Taylor Bennett's father, Ken Williams-Bennett worked for the Mayor of Chicago and his mother Lisa Bennett formerly worked for the attorney general, who ensured that he would pursue his dreams while also making it through school. He attended Urban Prep High School. He and his brother demonstrated an interest in the arts very early on, rapping with each other and building their skills. In 2014, Bennett and Jake Kalmin, his manager at the time, were charged with assaulted battery for allegedly severely injuring a teenage Columbia College Chicago student at a party. They beat the victim badly after he stepped on Bennett's shoe.
Music career
Much like his brother, Bennett has developed a unique sound and style of rapping. Some artists that have influenced his growth as a musician include Twista, Nas and Kendrick Lamar, which has had a noticeable impact on his music. He also claims that Kanye West's College Dropout had a significant role in his ability to see the fun-loving side of music. Bennett's brother preferred that he build his own fanbase before he began working with and promoting him. Chance believed this was an important step in his development as an artist. Bennett finally started selling out shows at local venues such as Reggie's and even opened for his idol Nas at a Lollapaloozaafter party in 2014. Following his success, he and his brother released a track "Broad Shoulders", which is also the title track of one of his most recent mixtapes. In 2015, Bennett released mixtape "Broad Shoulders". It features artists such as Logan Parks, Talia Stewart and Jordan Bratton, most of whom are native Chicagoans. This was also his first full album without any elements sampled from preexisting songs. In July 2018, Bennett released a single titled "Rock n Roll" along with the video from his upcoming EP, "Be Yourself".
On October 17, 2014, an article was released from dnainfo reported that Bennett was involved in an altercation at a house party in his native city of Chicago that left his victim with major head trauma. The article states that Bennett and his friend attacked the victim after the victim stepped on Bennett's shoes. The incident was captured on video by attendees at the party, who would identify Bennett on social media. Bennett would turn himself in and be released on a $75,000 bond.
