Much like the rest of the world, Olivia O’Brien’s original plans for 2020 were completely derailed during that now-infamous mid-March week when most of the U.S. was plunged into quarantine due to the COVID-19 pandemic.

She was in the middle of her It Was a Sad F---ing Tour, the name of which proved a bit more literal than expected, when she was forced to postpone it indefinitely. Once the tour was finished, she had planned to release a couple of new songs, make her Coachella debut and move onto her next project. Instead, since then she’s spent most of her time inside.

“I honestly haven't been creative at all during quarantine,” the 20-year-old singer admits. “I mostly write about either being sad or relationships, dating and love, and all of that stuff, so I haven't really been experiencing any of those things.”

However, when her anti-cheater anthem “Josslyn” unexpectedly blew up back in May thanks to a TikTok dance challenge that helped the track amass over 70 million streams worldwide, her career picked itself back up full-force. Her current creative block hasn’t been too much of a hindrance thanks to the many, many songs sitting in her Dropbox awaiting release.

The first to see the light of day is the bombastic “Now,” which dropped Friday (September 18) alongside a vibrant music video jam-packed with 2000s pop culture references and cameos from some of famous friends including Devon and Sydney Carlson, Lukas Abbat, Alexandra Cooper and Quen Blackwell, among others.

The day of its release, O’Brien hopped on a Zoom call with PopCrush from her Los Angeles home to chat about sampling Akon, upcoming album plans, her debut smash “i hate u, i love u,” and more.

Can you share the process behind the creation of "Now"?

Basically, as soon as you listen to it you hear that it's a flip of Akon's song "Right Now," which was probably one of my favorite songs growing up. The writer that I made it with, it was actually her idea. She was like, "How cool would it be if someone flipped this and turned it into a breakup song?" As soon as she said that I was like, I'm so down.

I'm obsessed with that song, so I felt like it was kind of perfect, but we didn't want to completely rip it off. I know that some people will remake songs and use the production and everything, but I just felt like it'd be more fun to go in a different direction. The verses aren't the same melodies at all, so we pretty much just ripped the hook melody. I feel like it has the perfect amount of nostalgia while still being new.

“Right Now” came out when you were eight years old. What are your memories of that song?

Well, I definitely didn't know what it was actually about. I don't think I knew what "making love" was. I was probably like, "Yes, go off." It gives me the same vibes as "Dynamite" by Taio Cruz and all of those types of songs that I was just obsessed with. It's just super fun. I feel like any song from that time in my life, the early 2000s to maybe 2011, just gives me such nostalgia for my childhood, and everything I've been doing for the past few projects has been very nostalgia-based.

I actually found a post that I posted on Instagram in 2018. It was the new year, and I was like, "I want to become the person that I was when I was a little kid," because I was amazing when I was a little kid, and I think I lost that magic. I feel like when you're a little kid you don't have people telling you like, "Oh, you can't do that," or "you suck" and whatever, and as you become a teenager, that's when the bullying really happens. People tell you, "Oh no, you can't be a singer. You can't do that.”

I really let that get into my head when I was a teenager, and it kind of messed me up, so I'm trying to make my 7-year-old self proud and emulate the icons that I used to look up to when I was a little kid.

Maybe it's a reach, but have you thought about trying to get Akon on a remix?

Oh, I'm trying. I'm trying my darnedest, but he is currently in Africa in Akon City. He has his own city now, so he's been a little bit hard to reach. We've gotten close a few times. I actually had my label reach out. He's on the app Cameo, and we bought a Cameo from him. I just want to see if he does it and tells people to stream my song, and maybe then he'll be like, "Oh, what is this?" We're trying!

The video is super fun. It has a lot of 2000s pop culture references: the Disney Channel wand drawing, a Lizzie McGuire-esque cartoon, the Britney Spears and Justin Timberlake denim outfits and—

And Britney's breakdown when she shaved her head and had the green umbrella and the little outfit. I [wear] the same outfit that she had, with the green umbrella. That was 2008, the same year that the Akon song came out. I literally went crazy with the references. I even did Regina George's mom in Mean Girls, which is a little bit later, but I still thought that was funny. It was definitely something that was important in my childhood, that movie.

You've been releasing these "micromixtapes" since 2019. Is "Now" set to appear on an upcoming project?

Yeah, I think I'm probably gonna put out an album in the beginning of next year. No promises because I'm not sure yet, but that's kind of what we're aiming for.

Your debut song "i hate u, i love u" with gnash was a huge hit, and it landed you your record deal with Island back in 2016, so what comes to mind when you look back on that track and its success?

To me it was kind of a happy accident. When I wrote that song I didn't think anyone was ever gonna hear it. I wrote it in my room by myself, when I was like 15, about a boy that I liked in high school. I didn't think I would ever do it for a living by any means. I think if that song hadn't had the success that it had, I wouldn't have taken the leap and gone and pursued this career at all, 'cause I never thought that it was possible.

I never thought that people would care enough to listen to my music, so I'm really grateful for that song. It kind of gave me everything I have. It was my first song I ever put out.

I'm sure it can be really daunting to have such a huge hit out of the gate, but you've really kept the momentum going with four EPs and an album, and you've garnered over 1.5 billion streams—and you're only 20 years old. Did you ever expect the career path that you've experienced so far?

No, not at all. It's weird because I had a Top 10 song, and I had never been in the studio with someone and written a song. I didn't know the music industry at all. I knew literally nothing, and I was like, "Oh, I have to become an artist now."

It was literally like I shot up, but I was still at the bottom, so I had to slowly build myself and figure out like, who am I as an artist? What is my message? What is my sound? It was a lot, but I feel like I'm finally at a place where I know who I am as an artist, and it took me a while to really figure that out, 'cause I was kind of thrown into the spotlight before I knew any of that.

Yeah, definitely. It's kind of amazing though, you got this launching pad. 

I'm so so grateful and so happy it happened the way that it did. I used to be a little bit salty that it wasn't technically my song, and I was just featured on it even though I wrote and composed it and everything, but now I look back and I'm grateful that it wasn't credited as my song, because I feel like it would have been hard for me to live up to that afterwards.

It was a great launching pad, but it didn't define me. I don't know how to put it. I feel like because my sound has changed so much, I didn't have to continue to do that. It kind of enabled me to be able to do whatever I wanted.

Your 21st birthday is coming up in November...

I get to have my first sip of alcohol. Woo, let’s go!

I think there might be a bar behind you!

[Covers it with her hand and laughs] Maybe I shouldn’t be doing this [here] ... my roommates are 23 and 21! It's not mine!

Do you have any plans to celebrate your birthday?

I had ideas before the world came crashing and burning down in front of my eyes. I'm from Napa, like wine country, and I've never gone wine tasting, 'cause I can't. I think it'd be fun to take [my Los Angeles friends] to my hometown and go, but now I feel like it'd be weird to go wine tasting with COVID and everything. Is that even safe? I don't know.

I'm probably going to do nothing, honestly. Every year on my birthday I have a full, actual mental breakdown. I will cry, and I always think that if I get drunk then everything will be fine, and I'll be happy. Oh my God, that sounds messed up. I don't mean it like that. I'm always like, "I should have fun and have a couple of drinks, and I'll be able to party." I turn into a demon. All of my friends can tell you. They're like, "I never want to spend another birthday with you ever again 'cause you go insane." I'll be dancing, and then the next moment I'll be bawling, and my friends will try to help me, and I'm like, "No!" And I yell at them. It's really scary. I honestly might just sit and reflect this year for my birthday.