It’s just after 8:30 p.m. when Jean Dawson strolls into the press tent at When We Were Young fest. He’s completely zipped up in an all-black bomber jacket. So zipped up, in fact, it conceals much of his face. Thick coils of hair fall into his eyes, but his smile when we shake hands is so pure and disarming, it’s easy to dismiss the cloak and dagger altogether.

Dawson might seem shy in person, but he’s anything but that in his music. The 27-year-old musical polymath and filmmaking creative is as adventurous as they come, producing an aggressive jukebox of styles ranging from alt-rap to experimental dream pop to punk and reverb-soaked shoegaze, all while bringing his eccentric visions to life through the music videos he’s directed.

“When I'm working on these things, the visual language that is my music sometimes supersedes the sound, which means everything I've ever wanted to make sounds like a coming of age film, regardless of genre,” Dawson says. “Whether it's rap, rock, R&B, whatever, as long as it's coming of age, I'll never have to stop coming of age till I die.”

Three solid albums in, Dawson’s been crowned a generational treasure, working with artists like Sza on 2023 single “No SZNs,” releasing his documentary, 2021’s Burnout, and selling out U.S. tours.

Ahead of his When We Were Young set on Saturday, the Weekly sat down with him to talk about finding a kindred spirit in Sza, playing nostalgic fests and why seeking help is so important.

Is it weird at all to be playing a nostalgic festival when you’re not necessarily nostalgic yet? I think rock music and alternative music have done a very good job of ushering in the next generation. It's very traditional for a legendary band to bring out somebody that they like. The festival putting me and some other guys in the lineup that are relatively young just shows that they're still looking out for the next generation.

You started listening to an array of musical styles during your long commutes crossing the border from Tijuana to go to school in San Diego. What was the first concert you went to that blew you away? Honestly, it was Mac DeMarco. My brother took me, and it was maybe 2015 in Los Angeles. That was the first concert I ever went to. I’ve played shows since I was 13, but I never went to shows. Couldn't afford it. But it blew my mind, and then he ultimately became a friend. He's inspired me a lot.

You have so many influences. When We Were Young is obviously based around pop-punk and emo. How did those genres have an impact on you as an artist? What I've always admired from the pop-rock period is that hooks are important. Choruses are very important. But I've never seen myself as a punk kid, or a hardcore kid, never called myself that because I knew kids that were actually that to the core. It's not beyond the scope of what I'm comfortable with doing in terms of performing, and I'm proud of that. But my biggest inspiration is probably Prince. Prince was undefined his entire life, and that's something I aspire to be — indescribable.

Do you remember the first time you heard Prince? It was played in my household a lot, but the first time I took it upon myself to listen to Prince, I was probably in middle school. I had gone through a breakup, and my friend was like, 'My dad plays this all the time. You need to listen to this.' And I was like, I'm him! I feel like exactly what he's talking about. I remember downloading all his music illegally, too. Sorry, love you.

I feel you are versatile enough to fit in with any artist. You’ve done songs with Earl Sweatshirt and even Sza. How was it working with her? I've never worked with somebody where I felt like I was looking at a mirror. Sza is ... she's like the songbird of our generation. She wears her emotions on her sleeve so much to where it'd be hard not to relate to her. You would have to try not to relate to Sza, which is stupid. When we were working, or just having a conversation, I haven't felt I've been a kindred spirit to somebody like that in a long time. And bless it be to her to reach out to me and want to do anything. Now we have a friendship that's beautiful. She's exactly who you think she is in her best way.

You also tackle a lot of personal things in your music like identity and fragile masculinity. Does being vulnerable about those topics come easily to you? I had to work to be translucent. I feel like people lie because we're afraid of things, and I didn't want to have any fears, except for God. I'll tell anybody, anything they want to know about me. As long as it's just about me. I do hide myself, like right now you can only see 4% of my face, because there's some things that I'm still working towards.

But when it comes to my emotions and the inner workings of who I am, it's much more important for me to share them, just for somebody to see that I'm also working through them. I guess the cliche is to not feel alone, but it's real. I've spent a lot of time alone. But I don't want to be left alone with just the mirror of my own thoughts. I use the world as a diary, instead of using it as a shield. Sometimes I need to say things to say them. Whether people are going to listen or not, my purpose isn't to be seen, I think my purpose is more so to be heard.

This is a lonely generation in a way, between the internet, the pandemic and with mental illness issues coming out of the woodwork. It’s nice to see you putting yourself out there as a mirror to other people. It's Depression Awareness Month right now, and when I started taking my depression medication for my anxiety and depression, I was 21 years old, and I was afraid to tell anybody. I thought, you guys are gonna think something's wrong with me. But the more I started to be like, actually, why don't I just tell everybody? Then I took the fear away from it. How people are going to perceive me is none of my business. How I'm going to perceive people is none of their business. But how we can perceive something as general as taking medication should be something positive.

If you get to that point where you don't want to exist anymore, it's very important to find every single outlet to try and get better. That's where I was. Now when kids or individuals come up to me and say, ‘Hey, you saved my life.’ I'm like, No, you saved your life.

I think that's why me and Sza really had a strong connection. Because she talks about her emotions and she's vulnerable with how she feels. It's a very hard thing to do, especially in the world we live in right now that uses comedy and jokes as a way of covering how we feel. But sometimes it's not all that funny. Sometimes it's like, Hey, I'm an actual human being.

Anything you’d like to leave us with before your set? We should all try to be a little nicer to each other. I think we'd live in a better world. That's pretty much it.