Diana Gordon Bares Her Soul In 'Rollin (Acoustic)' Video & Talks Stripped-Back 'Wasted Youth' EP: Exclusive

When pop artists are first introduced as “the next big thing,” it can sometimes feel a bit manufactured. But as they grow older and have real-life experiences, that journey is reflected in the music. In the case of Diana Gordon, she has fervently peeled off a decade’s worth of layers to reveal her true form.

The Queens, New York, native appeared in the middle of last decade’s pop-EDM fusion phase, with former label Atlantic Records branding her as Wynter Gordon. Along with releasing her debut album With the Music I Die in 2011, she beefed up her resume by writing for Mary J. Blige, Jennifer Lopez and Danity Kane.

A few years later, following her Grammy-nominated work on Beyoncé’s Lemonade (“Don’t Hurt Yourself,” “Sorry,” “Daddy Lessons”), Gordon decided to bury Wynter and return to her birth name. She released Pure in 2018, a five-track EP that details her tough family upbringing.

“When you say real-life challenges, I had those at [age] 4,” Gordon tells Billboard. “Even those years where I was making pop music, real life was happening and I wasn’t able to express it.”

She continues: “I watched Shia LaBeouf’s Honey Boy [film] recently. Maybe because it was a woman director [Alma Har’el], it was so incredible. Each scene had so much emotion. I was like, ‘Damn, I understand him now!’ Holding that in was really hard — that’s how I got anxiety. You smile and act like it’s all great, but it wasn’t. [whispers] I’m Honey Boy.”

When those feelings are bottled up for so long, that cap will explode without warning. Now, Gordon is wiping off the metaphorical clown makeup to share her innermost thoughts on new EP, Wasted Youth. Released Friday (April 3) via Warner Records, the singer reflects on a once-volatile relationship and various phases of maturity.

Standout tracks include “Once My Friend,” which is a ripped diary page come to life, and the acoustic version of thumping rager “Rollin,” whose video is premiering exclusively on Billboard:

Below, Gordon speaks to Billboard about breaking toxic love cycles, her admiration for ‘90s alternative singers, and why her musical journey is just beginning.

We’ve known you as Wynter Gordon for so long, and now you’re going by your true name, Diana Gordon. 

I wouldn’t say it’s my “true self” because honestly, I’m still discovering parts of me and what I don’t want in my life. It’s all experimenting and I’m still a kid — in my heart! I was really young when I was given that name by my management. All the things that I learned about what I don’t want from the business … I had built such a huge following as Wynter, but it was hard for me to experiment once I came into my own. Not just as a musician, but as a person.

So in order to have the freedom to find myself, I had to be myself. A lot of my fans loved dance and they wanted to hear EDM, and that really wasn’t what I was trying to do anymore. So I just switched! I think in the future, I’m going to put out nameless, faceless projects. I’m going to work without people even knowing that it’s even me.

We’re both New York City girls, and now you’re in Los Angeles. Did moving away from the city’s ruggedness influence your music?

Before I left New York, I was living in Brooklyn next door to a foster home with a lot of kids. I had the worst anxiety, where I ended up in the hospital and I really just needed a change. I moved to L.A. so I could be on a quiet street and find some peace. I rented a house and built a studio in the basement — that’s where I wrote Pure.

I found my [older] brother when I moved to L.A., and that was the catalyst of Pure to happen. He was missing for 16 years at the time. I found him on the street on my way home, and that was such a healing thing I needed to have.

It sounds like the universe was trying to tell you something, as if you were meant to go to L.A. for that moment.

I’m very spiritual and I believe there are signs everywhere. The music that I’m putting out now, I wrote a year and a half ago. I felt like nothing was going right and I was making the wrong decisions. I got into an Uber [recently] and there was a ’60s song playing and it said: “I love you, Diana.” Sometimes I’ll step on a sticker and it’ll say “Diana.”

I’ve found myself in moments of hesitations where I feel like I’m not on the right path. And then the universe or the spirit angels send me a sign. No matter what wrong turn you take, you’re gonna get right back on. I have to know that I have a purpose, whether it be touching my brother’s life or even your life, Bianca. I might be the lesson that someone greater than me needs.

When I first heard this new EP was titled Wasted Youth, it was like looking in a mirror. Do you have any regrets when it comes to past relationships?

Definitely. [laughs] There was a big relationship that I had — I don’t know if I should even call it a relationship. It was time I wasted listening to someone else and letting him have power over me. Your early 20s are your exploring years, and I didn’t get to explore who I was until later on in my life.

As much as I want to say I don’t have regrets, there are some men who you have to completely let go of. I remember seeing a certain person who I dated for almost 10 years on the street, and we walked by each other without even saying a word, as if we were ghosts. So Wasted Youth kind of sums it all up.

Is it painful to relisten to these songs?

Sometimes when I perform them, those feelings come out. But not when I listen to them. I’m the type of artist that will talk about a situation in a song and never feel like I truly got the emotion out. So I’ll try to bring up that same person on the next album, but in deeper detail. I don’t always get out those feelings [completely].

You previously told me that Tracy Chapman and Alanis Morisette were influences for this record.

I tried to experiment mixing trap music with my vocals, which are inspired by [those singers], The Cranberries and Joni Mitchell. I wanted to find my true sound that would be super consistent, and bring that alive with the melodies. Like the “try, try, try” part in “Wasted Youth” is very alternative girl [sounding].

It’s refreshing to hear a millennial black girl go completely left and experiment with alternative music.

I feel like I can do any genre. I’m a ’90s R&B girl, but I can get into my New York hip-hop moments. But what resonates with me the most as a singer is the alternative, eerie, yodel-y, ethereal vocal.

Speaking of eerie, you have two very different versions of “Rollin” on this EP. You told me before that you wanted it to feel like The Isley Brothers’ “Shout.”

I wanted the feeling where people can jump up at my live shows. So when we play it and add the drums, it really feels like a church service — like that standard black Baptist church that I grew up in, that shoulder shrug type of feeling with the pastors going down the aisle, like Whoopi Goldberg in Sister Act.

“Rollin” was actually the last song we decided to put on the EP, but it’s the first song that’s coming out. I shot three videos for the original song, and this was footage that was left over from one of the videos. So I decided to put it for the acoustic version. It’s kind of like the black Trainspotting. It’s about real, true friendship: You see their interactions and everyone has a character. You can feel the bond between them and it was something that felt good to me.

The acoustic version really shows your artistry. It’s literally just you and the guitar.

I would love to do that more. I haven’t really unleashed the beast of my voice yet on a recording. When you see me at a live show, you’ll be like, “Goddamn!” I’m still learning to give that same feeling that I have [while singing live] when you put the earphones on. I tried to be as bare as possible on the “Rollin” acoustic.

There’s a standout line on “Tell Myself”: “I got the whole universe to go find someone/ End up with the usual suspects.” Was there a moment where you figured out how to break that cycle?

Hell yeah! [laughs] Let’s just say I was in Jamaica with a guy and he was just acting up. I told myself, “Nuh-uh, I’m not doing this ever again.” I always date guys who are my muses, who force me to write songs about them. But those aren’t the most healthy relationships. The passion doesn’t always come from the romance — it comes from the anger and heat from the fighting. When you look in the mirror and say, “Why am I not good enough?” Once that question comes up, you’re not in the right relationship.

“Once My Friend” is my favorite song. No matter how destructive your relationship was, you still find some strength to move on and forgive them.

Forgive, but never forget! [laughs] I got to that point when I went to his Instagram — when I was stalking a tad bit — and I could look at his photos without feeling like my heart was gonna stop. I’M fine, and I wanted him to be fine. That was a big step for me and it took years. I don’t harbor any feelings of revenge, you know? That dissipated. I’ll add you in my prayers sometimes when I’m feeling genuine. And that’s one of the most classically written songs I’ve ever done. I wrote that one with one of my favorite collaborators, Rob McCurdy, who goes by MOSSS. The songs that people love the most from me, like [Pure tracks] “Wolverine” and “Kool-Aid,” he’s done the production on.

On the title track, you sing “I f–kin’ wasted youth/ But I’m blessed too blessed to be angry for it.” Was writing that song therapeutic for you?

That time was wasted, but I sure did f–king make up for it. I traveled the world, met beautiful people, worked with Beyoncé and Dev Hynes and all these great artists who I’ve looked up to. I didn’t let this hold me back despite all the obstacles, and I’m proud of myself for moving past the pain. And that’s a blessing, because some people crumble.

I know you’re still sitting on a mountain of unreleased music. Have you thought about how you want to roll out the next projects?

I wanna get my Miseducation of Lauryn Hill on and just get really personal with my life lessons. Lauryn did it the best. She put what she went through in plain [sight] for all of us to see and left nothing out. I don’t think I’ve told my story verbatim where you can really put it to paper. You kind of have to decipher it.

Where I would like to go next is vocally holding nothing back. I want people to know that I stand with the greats with my voice. With my story, I want you to see that I’ve been my own personal hero and have people respect that. I want it to be my swan song, because I’ve been doing this for a very long time and that’s what I deserve for myself.

This interview has been edited and condensed for clarity and length.