Skylar Grey on Redefining Success at 30: ‘I Thought Happiness Meant Having Grammys'

Skylar Grey, née Holly Brook Hafermann, has performed at the Grammy Awards with Dr. Dre and Eminem and garnered multiple Grammy nominations, including one for Song of the Year for Eminem and Rihanna’s “Love the Way You Lie.” She has collaborated with Nicki Minaj, Diddy, X Ambassadors, Marilyn Manson, and more. By all measures of music industry success, the singer-songwriter has enjoyed a bountiful career since releasing her debut album as Grey with 2013’s Don’t Look Down. However, Grey has realized that her definition of success has changed.

“I thought happiness would be being successful in music and having Grammys, stuff like that,” she tells Yahoo Music. “But as I got more successful, I noticed that those moments I thought would make me happy were so fleeting. It would be one day of being really high on top of the world, and then the next dealing with some kind of form of rejection in the industry and being sad again. So I realized I couldn’t base my happiness on my career. I needed to learn how to enjoy the moment more.”

On her new album Natural Causes, out Sept. 23, Grey places a higher premium on having fun. “Maybe it’s turning 30, but I just feel like life’s too short to not have fun — especially since music, to me, is supposed to be fun all the time,” she says. “With this album I basically just wanted to make a bunch of music that I absolutely loved, and I don’t really care what anybody thinks.”

Grey cites the song “Straight Shooter” as a perfect example. “[It] doesn’t necessarily fit the rest of the album, but I love performing it so much, I loved creating it, it’s a really fun song for me.” Another one she enjoys is “Picture Perfect.” “That one, to me, is probably my favorite song on the album, because it’s the first time I really feel like I accomplished a sound that I was striving for for a long time. And that’s that hip-hop drum beat with this almost Bon Iver vocal layering kind of thing. Plus I’m rapping on that one a little bit, which I like doing too.”

Yes, after years of being the featured vocalist on hip-hop tracks, Grey has unleashed her own talent for rapping. It started on the track “Wreak Havoc,” from the Suicide Squad film. Originally that was not intended to be her vocals, but that was what the fates intended. “It’s my first rap song I ever released, and I wrote that ‘cause I thought some rapper would come in and replace my rap,” she says. “So my rap was just a placeholder, and they ended up keeping it and liking it. So it was just like, ‘OK, I guess I’m putting out a rap song now.’”

Grey has had some of the best teachers of all time in rapping working with Dr. Dre and Eminem. The latter produced the single “Come Up for Air.” Though “Em,” as occasionally she calls him, is a friend, she doesn’t lose the sense of wonder whenever she gets to be in the studio with the rap icon. “Any time I get to work with him or whatever, I kind of have to pinch myself and I’m not over the fact I’m working with one of my idols,” she says. “It still blows my mind.”

There is one rap artist Grey has not collaborated with yet that tops her wish list: “I would love to work with Kendrick Lamar though, he’s my number-one dream collaboration for sure.”

Lamar and Grey’s two other favorite artists, Bon Iver and Radiohead, have definitely influenced her own writing on Natural Causes. “My favorite albums to listen to as a music fan are not full of singles, so that’s not really my style of artistry,” she says. “So I would prefer to put out a new album every one or two years, get that thought out and move on to the next evolution.”

This evolution finds Grey concentrating lyrically on getting back to nature. “It’s definitely got a dark tone to it, I think it’s darker than the last album,” she says of the new record. “You can definitely hear my nature influences, which is why I called it Natural Causes. Right off the bat, Natural Causes sounds like a kind of morbid thing to call an album. But that covered the dark side of the album, the way it sounds. There are quite a few death references on the album as well. But the play on words there is everything is caused by nature and so a lot of my songwriting is influenced by the nature around me in Utah [where Grey currently resides].”

The lyrics are also her way of understanding her life. “My lyrics are me psychoanalyzing my own emotions so that I can basically explain to myself what I’m feeling and understand what I’m feeling,” she says. “So, pretty much all the lyrics on my album are a result of me analyzing my emotions and using nature as a sounding board. I compare myself to the wild life around me and how they’re so casual about birth and death and everything in nature just happens and the cycle keeps going. And for some reason humans tend to make everything such a big deal and we get so stressed out.”