Chicago-born rapper Taylor Bennett worked hard to step out of the shadow of his older brother, Chance the Rapper. Growing up in the same household enabled the two brothers to practice their craft together; as a result, their styles and approaches remain fairly similar, with the exception of Taylor’s tendency to rap at a much quicker pace during his verses. Taylor emerged as an artist in his own right upon the release of his debut mixtape, 2013’s The Taylor Bennett Show, which was recorded while he was still attending high school. Although he was adamant about prioritizing his studies over his music, a number of tracks were leaked in 2014; instead of chalking it up as a loss, Taylor chose to release the tracks officially as a mixtape titled Freshman Year: First Semester. As his high school years drew to a close, Taylor found the time to release his second mixtape, 2014’s Mainstream Music, around the same time that he started to play live shows — including two sold-out events at Reggies, a famous venue in Chicago. In 2015 Taylor released his debut studio album, Broad Shoulders, which, notably, was 100-percent sample-free; the album also marked the first official collaboration between Taylor and Chance, with a number of guest artists including King Louie, Donnie Trumpet, and Joey Purp. Taylor’s third mixtape, Restoration of an American Idol, arrived in 2017. Later that year, Bennett compiled a set of previously unreleased and unmixed tracks and released them under the title Throw Aways: Unmixed. The bouncy single “Minimum Wage” appeared in early 2018 followed a few months later by the EP Be Yourself. Anchored by the single “Streaming Services,” Bennett’s next project was the 2019 EP The American Reject, an eight-song set that featured contributions from Chance the Rapper and Ty Dolla $ign, among others. – Biography by Liam Martin

Adam Kelly, better known by his stage name Adamn Killa, is an American rapper from Chicago, Illinois. Adamn initially started making music at the age of 14, joining the group 197 O$G with fellow Chicago-rapper LUCKI.

Adamn would start to build a real name for himself throughout 2016 when he started working with Swedish rappers Yung Lean, Bladee and Thaiboy Digital, creating popular songs like “Psycho,” “Ten” and “Cashin.” He would later drop out from college to join them throughout Europe for the Warlord Tour, leaving his baseball career behind and pursuing music full time from there on.

He would briefly step away from music in 2021 as it was no longer a reliable source of income. He focused his efforts into other ventures, such as investing into various crypto currencies and doing Uber/Uber Eats. He eventually returned to music as he wasn’t as happy while not creating.

Adamn started to see a resurgence in popularity throughout 2024 with songs like “Prada at 13,” “Torta Pounder” and “A.D.H.D Rant 1.” He would capitalize off this buzz by releasing his February 2025 mixtape A.D.H.D Rant Vol. 1.

On June 20, 2025, Adamn released his highly anticipated mixtape, Generation Run.