Chicago native Alexander 23 performed in a daytime set on Lollapalooza’s opening day Thursday. He recently released a single, “Sad,” last month and dropped a new single, “Another Summer Night Without You,” on Friday, which will be featured in the upcoming third season of the Netflix show “13 Reasons Why.” He performed to a sizable crowd in his first Lollapalooza appearance. The Daily caught up with Alexander after his performance to talk about his Lollapalooza set and his music.

This interview has been edited for brevity and clarity.

The Daily: How was the experience of performing at Lollapalooza? Being that you’re from Chicago, what was that like?

Alexander 23: It was truly insane. It was surreal. It’s been a dream of mine, literally, since I can remember. And to look out and see such a cool mix of people I don’t know, and people I know from home… absolutely surreal.

The Daily: You dropped your last single, “Sad,” last month. Can you talk a little more about that, and the message you were trying to get across?

Alexander 23: “Sad” is a super important song to me. It hits really close to home. And it’s about how it can be so incredibly challenging and difficult to love someone so much, who’s going through a really hard time. The line between helping and hurting can feel so insanely thin. And that’s kind of it, it’s just trying to help someone as much as you can when they’re hurting the most.

The Daily: During your performances, you use your multi-instrumental talent in a lot of ways. What motivated you to learn to play multiple instruments and incorporate them into your performances?

Alexander 23: I kind of just got a bug after I started learning guitar. I was just like, “Okay, this is awesome. I want to do everything else.” And a big part of that was I always wanted to produce and record my own music. So if I learned everything, then I won’t have to deal with anyone else. I don’t want to rely on anyone else. It gives me just full autonomy over the creative process, which I really enjoy having.

The Daily: Can you speak to your Chicago upbringing and how that’s influenced your music?

Alexander 23: Chicago is such an amazing place to grow up because everyone tours through Chicago. So growing up, if I loved a band and I could convince my parents to give me enough money for a ticket, I was at the show every time. It’s very formative to, from such a young age, be able to see people who inspire you so much. And also, from around my area, there were artists that came up when I was like a little kid that made it feel super real. And they made it feel like it was possible. Fall Out Boy is from the town next to me. And they were blowing up when I was in middle school and high school. And for the first time I was like, “Oh, music could be my life, not just a hobby.”

The Daily: Where do you draw your main inspiration from when it comes to music?

Alexander 23: I draw inspiration from everything honestly, things that aren’t just strictly musical stuff. Animators that I found on Instagram, or friends that starting their own companies. For me, that is incredibly inspiring. Creatively, musically, what I draw from — it’s honestly a huge mishmash. My favorite artist right now is Bad Bunny, and my music sounds nothing like Bad Bunny. But if I take one element of a Bad Bunny song and put in my stuff, it’ll make it just that much cooler and better, at least to me. Melodically, I love old stuff like Hall & Oates, Fleetwood Mac, Tears for Fears, those types of bands.

The Daily: You’re dropping a new single, “Another Summer Night Without You,” tonight. Can you give a sneak peek into what that song is going to be like?

Alexander 23: This song is a super important one. It’s going to be on a TV show, which I’m super excited about. But the song means a lot to me. And it came together with that show in such a cool, organic way, and it intertwines perfectly. It’s just about really, genuinely missing someone, and how hard that can be just to live your daily life without someone we really miss.

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