Vid Pick: Skyler Stonestreet – It Kinda Hurts

Skyler Stonestreet’s name has graced the liner notes of some of the biggest artists of today.

The author of a number of mega-hits, including Dua Lipa’s “IDGAF,” and The Chainsmokers’ “Kanye” (she’s also heard as a vocalist on the latter), as well as songs for Marshmello, Cheat Codes, Austin Mahone, and Sabrina Carpenter, Stonestreet has become known for her work with her pen. With her new post-break up anthem, “It Kinda Hurts,” she about to become known as a solo artist.

Wanting to know more about the Los Angeles-based songstress, I caught up with Stonestreet to ask her about “It Kinda Hurts,” her blow-up doll co-star from the video, and her history of penning hits for big names. She also discussed her unique hairstyle, and the artist that caused her to fan girl out when they met.

Your new single is the post-breakup anthem “It Kinda Hurts.” The lyrics are remarkably detailed, which means you’re either the greatest storyteller in the world, or this song has a lot of real life experience behind it. Tell me about the backstory of the song.

Well, I can’t say too much because then the person it’s about will definitely know {laughs}, but I can say it’s from real life experience.

I wanted it to feel like the story of that night out from start to finish, including all the things that happened, that I imagined, and the complex feelings that happen after a relationship has ended.

The video for “It Kinda Hurts” features you driving around with a blow-up doll riding shotgun. Where is that doll now? Is he deflated and heartbroken somewhere? Give me the Behind The Music of your rebound guy!

My blow-up doll boyfriend is now living at (video director) Jason Koffeman’s house.

He is happy, and rumor has it he has a new boo. 

You and I have something pretty big in common – we’re both cancer survivors! (I’ve been in remission for a year and a half). With that in mind, another interesting aspect of the video for “It Kinda Hurts” is the wigs. Did you develop a fascination with wigs while going through chemo, or was it simply something for the video?

Wow!!! Congrats to being cancer free! I’m high five-ing you through the screen! That’s amazing.

To be honest I’ve always had a fascination for wigs, and trying all kinds of different hair styles, and colors, way before I ever knew I was going to face cancer in my life. But with that being said, I feel like there was a subliminal thing behind it relating to what I went through.


I read you continue to rock the short hair look to inspire young women. What have been some of your favorite reactions you’ve received regarding your look?

I really do love my short hair. I would love it even more if it had been my choice to cut it, but nonetheless I do love rocking the pixie! It’s grown from the shaved head, and today I just went blonde on a whim!

I think all my friends know I am pretty impulsive, so they are not super shocked.

You’ve written for Dua Lipa, The Chainsmokers, and Marshmello, among others. Tell me about an especially awesome collaborative moment from all your time working with other artists.

I love all the artists you mentioned, they are all amazing, and so talented. The second time I played with The Chainsmokers was the craziest show. We were in Orange County and I remember Drew (Taggart) being like, “You’re gonna stand on those risers when you sing,” and I thought nothing of it, until it was time to sing, and the floor was shaking from the bass, there was fog, confetti, and definitely some tequila. {laughs}

I had never been to something like that, let alone sing at it, so it was something I won’t forget.

Those collabs are part of your recent history. Let’s take a minute to dive into your deep history. Tell me about what Skyler Stonestreet was like as a kid. Did you win every talent competition at your school, or were you the quiet poet in the back?

I was definitely the girl talking in every class, writing lyrics on my math homework, and calling my friends to sing them new songs I had written. And I’m still mad I got 3rd in the talent show :)

What were some of the first songs you remember memorizing, and performing, as a kid?

I was classically trained on piano, so I heard a lot of that, but my mom always made sure to play all kinds of different music, from classic rock to Motown, and of course the greats like Carole King and James Taylor.


What idol from your childhood have you had the opportunity to meet, and how did you handle it? Did you manage to play it cool?

I met Rufus Wainwright recently, and that was huge for me. He is truly one of my favorite artists, and voices, and I definitely fan girl-ed out. Didn’t play it cool at all.

Finally, what are you working on now? Are there any collaborations you’re at liberty to talk about? Is an EP, or album, on the way?

I’m working on more of my own music to release, which I’m really excited about, and I’m co-writing with some amazing artists for their projects.

I can’t say much, but I’m really excited to be writing and putting all my energy into music again, there is nothing better!


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