Jefferson Airplane

It was the winter of 1968 when Jefferson Airplane took to the rooftop of the Schuyler Hotel in Manhattan. The band had just released their fourth album and had also just made the cover of LIFE magazine. High on life—and likely some other stuff—they blasted from their PA atop the nine-story hotel Midtown hotel: "Hello New York! New York, wake up you fuckers! Free music! Nice songs! Free love!" The band got a solid crowd going and at least one song in, but it didn't take very long for the NYPD to show up—the concert was causing traffic jams on the surrounding streets as New Yorkers crowded around the hotel to get a better look. Although the concert was quickly broken up, it was also captured on video by none other than Jean Luc Godard and D.A. Pennebaker. (Fun side fact: Many claim that the Beatles ripped off the band's performance with their show atop a London building about two months later.)
Watch the video here