Chicago-based recording artist Woes has released his Audiotree live session today, delivering an electrifying performance that showcases his signature fusion of punk, rap, and indie influences.

Woes’ raw, unfiltered energy and genre-blending sound have made him a standout in Chicago’s underground scene. For Audiotree, he performs tracks from his 2024 project Pressing My Luck, including “GOD IS A WOMAN,” “KNEECAPS,” “HIDE,” “TUNNEL VISION,” “PIPES,” and “CHEAPER BY THE DOZEN.” Adding an edge to the performance, Woes is accompanied by his creative collaborators—some of Chicago’s most prominent street artists—who appear in disguise, reinforcing his renegade artistic spirit.

 

 

A master of guerrilla-style performances, Woes has built a reputation for unpredictable, high-energy live shows. Last week at SXSW 2025, he took the stage with a payphone—stripped directly from Chicago’s streets—as his microphone, backed by a live drummer. Over the course of the festival, he performed six showcases and even staged impromptu pop-ups outside industry mixers and events. His unconventional approach to live performance is nothing new—last summer, he was spotted rapping atop moving graffiti-covered trucks outside Lollapalooza and Riot Fest, declaring, “We weren’t invited, so we came anyway.”

Woes draws inspiration from a diverse array of artists, including Rage Against the Machine, Beastie Boys, Aretha Franklin, and Destiny’s Child, crafting a distinct and unpredictable musical style. Pressing My Luck embodies his gritty aesthetic, interwoven with tongue-in-cheek interludes and skits. Standout tracks like “Swimming in Circles” and “Dancing Questions” showcase his versatility, blending jazz-infused piano backdrops with his signature vocal delivery.

Prior to the album, Woes made waves with viral Instagram visuals, including “i90 Blues”—where he brought Chicago traffic to a standstill for an emotionally charged performance—and “Hazmat,” where he raps about a toxic relationship while donning a hazmat suit and gas mask. His latest collaborations include “American Cheese” with Chicago artist Bless 1 and “Back to Back” with Baltimore’s John Wells, further cementing his reputation as an artist unafraid to experiment and challenge conventions.

With Pressing My Luck and his latest Audiotree session, Woes continues to push artistic boundaries, redefining what it means to be an independent artist in today’s music landscape.