Underground Rapper Woes Lights Up Lollapalooza With Guerrilla Set Under Train Tracks

Festival-goers at Lollapalooza 2025 caught an unexpected and electrifying performance by an underground rapper known as Woes, who took to the streets—and specifically, a spot under a train near the festival grounds—to deliver a raw, high-energy set.

The impromptu gig surfaced on Reddit, where a fan shared a video of Woes rapping passionately with a dynamic video projection behind him. His vibe was distinctly DIY and street-level, reminiscent of early 2000s underground hip-hop and nu-metal fusion. A projected message summed up the anti-establishment spirit perfectly: “Lollapalooza didn’t invite him but he’s here anyway.”

The community quickly identified the artist as Woes, confirming his presence on platforms like Spotify and YouTube, and many praised his authenticity and stage presence. There’s buzz about Woes potentially following in the footsteps of acts like Silly Goose, who moved from guerilla-style performances into official festival lineups. While Woes is not on the official Lollapalooza 2025 roster, his guerrilla set left a lasting impression on those lucky enough to witness it.

Fans and observers are keeping a close eye on Woes’ trajectory; his raw, outsider ethos combined with undeniable energy makes him one to watch. Social media followers can find him on Instagram and streaming platforms, catching up on tracks that showcase his unique blend of rap and rock influences.

This kind of off-the-grid performance adds a new layer to the festival experience—proof that the spirit of music and rebellion thrives just beyond the official stages.

Source: r/lollapalooza
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