Emerging from the Chicago hip-hop scene with a fiercely lyrical and aggressive style, Montana of 300 established himself as a formidable independent force in the genre. Born Walter Anthony Bradford on March 3, 1989, in Chicago, Illinois, he was raised in Peoria and later returned to Chicago, experiences that deeply informed his gritty narrative-driven music. His stage name, Montana of 300, originated during his high school years when he formed the hip-hop collective simply called 300 alongside his friend Talley of 300, a name reflecting both the Spartan imagery of the film 300 and the area code of their Chicago roots.

Montana of 300 first garnered significant attention through a series of viral freestyles and remixes posted online, most notably his 2014 "Chiraq" remix of Nicki Minaj's "Chi-Raq," which showcased his rapid-fire delivery and intense wordplay. This online buzz translated into commercial success with his debut studio album, Fire in the Church, in 2016. The project was a critical and fan-driven hit, entering the Billboard 200 chart and solidifying his reputation as an artist who could thrive outside the traditional major-label system. He cultivated a dedicated following by maintaining a prolific and consistent release schedule.

He developed a unique tradition of releasing new albums on May 20, a date whose personal significance he kept private. This series included Don't Doubt the God (2017), Pray 4 the Devil (2018), A Gun In The Teacher’s Desk (2018), and Views from the General's Helmet (2019). Each project further explored his signature blend of drill-influenced production, complex rhyme schemes, and themes of street life, faith, and perseverance. After several delays, Montana of 300 released his sixth studio album, Rap God, in 2022. Upon its release, he announced that the album would be his final, marking a potential conclusion to a distinct chapter in his career. Throughout his journey, Montana of 300 remained a prominent example of an artist who built a sustainable career through direct fan engagement and a uncompromising musical vision.