While attending high school in Milwaukee, Wisconsin, Midwest rapper IshDARR launched his career as a student. Born Ishmael Ali, he absorbed his father's jazz and rap records during childhood, among them selections by Lil Wayne, A Tribe Called Quest, De La Soul, and the Pharcyde. As a freshman at Messmer High School, he aligned with his older brother's circle to deliver raps at house parties and talent shows. Once those associates graduated, he stood without partners. Football offered a viable alternative path, nearly prompting him to abandon music until his instructor—affectionately called G Flat by students—provided motivation. Displaying an affinity for memorable hooks in the vein of Lupe Fiasco and verbal agility akin to Vince Staples and Isaiah Rashad, IshDARR posted his first tracks online, growing an audience while maintaining schoolwork. The Better Life EP surfaced in 2014 and contained the single "POPS" featuring Rina. Atlantic Records took notice, prompting studio sessions with producers Arthur McArthur (Wiz Khalifa, Drake, Lil Wayne) and J. Gramm (Kid Cudi, Travis Scott). Old Soul Young Spirit, his debut album, appeared in 2015 and showcased the Gramm-produced cut "Too Bad." Broken Hearts & Bankrolls, his second full-length release, followed the next year.
