Chicago has been called a lot of things, but “toxic ex” might be the most accurate one yet. On his new single “CHIANNE,” out now, Chicago recording artist Woes turns the city into a full-blown personification, casting his hometown as the kind of lover who keeps you up at night for all the wrong reasons.

Produced by Hobbes, “CHIANNE” is Woes locked firmly in his pocket — raw, unfiltered, and swinging over a hard-hitting backdrop that leaves plenty of room for the storytelling to breathe. The concept is as blunt as it is brilliant. “If Chicago was a woman, her name would be Chianne, and she’d be trying to kill me,” Woes explains. From there, the song walks the tightrope between devotion and heartbreak, loyalty and survival, using a wrecked romance as the mirror for life in a city that keeps shaping him whether he likes it or not.

The accompanying visual reel doubles down on the metaphor, planting Woes in front of some of Chicago’s most iconic landmarks — the Chicago Theatre, Buckingham Fountain, and Willis Tower — and letting the skyline do half the emotional heavy lifting. Admiration and frustration share the frame, which is exactly the point.

Stream “CHIANNE” on Spotify here: https://open.spotify.com/search/Woes%20CHIANNE

“CHIANNE” lands during a genuine breakout run for Woes. Earlier this year he was tapped as an official showcasing artist at SXSW, where he ran multiple sets across Austin and debuted “The Woes Phone” — a rehabilitated Chicago pay phone converted into a working microphone. That’s on top of a growing catalog of guerrilla-style performances that have included rapping atop moving, graffiti-covered box trucks outside Lollapalooza and Riot Fest. Unpredictability, at this point, is a feature not a bug.

His most recent full-length, Pressing My Luck, released via Pass The Butter, laid the groundwork for this moment. Tracks like “Swimming In Circles” and “Dancing Questions” showcased his jazz-tinged instrumentation and signature vocal delivery, while The Source praised the project for exploring “gritty sounds and tongue-in-cheek lyrics that define Woes’ approach to music.” Collaborations with Bless 1 (“American Cheese”) and John Wells (“Back to Back”), along with the pointed visual for “HIDE,” have cemented him as one of Chicago’s most distinctive emerging voices — a rapper pulling equally from Rage Against The Machine, Beastie Boys, Aretha Franklin, and Destiny’s Child, and somehow making it all cohere.

“CHIANNE” is the kind of record that only works if the artist actually means it. Woes clearly does. Press play, brace yourself, and let Chicago break your heart one more time.