Sims leaves you with a lot to think about. It’s been almost 24 hours since I watched him throw his first Mainroom headlining show, but the concert keeps poking questions at me, nudging me with a sense of unfinished business. At first, I thought I was the one who still had to process. Then I wondered if it wasn’t Sims.

A venerable solo musician and veteran Doomtree member, Sims has been at his craft for years. His first LP, Lights Out Paris, came out in 2005, and the Veldt-minded Bad Time Zoo followed in 2011. Three years later, an EP called Field Notes saw him explore a less hurried, more reflective space.

In June 2015, Andrea Swensson interviewed Sims about mental health, his writing style, and the state of his career. He said he struggled with writing about his anxiety and depression, because no matter what you rap about, “You’ve still got to sound cool.” He said, “I’m trying to think of how to make a song that you can play in the car, and to be fully honest, that you could play on a commercial too if you wanted, and still make it heady and sharp and urgent.”

More Than Ever, which came out in November 2016, is the product of all that work. The bangers (“OneHundred,” “Icarus”) thump. But the gut-wrenchers (“Shaking In My Sheets,” “Spinning Away”) outweigh them in number and in significance — and yes, you can play the new songs in the car.

Last night proved you can also enjoy them live. Sims played music from all over his career ("Weight," "Triple 6's," "Brutal Dance"). But I connected best with two intense cuts from More Than Ever, colossal tracks “Voltaire” and “Spinning Away." Sims rapped the latter from his knees, submerged in red light.

During the heavier songs, it looked like the pain got to him. When art pays the bills, the professional feeds on the personal, which can and did make for a weird, poignant concert. In the middle of “Voltaire,” he held the microphone to the side and let out an anguished, “F***." I tasted alkali.

Of course, plenty of lighter moments buoyed the mood, including a surprise P.O.S feature (“Spill Me Up”), an appearance by openers Air Credits (“No Limit”), and a supersonic medley that left Sims red-faced (“Sims Jong Il”/“Gray Duck”/“Uh Huh”). “If you feel bad about your dancing, just look up here,” he joked in the middle of a sort of cha-cha freestyle.

But Sims has been to his own depths. “The more you learn, the less you understand about stuff,” he told Swensson. “Buckets” translates it into first person: “I thought so deep I caught the bends.”

At an in-studio last December, he told Sean McPherson he’s learning how to pull back — how to say, “I don’t care.” And although I don’t think he’ll ever write a “Get Down” (P.O.S's "nihilist anthem"), I would say More Than Ever has helped him expel and organize his thoughts. From the way my head was swirling last night (and the way it hasn't stopped), I'm thinking his process isn't over; he’ll stew with his hurt for a while.

In the meantime, Sims will play his heart out. His music will feel like a shove to your chest. His delivery will come at your feelings. With the new album and Mainroom release show, he offered us a checkpoint. If last night was any indication, his audience will stick by his side.

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Opening for Sims, Artists to Watch Nazeem & Spencer Joles played six songs, including “Intro” and some new music. I had the good fortune to stand in front of DeCarlo Jackson, whose bright, smooth trumpet playing reminded me of Nico Segal (FKA Donnie Trumpet)’s work with Chance The Rapper. When I got home, out of all the music I heard last night, it was the “Smoke Daht” refrain that wouldn’t leave my head.

Chicago group Air Credits, aka ShowYouSuck and Steve Reidell of the Hood Internet, made me a fan. They tout “rap music from the future,” playing time travelers who left a wasteland future for our present day. “We decided to hop in a time machine,” ShowYouSuck told the crowd, excited about how well the set was going. “For being our ancestors, you guys sure are energetic.”

Not only could Air Credits time travel, they shapeshifted; Show You Suck went from sounding like Eaddy from Ho99o9 (“Camaro”) to Daveed Diggs from clipping. (“Westside”) to Kanye on Yeezus, playing 14 different songs in 35 minutes. He held two microphones, one of which deepened his voice into a roar. On the production side, one moment, the beat sounded like vintage Jay Z (“All I Need Pt 2”); the next, it might have belonged to composer/dance producer Nicolas Jaar.

An impressive number of people already knew the lyrics, and I’m on my way, having already listened to their album Broadcasted twice. “So this is going well, right?” ShowYouSuck asked the crowd after standout track “Of Blood.” He knew they nailed it.

Milwaukee’s WebsterX was less successful in winning over the crowd, sticking to trap norms and hype tricks. Guests, such as Finding Novyon (“On My Way”) and Lex Allen (“Cream And Sugar”), piqued my interest, and it was fun to see ShowYouSuck jumping in the crowd (holding what looked like a ventriloquist’s dummy).

Cecilia Johnson is a staff writer for the Local Current blog. Emmet Kowler works with lights all day and takes photos after dark.