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Taylor-Bennett-VIBE-Lolla-3-1502392496

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

August 10, 2017 - 3:15 pm by Stacy-Ann Ellis TWITTER

VIBE tagged along with rapper Taylor Bennett for a day as he made moves during Chicago's biggest music weekend. 

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.

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.

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.

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Just as much of a flagbearer for family as his older brother is, Taylor Bennett starts the busy day with lunch at Hooters with his younger cousins, DJ and management team.
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Bellies now full, the crew makes their way to Studio Paris for Rolling Stone's seventh Lollapalooza day party, Rolling Stone: Live Chicago.

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A couple hours before showtime, Bennett cools out in the artist lounge of Chicago's Studio Paris. Just the night before, he'd played his own Lollapalooza aftershow at Reggies. Before heading up, he requests to hear Baka's song "Live Up To My Name" to get his mind right.

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British singer Bishop Briggs, who was also on the day party lineup, stops by to say hello.

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Taylor waits in the wings as his cousins and crew look on. 

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During the wait, the venue sound staff fumbles with wonky microphones. 

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Bennett kicks off his set with Restoration of an American Idol fan favorite, "New York Nights," before delivering an acapella rendition of the album's intro, "The Kid's Alright."

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To the frustration of everyone in the room, the mics were back on the fritz, cutting in and out. As DJ Mike P packed up his gear, Taylor apologized to the crowd and said, "I won't do another song until they fix my mics," before abruptly exiting the stage and retreating downstairs to the lounge. 

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"I've never walked off a stage before," Taylor says in response to the embarrassing technical difficulties. Down in the lounge, he isn't angry so much as he is disappointed in how the show was panning out. And rightfully so; sandwiched by Bishop Briggs and Run the Jewels, he is the only Chicago artist on the bill in his hometown. 

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To ease the sting of disappointment, the crew was treated to rounds of Tequila Don Julio 1942. 

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Bennett chops it up with a member of Run The Jewels' team, who've now joined the rapper in the green room.
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Ready to continue his set, Bennett shares one last laugh before taking the stage. 
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Unfortunately, feedback from the microphones still persist after nearly a 30-minute break. Visibly disheartened, Taylor cuts the music, apologizes to the crowd once more and delivers one acapella number before exiting the stage for good. 

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Taylor's crew, now 11-deep after being joined by some friends, piles into the runner waiting for them outside. DJ Mike P says his goodbyes and heads off for the day.

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The rest of the friends and family retreat to their crash pad for rest, showers, recreational drinks and some rounds of NBA 2K17 before catching Chance the Rapper's larger than life headlining Lollapalooza set that night.

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Festival Fashion: The Street Styles Of Lollapalooza 2017

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