There’s something about anniversaries that can make a person feel especially reflective. Leading up to the 10th anniversary reissue of his debut album, Lights Out Paris—which is out on vinyl for the first time this week—I wondered if Sims might be in the mood to think back to his beginnings of working with Doomtree and unpack some of the progress he’s made as an artist (and a person) since that album came out. It turns out he was in just the right headspace for a deep-diving conversation about the past, present, and future of his career.

After chatting with David Campbell for this week’s Local Show, Sims and I sat down at Black Sheep Pizza and split a Farmer’s Market Salad as we chatted about his growth as a writer, his strategies for managing anxiety and depression, and his complicated relationship with his fans. Because of the length of our conversation, I’ve presented this interview in two parts. Read the first installment of my interview with Sims here.

Andrea Swensson: Do you feel like, as part of this school of Minneapolis hip-hop that’s been branded as sociopolitical or "conscious," that people expect you to have opinions about modern-day events?

Sims: Maybe. But those people are people who are specifically looking for that kind of music, so they’ll find it where they can find it. I feel like, at this point—and I don’t mean to say this in an ungrateful manner—but I feel no responsibility to any listeners that I have currently. Or have had previously. Because I feel it’s an even exchange. I made some art, and you liked it or didn’t like it, and you supported it or didn’t support it, and then the next thing came out and you made that decision again. And that happens each time we do something, every time we come out. So it’s not my responsibility to retain you, or retain your interest, or somehow appeal to your sensibility and your own set of ideas and ideals. It’s not my responsibility to appeal to that. My responsibility is just to make sh*t, and if you like it, that’s awesome. And if you don’t, that’s too bad for both of us, or one of us, or neither of us. I’m fine with that.

The one freedom that I do have with being moderately successful is that I don’t owe any songs to anyone. I don’t have to make a single. I don’t have to make The O.C. 2 theme song. I mean, think about the pressure Macklemore is facing now. What do you rap about now? You have millions of fans who you’re like the good guy, you know? You assumed the character of the social justice warrior in some ways.

Or the white savior.

Yeah. And in some ways you’re the next Eminem and in some ways you’re totally not. In some ways you’re hated, in some ways you’re loved. But what do you do now? What’s your next record? What’s your next single about? It’s big pressure for him. I think Kendrick did a really awesome job of handling that. Because he’s the next 2Pac, right? Everyone loves Kendrick in this way—and they should—but like, he’s the next 2Pac? That’s a huge title to bestow on somebody. That’s a huge thing. And he did it in a way that’s like, "I make no singles. I’m going to make this crazy record about blackness, and about my interpretation of blackness in America in 2015. What’s that like?" Cool approach. I’m sure that the label hated it to an extent, you know?

So anyway, I don’t feel a responsibility to make anything political. It’s just part of the stuff I think about. All I’ve ever really tried to do is be honest about what I’m thinking and feeling, and not try to put on too much for you. Doomtree has somehow worked itself into this weird angle where we’re the good guys, in some way, too. And it’s so weird. We became safe rap at some point, and it bothers the sh*t out of all of us. Maybe not all of us. But a few of us for sure have talked about it. We’re not the best people. Some of us are kinda sh*tty dudes. [laughs] I don’t know. I believe there are a lot of people who come to Doomtree shows who expect that we’re the kind of people that we’re not. Like, expect that we believe the same sh*t that they believe, and that we champion the same causes that they support. I don’t know how the f*** we became safe rap. We didn’t aim to be, that’s for sure. We didn’t want to be the bad guys, but at the same time I think we became safe rap because we talk about the stuff we talk about. Like we never talk about gun play and misogyny and violence against women, violence against other people and sh*t. Maybe that’s what it is. So by default you’re the safe rap. It’s a weird thing.

Well, Stef talks about throwing Molotov cocktails.

Yeah! Totally. Totally. "We f*** your sh*t up, cuz sh*t’s f***ed anyway." That’s like a nihilist anthem. "Get Down" is like the nihilism anthem. There’s a pretty amazing Radiolab about nihilism. It’s called "In the Dust of this Planet," and it talks about Jay Z’s Magna Carta... Holy Grail and whether or not he’s a nihilist, and how nihilism has a history of being the coolest political standpoint to take, because everyone likes it for some reason. Like, "Yeah he doesn’t give a f***!"

On giving no f***s.

Exactly. "On giving no f***s." That’s a great title for a podcast.

Or the Doomtree book, volume 2.

Well, at some point f***s were given. You know? When stakes become real. I think we bought in at some point to the idea that this is our job, and then I think we assumed a responsibility and we thought that there were stakes at certain points, you know, and made huge mistakes—I mean, totally recoverable, but made huge mistakes because of the idea that "I’ve gotta do this, I’ve gotta do that." Bought into the idea that, alright, maybe I am this f***ing good guy rapper. Maybe I am this safe thing. Maybe I have a responsibility to my fans.

I think we’re in this really interesting time in art and journalism and online culture where you have to build a personal brand, and I’m really interested in the way that that boosts and then interferes with what you’re trying to do.

It makes it so sh*tty. Like, the fact that everyone has access, too, also makes it sh*tty. [Art] should offend people sometimes and it should be edgy and you should be losing fans and you should be gaining new ones, and you should not worry about that. Sometimes you should be wrong. Sometimes you should be sh*tty. I think that makes a better character. Like, everyone hates Jack from Lost. He sucks. He sucks. I don’t know why I think that’s like a relevant touchstone. [laughs] But it’s not right. Every good character should have flaws that you like and don’t like. It’s weird: being an artist or a public personality, you have to build a personality in some way. And in some ways you have to put shields up, and in some ways you have to deflect and not give a f***. It’s strange.

I asked Dessa about that once, because I feel like her brand is so rock-solid...

She’s really smart at that. I’m not. I just don’t know how to do it. I feel like, for some people it comes naturally, and it feels honest. For me, it doesn’t. It feels disingenuous every time. I feel like I’m lying, bullsh*tting, whatever. Before we decided that Doomtree was what we were going to do, I was in talks with different record labels in the early and mid-2000s, and they’re like, "What’s your story? Write the bio. Tell me what it is." And I was like, "I don’t f***ing know." It just never felt right.

I liked what you had to say about Allan Kingdom on The Local Show this week. Are there other younger artists that you’ve been watching?

Yeah, I mean that squad [thestand4rd]. Those four, pretty amazing dudes. Bobby Raps and Psymun and Corbin and Allan, and that whole crew, and tiiiiiiiiiip. It’s funny, they’ve been hanging around for a long time. Bobby was a big Doomtree fan back in the day, coming to the shows and stuff. And some of those other Audio Perm kids, like Taylor Madrigal, who’s tiiiiiiiiiip. He was a big Doomtree supporter back in the day. Those dudes are cool. Who else locally? There’s a dude who I’m getting beats from, who I’m working with a lot more collaboratively, he just turned 21, his name is Icetep. He did "They Don’t Work for Us," the beat, on Field Notes. He’s doing beats on the new record, and he’s come on to do some more general production on the record. I really like his approach, and I like the way he thinks about music. He’s young, he’s got a fresh idea about stuff. He’s in a group called Killstreak.

What would you tell 2005 Sims if you saw him today?

Probably just don’t worry so much. You know? You’re doing good. You’re doing the right thing. You’re ok. Don’t worry so much about what’s going to happen, and just do stuff, and make stuff. Make more sh*t and worry less. I suppose I should tell 2015 Sims that, too.

Read part one of my interview with Sims here.