Acid rap chance the rapper zip Continue Get all the best moments in pop culture and entertainment delivered to your inbox. Yesterday I left my wallet at home, says Chancelor Bennett, known as Chance the Rapper. It's 9 p.m. on an autumn evening at a Chicago recording studio, and he and his bandmates are packing for the night. Four days later, they put on their biggest show of the year, at the City Of United Center.Bennett sits next to me in high-waisted track pants and a fitted tee. He admits he feels a little overwhelmed having a new baby at home and a new tour to prepare for, and yesterday was proof. He took his 4-year-old daughter, Kensli, to Dunkin' for a rare treatment before school. It was the first day all week that he was able to make a morning drop-off and he wanted to feel special. She chose a shiny, sprinkled chocolate doughnut, and he realized that his pocket was empty. It's just crazy disappointment for a child, he says, shaking his head, clearly still unable to forgive himself. Luckily, another customer was more than happy to pick up the tab in exchange for a photo with Chance the Rapper.The whole 2019 span, in fact, was pretty frantic for the 26-year-old, who made the unthinkable choice a few years ago to avoid recording deals and give away his music for free. It has received more than 1.5 billion streams on SoundCloud since 2012, and it has earned millions of dollars in revenue, through live shows, merchandise and endorsements instead. Last winter, he directed six episodes of Rhythm and Flow, a Netflix talent contest he hosts with Cardi B, T.I., and a host of royalty RBC, which debuted in October. In March, he celebrated his wedding to longtime girlfriend Kirsten Corley, a pediatric behavioral therapist and Kensley's mother. In July, he released The Big Day, his first official full album (he had previously released three mixtapes, the last of which snatched three Grammys), which became a Billboard No 2 hit. He made his feature film debut in July with a cameo in the Disney remake of The Lion King. In October, he hosted Saturday Night Live for the second time, also performing as a musical guest. During all this, he also helped run SocialWorks, a nonprofit he founded in 2016 that works to improve the lives of young people in Chicago through art education, mental health services, warm clothing drives, and more. Bennett donated $2 million of his own to SocialWorks, including $1 million to Chicago Public Schools and $1 million to Chicago Mental Health Initiatives. In late August, Corley gave birth to the couple's second daughter, Marley. It was this development that caused Bennett to already packed the schedule to melt down- he felt he might not be the new father and go on tour at the same time. Eleven days after Marley, he announced, via Instagram (and a photo of himself his girls) that he would put off his highly anticipated, 31-stop North American tour until January. Yet he kept his promise in Chicago. On September 28, he performed one show for tens of thousands of people, which was attended by his brother Taylor and Chicago native Kanye West. The decibel level at the United Center, home to the Chicago Bulls, has reached levels that rivaled the Michael Jordan era. Chicago was just another loved one, whom Bennett couldn't disappoint. As he himself says on his 2018 track I Might Need Security: I sign my city as Bat-Signal. Chicago is a city divided by a river that cuts it horizontally. Head north, past the old money of Lincoln Park (where public schools are highly rated); past Cubs fans at Wrigley Field (which charges some of the highest ticket prices of any MLB stadium); past Edison Park (statistically one of the safest areas of the city, where a disproportionate number of law enforcement officers hole up at night); by the liberal enclave of Evanston (home of Northwestern University); and you will reach the rich, 90% white suburbs. Head south, past the Loop business district, and you'll begin to understand the place from which Bennett draws inspiration, both musically and civilly: selective enrollment of Jones College Prep (where Bennett attended high school); Harold Washington Library (where he recorded parts of his first mixtape); The White Sox's Guaranteed Rate Field (which charges one of the lowest ticket prices in MLB, and where Bennett started SocialWorks, promoting his third mixtape, Coloring, in 2016). Keep going and you'll reach Hyde Park (a predominantly black intellectual stomping ground for the Obamas, and by the way, where Bennett, at age 9, first heard Kanye West's track on the radio, which inspired him to buy College Of Education, the first rap album he's ever listened to) and eventually the heart of the South Side, an area most Americans know only as a caricature of gun violence. Photo: Mamadi Dumbouy; Stylist: DJ Smedley; Groomer: Tia Danzler with Dior Homme; Hairdresser: @Youssefbarber This part of Chicago is home to a middle-class neighborhood called Chatham, where Bennett was born. He is one of the fourth generation of Bennetts who lived on the same block, and his music, friends, family and Christian faith remain rooted here. It is for this reason that he runs his business different from perhaps any major artist working today. Bennett doesn't have a Hollywood agent or manager on the retainer. There's no slick branding agency or advertising firm out there purchasing megadeals. His music and social good operations are purposefully intertwined, organically, that avoids the org board. We really are a mom-and-pop-type shop. We're just working on a large scale, says Colleen Mares, his day in and day manager who ordered one one Bennett's early show, in 2013.One team member happens to be actual pop Bennett Ken Bennett is a veteran of the Chicago political world who served two mayors and helped orchestrate Barack Obama's unsuccessful 2000 congressional race, along with his history-making 2008 presidential run. Ken is currently a member of the SocialWorks board and treats his son's career as a political candidate. He found Bennett his principal career manager, Pat Corcoran, who worked with some South Side rappers, in 2013.Most of the roughly 10 people who work for Bennett's mini-label are native Chicagoans who have been with him since about then, including his lighting designer, a live video producer, and an artist who does branding and merchandising for the label and SocialWorks. Bennett's closest childhood friend, Justin Cunningham, is currently the executive director of SocialWorks. Reese White, a friend from high school, sits on the board of SocialWorks and helps with marketing. Essence Smith, whom Bennett and Cunningham met during their first year of high school, is SocialWorks' director of operations and communications. These are people I trust very much, Bennett said. It's not like our colleagues. It's more like ... just a simple conversation. Bennett and I climb into the back of a comically large SUV and he slides his Nintendo switch aside for me to take a seat. As we make our way south from the studio to its new downtown condo, we're talking about Cunningham, who was instrumental in keeping Bennett on the task as long as the two knew each other. From elementary school, he was the only kid who gave me a pencil because I came to school every day without a pencil. I would come to school every day without lunch, Bennett says. I just wasn't very organized it's the best way to say it, even to this day. Bennett did so badly in the first 10 weeks of high school that he was almost kicked out. By the end of the first quarter, he had failed six of seven courses. To stay, he took a strict schedule, dropping out of electives, stacking two biology classes on the same day, and enrolling in summer school. However, Bennett says he secretly paid Cunningham to do his summer school work. When Bennett was a junior, his father worked for a year in Washington, D.C., working for the Department of Labor under President Obama. Bennett, Taylor and his mother Lisa (formerly a liaison in public relations with the Illinois attorney general) stayed in Chicago. By the time Ken returned, Bennett was out of discipline. Having so much time without a strict dad, just, like, hanging out, and everybody starts buying guns, getting into drugs, having sex, growing up and making decisions... I ran it. Cunningham and Smith went to college. that won't be of high school with the rest of his class, not made. It was a strange space for me, says Bennett, recalling how he felt to let his friends move on until he stagnated, dreaming of a career in rap that felt far from achievable. So when I didn't go to school or get a job, it's obvious that my dad kicked me out, says Bennett, who spent the following year couch surfing in friends' places. A few days before The Bennett United Center's concert, Ken Bennett sits in a nearly empty stadium on the suburban Campus deKalb of Northern Illinois University. Bennett and his band created a scene imitating the United Center, complete with 30-foot screens and strobes, and bass flooding my body as they perform and customize the songs until they get them right.