It’s the third stop on the Bucket List Tour, now in Vancouver, and Saba is backstage with his manager, contemplating the addition of an old SoundCloud loosie to the night’s setlist. A fan who had come to shows in both Seattle and Portland already was spotted in the audience, and he’d made it clear that “Temporary” was his favorite song.

“He came to three straight shows. We definitely gotta replace something,” said Saba.

Later, when Saba explained the song choice to the crowd and performed it (for the very first time, no less), the response was electrifying. Another fan, pressed up right against the stage for the duration of the show and draped in the iconic Chicago flag—an uncommon sight in Canada—rapped along to every lyric with drunk enthusiasm.

This kind of fandom is new to Saba, who is headlining his own tour for the first time. “On the Mick Jenkins tour and the Jazz Cartier tour, I met some fans, but this is the first time they’re my fans. Like, ‘we’re coming here just to see you,’” he told me.

As an independent artist, Saba financed the Bucket List Tour himself, and at only 22-years-old, he’s already accomplished more than most artists can dream. Unfortunately, his recent successes don’t equate to carefree living. Two weeks before the beginning of the tour, Saba’s cousin and fellow Pivot Gang artist John Walt was tragically killed. It’s a weight he’s been forced to carry on the road.

Luckily, he doesn’t have to carry it alone. His team is populated with his friends who are always nearby, though this evening they’re mostly hungover. (The audience would be thankful that Saba doesn’t drink if they could see the state of his entourage.) Being somewhat shy and reserved, Saba can be difficult to read at times, but onstage, he’s beaming, animated, and comfortable. Perhaps that’s why John Walt’s passing hasn’t slowed him down; his profession and his means of escape are one in the same.

As Sylvan LaCue (formerly known as QuESt) performed his opening set, the bouncing crowd tested the integrity of the building, and backstage—which was actually below the stage—I sat down with Saba for a conversation beneath the squeaking floorboards.

DJBooth: This is your first headlining tour ever. That must be wild.

Saba: It’s wild. I’m still figuring it out.

Your most recent single, “Monday to Monday,” is your most streamed song to date, which shows that you clearly haven’t come close to hitting a peak yet.

That shit is crazy. Hit a million plays [on Spotify] hella fast.

Biggest single so far, technically. Are you starting to feel the effects of your career taking off?

It’s funny—the first two shows we did meet and greets after the shows. It was like I was Kanye or some shit [mimics fans freaking out].

Is your burgeoning career taking away from your personal life?

The lifestyle is kinda really similar to the way it’s always been. I’m a pretty chill guy. Mostly I’m just at the crib playing video games. I do a lot more fun shit now, like go-karting, indoor skydiving, and shit.

So, you actually have more time for hobbies now.

Yeah, if anything I have more time to do more fun shit [laughs]. Some weeks I’ll be busy as fuck, but there’s always time to hang out with friends and see my girlfriend.

How long have you been together with your girlfriend?

Like four years. It is possible to be a touring artist with a girlfriend. Not nearly as challenging as people make it sound.

We all know from tabloids that fame makes it impossible to maintain a relationship.

That shit is all made up [laughs]. People do what they want to do. If you’re a huge artist and you’re doing a show every day and selling out stadiums, it’s very easy to also have your girlfriend there. If you can afford to rent out the stadium, I’m sure you can afford a $100 flight.

Correct me if I’m wrong, but of the Chicago music scene, it seems like you’re closest to Noname. Is that true?

Yes.

You guys talk like family about each other, and you mentioned on Hannibal Buress’s podcast that “Stoney” and Noname’s “Diddy Bop” are “cousin songs” because they were made at the same time. She’s said she sees Chance like a younger brother; you’re also younger than her, is it the same kind of relationship?

Yeah, I do view Noname as a big sister. She knows my grandparents and shit. She’s been recording in my basement since I was 16. So it’s family to me.

It seems especially common in Chicago to have musical collectives as opposed to singular artists. SaveMoney, Pivot Gang, Free Nation Rebels, etc. How does that come about?

Chicago has a gang mentality. Even if you’re not in a gang, a lot of times in Chicago you might operate as a gang. Even if we’re not out doing crime, there’s still a lot of gang mentality, even for the nicest kids. It’s actually just now getting to a point where, because of the music, everybody’s friendly. The Chicago before that was very “if you’re one thing, and we’re another thing, we hate each other.” But it’s cool ‘cause the music has helped to break down that barrier.

You’re from the West Side. How would you describe that in relation to the South Side or the rest of Chicago?

The West Side is very unsung. It’s just not celebrated. It’s like, a forgotten about part of the city.

Are you trying to bring more clout to the West Side, or would you rather break out of that gang mentality and help bring up the city as a whole?

It’s a little bit of both. Sometimes it feels like the people in Chicago don’t take the West Side seriously. A lot of times its dance music or bop music or drill shit and people just overlook [the West Side]. We haven’t had a guy “do it” in a long time. Lupe [Fiasco] was probably the last West Side rap star. So it’s cool being from there just to be a hope for people who have really lost hope. We always love our Chicago artists regardless of where they’re from in Chicago, but most are from the South Side. Sometimes it doesn’t feel like it’s possible to even happen in [your] neighborhood. So that’s why I always say the West Side and talk about it as much as I do because I want to be that inspiration.

West Side songs like “Westside Bound 3” have a lot of references I’ll probably never understand. But I guess in the same way that LA rappers shout out “Crenshaw” until we eventually know what it is, the same logic follows.

I could give you three references now just thinking of “Westside Bound 3.”

Hit me.

“Austin my grandmama house.” Austin is the neighborhood that I’m from, where my grandma lives.

“Madhouse on Madison.” That’s what they call the United Center, the Bulls stadium.

“My head to the sky like a Jesse White backflip.” Jesse White has a tumbling team in Chicago, so they do flips and shit.

I’m so glad I finally know that. I’m always singing along without knowing what the fuck I’m saying. Are you checking on Genius to make sure people are getting it right?

I need to update that shit. They got a lot of shit very wrong. When I had the time I used to [transcribe and annotate my lyrics on Genius]. I used to care so much. But it’s like, eh.

Fuck it, it’s art.

It’s art! [laughs] Do what thou wilt.

On Bucket List Project there are voice clips from fans, family and artists sharing their bucket lists. How’d you collect those?

I just sent a tweet out trying to get as many fans as possible to send me their bucket list. That was probably the hardest part of the tape, just picking which bucket lists to use.

My girlfriend was really proud that the women on the tape have higher ambitions than the men.

That was definitely a goal of mine. Just listening to the tape and thinking, “add more women.”

If you had to do your own voice clipping, what would be your bucket list?

It honestly switches every day. Sometimes I don’t think about what’s on my bucket list and I find myself crossing off some shit. Like, a headlining tour, for example. That’s been on my bucket list for my entire life. That’s one of the reasons we’ve been doing everything we’ve done—to get to this point.

I know you’ve said before you don’t have specific plans in terms of future music and merch, but in broader terms, are you planning to stay in music for your whole career?

I started as a producer so I’d like to get back into that role. Produce a full project—that’s something I’ve always wanted to do. Most of my aspirations, even outside of music, still involve art. I used to draw a lot. I wanted to be a cartoonist before I wanted to be [a rapper]. I tried to do it when I was a freshman. I was terrible. I was using Windows Movie Maker trying to animate shit. But it was never really anything I took seriously. If I had time to focus on something like that, I think that’s something I’d be good at. Everything’s just with time—the more I knock this [music] shit out, the more time I’ll have to do other shit.

What artists have you been listening to recently?

I listen to Sade. That’s my latest obsession. I listen to Sade and a lot of trap shit. That’s pretty much it.

So, to get a break from the Chicago sound, you move to the Atlanta sound?

I listen to way more trap music than shit that I would make. Like J. Cole and shit like that, I would never listen to [laughs].

You had so many Chicagoan features on Bucket List Project—Twista, Noname, Ravyn Lenae, the list goes on—and you’ve done a great job of repping your city. Now that your name is growing, is there anyone you’re dying to collaborate with?

Uh, all of the same people, honestly. They’re kinda my favorite artists. As far as features, I definitely believe in the organic route. All those people I have relationships with and love like family. That to me makes the best music. Unless I’m able to get fucking Sade. Or Bone Thugs-n-Harmony.

Do you try and keep the collabs in-studio?

Scheduling-wise it’s not possible sometimes. But you won’t have to worry about whether it’s weak or not if you have a relationship with them.

Plus it’s probably easier to constructively criticize.

You don’t want to reach out to somebody who’s not gonna take a second attempt at your song [laughs]. If they don’t get it right the first time, and you don’t feel comfortable enough to ask them “can you change this line,” you probably shouldn’t have done it.

Some artists get a pass through. You can’t ask Young Thug to re-record. He’d be like, “Nah.” Or Kanye.

Yeah, those are the exceptions.

So there’s no one you haven't met yet that you want to work with, besides Sade and Bone Thugs?

Pharrell. I’m not prepared yet, but I would like to do a song with Kendrick Lamar and out-rap him. I think that’d be a fun little experiment.

You think you could do it?

I could definitely do it. I’m not there yet. I gotta get to writing every day. Like, prison bars. Working out in the gym. I gotta live a little more life. I’d like to get out-rapped by André 3000 one day, maybe.

Have you ever been concerned about getting outshined by a feature on your own song?

That shit is encouraged, if anything. I think it’s usually a good thing when that happens. I think [Joseph Chilliams] out-rapped me on “Westside Bound 3.” Until it gets to that point where somebody, like, eats me. Then I might have a different answer. But it’s never been on some Jay Z and Eminem shit.

What about when you’re the feat—

Instantly try and body that shit. Don’t let them breathe at all.