihanna released her own “Part II” of the track as an understated piano ballad without Eminem as a bonus track on Loud, is dark and lovely; the full version of “Coming Home” is triumphant yet delicate, with revealing lyrics. “And the blood will dry underneath my nails/And the wind will rise up to fill my sails/So you can doubt/And you can hate/But I know/No matter what it takes/I’m coming home.”

The most powerful of all, though, is “Words,” which Skylar told Rap-Up was written about not getting to say goodbye to her grandfather before he passed away. “Always in a rush/Never stay on the phone long enough/Why am I so self-important?” she asks over a lonesome piano and warm chords. Her haunting vocals transform the song into an elegiac dirge. “Said I’d see you soon/That was all maybe a year ago/Didn’t know time was of the essence.” Whereas Lupe’s “Words I Never Said” was a song about political conflict and social stratification, Skylar’s version is more intimate, a song about grief and regret. In both versions, though, the songcraft is evident.

Because, as hip-hop has opened up to receive artists from other genres and vice-versa, Skylar has found her place in the industry, even if it took a few false starts and reinventions — and it’s right here, at the unlikely intersection of the serious singer-songwriter and the girl singing the hook on a rap song. The boundaries between genre are becoming blurrier than ever, which allows space for an artist such as Skylar Grey to team up with hip-hop’s A-list for tracks that are unexpected and exciting. And why not? The songs are brilliant. Not a whole lot else matters.

Sam Lansky is a writer and editor from New York City. He goes hard for Swedish pop music, “Real Housewives” GIFs and juice. Follow him on Twitter or Tumblr.