Hit maker Skylar Grey remembers her Madison-area musical roots

Her big break came from co-writing “Love the Way You Lie,” the Eminem hit (featuring Rihanna). Grey can be heard singing on Dr. Dre, Nicki Minaj and Macklemore records, too.
Skylar Grey sitting in a chair with horns around her
Skylar Grey Photo courtesy of TCB PR

Since growing up in Mazomanie, performing as a child in a folk duo with her mother and moving to LA as a 17-year-old in 2004, Skylar Grey has gone on to write songs and hooks recorded by artists you might have heard of before, including Beyoncé, Alicia Keys, Christina Aguilera and Celine Dion among others. Her big break came from co-writing “Love the Way You Lie,” the Eminem hit (featuring Rihanna). Grey can be heard singing on Dr. Dre, Nicki Minaj, Macklemore and Train records, too.

Grey’s success, particularly as a sought-after hip-hop collaborator, tends to overshadow her solo work — such as her new EP “Angel with Tattoos” — and her diverse musical background, first cultivated in the Madison area.

Born Holly Brook Hafermann, she performed with her mother, Candace Kreitlow, in the duo Generations as a child. They toured the Midwest extensively and recorded three albums in the Cottage Grove studio of Randy Green. At the age of 10, Hafermann started working with local children’s entertainer Ken Lonnquist, performing in his musical production “The Legend of Old Befana” and singing on several of Lonnquist’s records at the time.

Grey spoke with Madison Magazine in October shortly before the independent release of her fourth solo project, the five-track EP “Angel With Tattoos.” Here is an edited Q&A with Grey.

You’ve worked with some of the biggest names in music. But can you name-drop some of the people in the Madison area you worked with growing up?
Someone who had a significant influence on me as a youngster was Ken Lonnquist. He taught me a lot about being a performer. He’s really animated and a really good songwriter. We were definitely pretty tight back in the day. Then as I grew up I was like, “Mom, my peers don’t think it’s cool for me to be singing kids’ songs.” As I became embarrassed about that, I got into pop music and writing my own music. When I was 6 I played an original tune. But I didn’t start writing lyrics until I was about 10. At age 14 I told my mom I was going solo.

When you were a teenager you snuck into clubs and bars to play with local jazz musicians.
Yes. I started out doing a little bit of jazz, sitting in and singing some jazz standards and stuff. But for the most part I saw these incredible musicians and an opportunity to put together a band. And Jeff Eckels [best known as the bass player on “Whad’Ya Know,” the formerly syndicated public radio quiz show] really helped me do that and play my own original songs. That was my goal.

When I put my first band together, it included Eckels and Tim Whalen [who became keyboardist and vocalist for Phat Phunktion]. I was still trying to figure out my sound, though. I had these songs that were definitely not jazz and we tried to make it all work. It was experimental, definitely.

We’d been playing together awhile when Tim Whalen said something to me that was really powerful. He said, “If you can play your own instrument and sing, that would set you apart from a lot of the other singers.” I was writing and playing on the piano but I was too afraid to perform on the piano while I sang. Him saying that was a huge thing for me. And to this day the best performances I have, that go over the best, are when I’m sitting at the piano and singing my own songs. Another person who was very inspirational from the Madison area was Leo Sidran. He helped me record some of my songs. We worked together for a little bit before I moved to LA.

You were 17 when you dropped out of Wisconsin Heights High School and moved to LA. Did you go alone?
Yeah, my mom helped me get out there but she didn’t move with me. I spent my college savings basically on recording demos and stuff and living and surviving in LA. I got my first record deal about a year and half after I moved out there.

And that was as Holly Brook. How long did you keep that identity and persona?
My last name, Hafermann, was just not “rock star” enough. And hard to say and spell. You always want to make it easier for people. So I went by Holly Brook for a while. I had my first hit [in 2006] singing on “Where’d You Go” by Fort Minor [hip-hop side project of Linkin Park member Mike Shinoda]. That song was super successful but I wasn’t really prepared to follow it up with my own music. I had my own music [Warner Bros. released “Like Blood Like Honey,” Brook’s debut album, in 2006], but it wasn’t quite what it needed to be. I learned about the brutality of the music industry at that point. I lost my record deal, my management, my lawyer and went broke. Suddenly I was questioning why I had chosen to do music in the first place.

Moving out to LA, I’d been put in these rooms with all these different producers and having record companies that tell you what they think you should do, what you should look like, what your music should sound like. It became more of a priority to succeed than to make music I was proud of. I became lost in that and was making music I didn’t even like.

So I moved away to a cabin in the woods in Oregon just to find myself again. I disappeared for a while and fell back in love with music when I wasn’t surrounded by anybody’s opinions but my own.

I started playing piano and singing backup for Duncan Sheik, went on tour with him for a few years. Even though I loved it and had a lot of fun, I realized I wanted to be center stage and play my own music. So I called my publisher. She was the only person I had left in my corner from the Linkin Park days [when I was] signed to a label. Everybody else had disappeared. But I was still under contract with UMPG [Universal Music Publishing Group]. She told me that there were a lot of up-and-coming producers making hip-hop beats and rappers who needed hooks. And I was like, “Hooks are easy. I can do that.”

So my publisher introduced me to a producer named Alex da Kid. We met over email. He was living in New York and I was still in this cabin in the woods. And I wrote and recorded the hook to “Love the Way You Lie” and sent it back to him over email. I knew he was pitching it to Eminem but I didn’t really believe it would get to him, I guess. I was just, like, “Whatever. I’m going to take a shot at this.” It got to Eminem. Eminem loved it, recorded it in Detroit and then had Rihanna sing it, and she was in Dublin. So none of us were in the same room together. Then it came out about a month later and was a No. 1 song. So I got thrown back into the music industry in a big way. I had so many people calling to try to get me to write a song for them. Puff Daddy, Dr. Dre, T.I., Lupe Fiasco. Lots of rappers.

You didn’t bring a background in hip-hop collaboration with you from Wisconsin. That wasn’t in your musical DNA, was it?
It was not in my DNA. I was listening to Eminem, but hip-hop was definitely not part of my lifestyle. But getting to work with Eminem, I suddenly got thrown into this hip-hop world. But I think that’s kind of what made it cool and appealing to people, that it was something different I was bringing. These hooks were coming from a singer-songwriter. And if you took the hook off the hip-hop track, it could be a country song, it could be a pop song.

Huge artists can and have made hits out of your songs. While that must be very satisfying, I imagine you’d like to be recording them yourself and having just as much success with them.
There’s definitely an inner struggle when I give a song away. But then I also think, “How lucky am I that I get to write songs for Rihanna, Beyoncé, Pink and Alicia Keys?” These are people I’ve looked up to my whole life, and I’m so grateful for the opportunities to work with these legends, you know? But yes, there’s always something eating at me inside. I know I can make a living writing songs for other people. I don’t know that I can make a living just being an artist. So I stick to what’s safe and what will pay the bills. To take the risk to focus on being an artist and keep all my songs [would be] a scary move to make in my position. But that’s probably what it’s going to take for me to have the success as an artist that I want. I’ll have to be more precious about my songs.

In an email about your new album, “Angel With Tattoos,” you said it is an homage to the music you had grown up with. You can definitely hear Fleetwood Mac in “Shame on You,” the first single.
And [on other songs on the album] Carole King and Joni Mitchell — people that inspired me as I was growing up and listening to my mom’s records. That’s not the sound I’m going to do forever. I grew up with such an eclectic musical background from all the theater I did, my mom being a Celtic harpist [and multi-instrumentalist] and my dad [Gene Hafermann] being in a barbershop quartet. So my influences are all over the map. I’m a chameleon and I can’t stay in one genre.