Charles is joined by longtime friend and concert enthusiast Andy to recap their 24/7 Live Music Challenge — an ambitious attempt to see 24 live music events in just seven days, inspired by “Concert Joe” Sarkis of New York, who famously attended 1,000 shows in a single year back in 1992. Based in the Chicago area, Charles and Andy plotted their week using ChatGPT to build efficient nightly itineraries, hitting 24 shows across 16 different clubs without ever buying tickets in advance. They quickly learned that averaging three and a half shows per night was brutal — three shows in one night put them behind schedule, while four was a struggle to pull off even once, let alone repeatedly.

The conversation walks through each night in detail, from a jazz set at the historic Green Mill and a punk show at Subterranean to blues legends at Buddy Guy’s Legends and Blue Chicago, a folk night at The Hideout, and a storytelling-meets-live-band show at Martyrs that reminded them both of NPR. Along the way they battled real tornado warnings that knocked out power at multiple venues, forcing last-minute audibles, and stumbled into unexpected magic — snagging the last two seats at nearly every stop, watching Buddy Guy hang out in his own club ahead of his 90th birthday, and catching an incredible impromptu bass solo from a musician neither of them had heard of before.

By the end of the week, Charles and Andy had hit their goal of 24 shows for a total of just $313 in cover charges (well under the $1,000 budget Andy had braced his wife for), capped off by seeing Santana and the Doobie Brothers at a Tinley Park band shell. Standout moments included the high-energy punk band Squint and Kansas City act Season to Risk at The Liar’s Club, while the sheer physical toll — late trains, torrential rain, and blown-out eardrums — made clear why neither of them plans to repeat the full challenge. Still, both agreed it was a rewarding way to break out of their musical comfort zones, discover new venues worth revisiting, and appreciate just how much dedication (and money) serious “concert chasers” like Concert Joe put into their passion.

BANDS: Able Baker, Amyl and the Sniffers, Cherry Decay, Dog Caller, Dot, Grateful Dub, Greasy Gravy, Groove Witness, Jerry’s Middle Finger, Public Opinion, Santana, Season to Risk, Squint, Tunnel, liverwhip, the Doobie Brothers, La Croix Mystique, Majesty.

VENUES:  Andy’s Jazz Club, Beat Kitchen, Blue Chicago, Buddy Guy’s Legends, Cobra Lounge, Fitzgeralds, Garcia’s, Jazz Showcase, Martyrs, Salt Shed, Shubas, Subterranean, The Empty Bottle, The Green Mill, The Hideout, The Hungry Brain, The Liar’s Club, Tinley Park (band shell).

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