Prisoners of Rock and Roll -- The Many Lineups and Lives of Lollapalooza

In this episode of Prisoners of Rock and Roll, we’re stage-diving into the sweaty, dusty madness of Lollapalooza—a festival that started as a punk-rock farewell tour and turned into a genre-crushing, culture-shaping juggernaut with more lives than Keith Richards.

Lollapalooza launched in 1991 as a sendoff for Jane’s Addiction—but it hit the road just as grunge was blowing up and quickly turned into something way bigger. It wasn’t just a tour—it was a movement. A 20-city, 20,000-screaming-fans-a-night, punk rock circus on wheels.

By ‘92, Pearl Jam was leaping into mosh pits, Red Hot Chili Peppers were funking up the chaos, and Rage Against the Machine stood naked on stage in Philly, duct tape over their mouths in a silent protest against censorship. This wasn’t peace and love—it was rebellion with a PA system.

Sure, it stumbled—people accused it of selling out. Then it died in ‘98, flopped in ‘04—but like any great rock act, it made a comeback. And Chicago’s Grant Park became its home base. From tattoo tents to $400 VIP wristbands, Lollapalooza has been underground, mainstream, gritty, glossy—always evolving, always loud.

So throw on your ripped flannel or your festival wristband—we’re digging into the birth, the chaos, the reinventions, and the legacy of a festival that didn’t just play the game—it rewrote it.

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