Chance the Rapper and his younger brother Taylor grew up in Chicago
Chance the Rapper’s brother Taylor Bennett is charting his own path.
The younger brother of the Grammy award-winning rapper is an artist in his own right, with several mixtapes, sold-out shows and four albums under his belt.
"We definitely share a chemistry of music, and we both push each other to be better artists, for sure," Bennett remarked in an interview with the Chicago Tribune in 2016 on their shared rap prowess. "I don't know if it's in the DNA. It might be. I just like to think of it as a God-given gift. Sometimes I ask myself, why does this sound so good?"
He is also aware of the large shadow his brother has cast on the industry, and Bennett realizes that he will always be considered “the younger sibling” to his famous brother. But, as he told NBC 5 Chicago, he is content with his trajectory as an artist.
“I think that in terms of a musician, I think Chance is amazing. I’m still growing," he said. "I think that being yourself is a huge step toward who Taylor Bennett really is but I’m still finding myself. I still have a really large journey to go.”
So who is Chance the Rapper's brother? Here's everything to know about Taylor Bennett and their close relationship.
He is a rapper
Bennett followed in his brother’s footsteps and has carved out his own rap career. The younger of the Bennett brothers produced multiple mixtapes beginning in high school before releasing his first album, Broad Shoulders, in 2015.
"I've been interested in being a rapper since I was 9, but I started putting music up on SoundCloud and YouTube around the age of 14," he told the Chicago Tribune.
Bennett sold out his first show at Reggie's Rock Club at the age of 17, which was all the motivation he needed. "I saw the fans come out, and I thought, this is what I want to do. When you actually see the fans in person and see them singing the lyrics, it creates a whole different experience," he said.
However, Bennett knew that he would inevitably be compared to his older brother.
"It's a double-edged sword,” he said. “A lot of people find out about me because of who my brother is, but that's even more of a reason for me to uphold my own truth. ... If they like the product, they like the product. And if they don't, they don't."
He has three sons
In 2022, Bennett opened up to PEOPLE about the dynamic between his boys.
“They're both very determined, which reminds me of my brother and I,” he said. “So if they want something, they're going to figure out how to get it. A lot of times, they know now it's not just with crying, sometimes it's with accepting what we say and then literally sneaking into the other room, and I come back and I'm like, ‘Wait a minute, how did all of these Oreos get on the floor?’ "
His brother is his best friend
Chance refers to his brother as "the Donald to my Mickey," and sees many parallels between their sibling bond and the animated pair’s friendship.
"Donald and Mickey complement each other really well and I think Taylor and I are the same way. We push each other to be better musicians, fathers, brothers and partners but also always have each other’s back," the Grammy winner told PEOPLE in a 2020 interview.
"It’s a blessing to have the ability to say my brother is somebody who I agree with enough and admire enough to support each other through our lives and our careers. What he aspires to be, I aspire to be," he added.
Bennett echoed the sentiment in a birthday post to his older brother on Instagram in April 2023.
“Happy Birthday 2 My Brother! This Guy introduced Me to Music & opened my mind to being Independent & One Day Gave Me a Job That changed my Life Forever‼️ Proud Brother, Manager, Security, & Whatever I need to Be as long as your My Big Brother💙," he wrote.
He and his brother got into squabbles growing up
Like many siblings, Chance and Bennett got into some scrapes as kids.
"We definitely fought growing up," Chance told PEOPLE about his relationship with Bennett. "I think the older we got, the more it set in that no matter what we will always have each other and that family is a bond we won’t take for granted."
He came out as bisexual in 2017
In a series of posts on X (formerly known as Twitter) in 2017, Bennett revealed that he was bisexual.
Ahead of his 21st birthday, Bennett revealed that he wanted "to be more open" about himself in hopes of helping others struggling "with the same issues."
"Growing up I've always felt indifferent about my sexuality & being attracted 2 one sex & today I would like to openly come out to my fans," he wrote at the time. "I do recognize myself as a bisexual male & do & have always openly supported the gay community & will keep doing so in 2017. #ThankYou."
Five years later, in 2022, the Coming of Age rapper and vocal LGBTQ advocate reflected on the reception he received in the aftermath of his revelation.
“There was so much love, and I've never really felt like I was isolated," he said. "Also, sometimes I don't realize how strong the words that I might say can be — your words actually start to touch people and they start to move them and change the perception.”
He grew up in a disciplined household
The music business can be very challenging, but Bennett believes his disciplined upbringing has helped him and his brother successfully navigate the industry. His parents, dad Ken Williams-Bennett and mom Lisa Bennett, assigned their boys a few chores to instill a sense of responsibility.
In a conversation with PEOPLE, Bennett reminisced about routine tasks of sweeping the floors and cleaning bathrooms on weekends while handling the dishes and kitchen tables during the week.
“If you didn't do what you were supposed to do during the week, instead of $10, you got $5, which meant that you couldn't get the slice of pizza and drink when you get on the train after school. We were taught accountability at a very young age," he said.
His family is friendly with the Obamas
Williams-Bennett once worked as part of President Barack Obama’s administration, in the role of White House deputy assistant. Prior to that, he served as the state director for then-Senator Obama’s presidential campaign.
Bennett's mother also worked for the Illinois attorney general, and Williams-Bennett eventually moved on to a position as Deputy Chief of Staff and the Director of the Mayor’s Office of Public Engagement for former Chicago Mayor Rahm Emanuel.
Bennett and Malia Obama were once photographed hanging out at Lollapalooza together in the summer of 2016, and later that year, the young rapper told the Chicago Tribune, "They're great people, a great family. I was just in Washington, D.C., last week for the Christmas tree lighting. We got to see Barack and Sasha, Michelle was there."
He works closely with his brother and father
Chance the Rapper made his name on the independent circuit, becoming the first artist to win a Grammy Award for a project that was available only on streaming. When he started searching for management, Chance approached his younger brother for help.
"And I was like, 'Chance, I think that we need to ask my dad to come in and help do the senior advisory for the team,' " Bennett told PEOPLE.
He mentioned that in their family's business dealings, emotions never played a role. They were taught early on that “personal disagreements” should not hinder their responsibilities, and failing to complete tasks, like cleaning the floors, meant no allowance.
“So it's a thing where we were taught at a young age that if you want something then you have to do something for it and that we shouldn't let the emotions affect the business of where we're all trying to get to," he said.
He added, “I think my father, a lot of times, finds himself in the dad position where he's like, 'Well, you're both my sons and I love you and you're both right, but really this is right.' "
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