For Midwest native Alexander 23, it’s been a fast trip from bedroom-recording obscurity to performing at one of the country’s most prestigious music festivals.

Alexander 23 has only an EP’s-worth of music under his belt, but he’s nevertheless impressed industry big wigs enough to be invited to Perry Farrell’s Chi-Town festival stalwart. His latest offering is “Sad,” which will be accompanied by a video in the near future. He announced himself earlier this year with “Dirty AF1s,” a track whose seriousness, in typical Alexander 23 fashion, is belied by its video’s warped sense of humor. That odd interplay, between the solemn and the silly, has become something of his calling card. In addition to the upcoming appearance in Chicago (8/1), Alexander plans to fill out his summer opening for mxmtoon (8/19-10/31) and Omar Apollo (12/10-12/15).

Where are you from?

I’m from Chicago originally. I lived in New York for four years and moved to Los Angeles one year ago.

Cool. I just watched a video – I don’t know if it’s the official video – for “Sad.” It was just a single, stationary shot of a rainy New York street.

Yeah, I was in New York two weeks ago, and I shot that on my iPhone, over on Perry Street in the West Village.

Give me, if you could, an idea of how you got into music.

My dad played guitar a bit, and when I was eight, I tried it; I hated it, and quit. [laughs] But then I picked it up again later, and it became an obsession: when other kids were playing video games, I was playing guitar. I’ve since branched out to piano, bass, drums.

And this is in the Chicago area?

Yeah, exactly.

I get the impression that you have a DIY approach to your music-making. Is that so?

Yes, I do all the production myself. It’s just me alone in my house, trying stuff until it doesn’t suck anymore.

Who were you listening to as a budding musician?

When I first started playing guitar, it was John Mayer. That was the original influence. Then there was the Chili Peppers. And recently, there are a lot of artists around my age who are super inspiring.

As I listen to you sing, one characteristic is immediately apparent: big intervallic leaps. Where does that come from?

That’s a good question. My dad listened to a lot of progressive rock, stuff like Super Tramp. That stuff is full of melodic leaps. Also, I think that’s where I get my kind of non-traditional song structure from.

Congrats on gaining traction earlier this year!

Thank you! The first song came out in March, “Dirty AF1”. So it hasn’t been too long, actually. And then I went on tour with Alec Benjamin, which was an enormous launching pad, playing these songs that no one had heard.

How did Benjamin become aware of your music?

We just had a ton of mutual friends in LA.

What do you think of LA?

I love it, even if I miss New York. LA has given me the mental space to process what happened to me in New York.

Tell me a bit about “Mars.” The whole balloon love triangle motif in the video, in particular, is hilarious. Where did that come from?

A friend of mine growing up is a balloon artist, so I figured why not put that in? I’m always looking for ways to counterbalance the seriousness of the songs with something more lighthearted.

Yes, I noticed that especially in the video for “When I Die,” where three versions of you–young, present-day and old–get into a variety of misadventures. There’s a wistful tone to the video, but its also played for laughs. Correct me if I’m wrong, but you seem to have honed in on humor combined with pathos.

I appreciate you saying that – it’s super intentional.

So how did you get involved in Lollapalooza?

It’s always been a dream of mine, being from Chicago. Growing up, that was my barometer for “making it.” Now I understand that I have a ways to go. I’m just super grateful for the opportunity.

How many sets will you be doing?

Two, one at night and one during the day.

Any plans for an EP or LP after Lollapalooza?

Definitely. I’m not yet sure what form it’ll take, though. But I’m definitely building towards a project in the fall. In any case, expect a steady flow of music. The idea of ever stopping is terrifying.