Chicago rapper Montana of 300 built his audience by freestyling over beats from other artists’ hit songs. This success gave way to a widely recognized catalogue of original songs. • Montana is from Chicago’s Low End neighborhood. He witnessed a murder at age nine—an experience he recalls in his 2019 song “Monster”. • After watching his mother battle crack cocaine addiction, Montana decided to avoid drugs and alcohol. • His father introduced him to rap music. He’s credited DMX, 2Pac and Lil Wayne as being his biggest inspirations. • In 2008, Montana, Talley and other friends formed the crew 300, named after the Zack Snyder action film. • Montana of 300 freestyled over songs by DeJ Loaf, Rowdy Rebel, Post Malone and Nicki Minaj, earning millions of streams in the process. • His 2017 roughneck love song “Wifin’ You” and its video have surpassed 100 million combined streams. The chorus showcases Montana’s melodic singing.