Chicago-born Taylor Bennett is not just the younger brother of Grammy winning Chance the Rapper, but he’s carving his own path as an independent music artist, entrepreneur and advocate. His career began in high school when he released his debut mixtape, The Taylor Bennett Show. While still prioritizing his studies over music, Bennett was next able to release his debut studio album in 2015 and sophomore album in 2017 which included a 13-minute short film. Taylor’s latest EP ‘The American Reject’ is a completion to his trilogy. In 2019, Taylor performed at diverse festivals and late night shows including Governor’s Ball, Hangout, Outside Lands, Life is Beautiful, The Tonight Show, Jimmy Kimmel Live, The Late Show and many more. Notably he headlined Chicago’s Complexcon.

Taylor started his own record label, Tay Bennett Entertainment which boast singer Bianca Shaw and ZXXK.

Taylor Bennett is a major advocate for the LGBTQ community and homeless youth amongst other initiatives. A statement he made: I think there’s a lot of people — in the music community, especially in hip-hop — that don’t feel okay with being themselves, that feel like being different is to be wrong. I’ve never shared that belief. My parents, my brother, friends and anybody that I’ve ever surrounded myself with, we’ve always accepted and respected each other for who we are. That’s something that I want my music to reflect as well. (The Fader, 2017)

If you don’t know Supa Bwe, you know his sound. The 29-year-old Chicago rapper has championed a combustible blend of hip hop, pop-punk, and R&B and helped carve out what would become a fertile, crowded lane occupied by younger stars like Lil Uzi Vert, XXXTENTACION, Trippie Redd, and YNW Melly. And yet, Supa is still constantly producing personal stylistic flourishes that no other artist could possibly replicate. On “Rememory,” from his new EP Just Say Thank You, he enlists Chance the Rapper to craft a dewy, electric piano-driven lullaby in which Bwe bounds in from left field and snatches the mic, instantly turning the track on its side with his singular singing voice—the sweet, sticky, Auto-tuned caterwaul of a lovesick feral cat.

Age is a foreign concept to Trapo. The 17-year-old creates trans-genre experiments that boom with a confounding sense of maturity, nuance and intimacy, but to the kid that has been recording and mixing his own music since he was in fifth grade, this sudden ascension isn’t surprising. “I didn’t play magic cards or anything like that. I wasn’t all that into sports. I’ve been only interested in music for literally my entire life,” the Madison, Wis. native says. “I believe in certain signs. There’s just no way that I could be doing this so young without having some talent that was just meant to come out.” Trapo was included on Pigeons and Planes’ “20 Under 20” and “Best New Artists” lists, and his arresting blend of dour hip-hop and hypnotic neo soul has been featured in outlets like BBC Radio, Complex, HipHopDX, The FADER and Hot New Hip-Hop. He was raised on gospel music and contemporary R&B, but his favorite artist is Isaiah Rashad and he extracts influence from every corner of the Internet. Motifs of DUIs, desolate nights with Remy bottles, steamy visages of Hispanic women and generational anxieties over social media appear throughout his discography, but each song contains an element of unpredictability that has made Trapo’s fan base a vocal and fiercely loyal one. “The whole, ‘you could be an astronaut’ thing you hear as a kid never got to me. This is what I want to do. My music feels like freedom.”

Morocco Brown is a 20-year-old rapper from Chicago, Illinois. Brown was only 15 when he produced his first mixtape and 17 when he decided he wanted to dedicate his time to making music. Once he graduated high school, Brown signed with Tay Bennett Entertainment as Bennett’s first signee. While his fans describe his musical style as “revamped, old-school Hip-Hop,” Brown prioritizes lyricism and says that “melodies come after” deeming his musical style as “indescribable.” As an artist, Brown’s agenda aims to encourage listeners to “whole-heartedly” remain true to themselves. Brown stays motivated by continuing to progress and excel as an artist, knowing his music will one day reach millions. The young Chicago artist looks forward to releasing his first album this September tilted, Manic.

K-Mu is a band of young musicians, ages 17-20, each from different sides of Chicago. K-Mu was formed in the summer of 2015 by Eddie Burns (Drums), Tony Milano (Keyboard), Kopano Muhammad (Vocals), and Johnathan Miller (Bass). They first performed together at a house show on the city’s north side but made their debut at House of Blues in January 2016. They then went on to perform at venues such as Subterranean, 27 Live, and even selling out Martyrs’. K-Mu plays music ranging from neo-soul to hip hop and their influences include Erykah Badu, J-Dilla, and The Social Experiment. They recently dropped their first single on Soundcloud, “Red Wine” early April and look forward to dropping their EP, “The K-Mu Tape” in the coming months.