Photo Diary: All In A Day’s Work With Taylor Bennett

When Lollapalooza rolled around this year, more than 170 artists and bands converged in Chicago’s Grant Park to deliver one of America’s biggest weekends in music. However, some of the Windy City’s homegrown acts were busy on their own personal work circuits during the four-day span. Taylor Bennett, the rapper hailing from the city’s Chatham neighborhood, was one of them.

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On the day that his brother, Chance the Rapper, spent preparing for his headlining set on Lolla’s largest stage that night, Taylor was putting on for his city at Rolling Stone: Live Chicago, the magazine’s seventh annual Lollapalooza day party. The event was held at Studio Paris—the same venue Taylor used to ring in his 21st birthday earlier this year—and also featured Bishop Briggs and Run The Jewels on the performance lineup.

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Camera in hand, VIBE got to be a fly on the wall as Taylor manned the stage, handled his business, and showed up-and-coming musicians just how it’s done.