Lil Bibby

79th and Essex

Brandon George Dickinson was born in Chicago on July 18, 1994, and grew up around 79th Street and Essex Avenue on the South Side. His stage name comes from basketball, and he has said his sister introduced him to rappers such as Nas and DMX before he gravitated toward Lil Wayne and Gucci Mane. He began rapping around 2011, and from the start he worked closely with neighborhood friend Lil Herb, later known as G Herbo.

“Free Crack”

The pair's early collaboration “Kill Shit” drew notice in 2013, including from Drake, who quoted it online and reportedly urged Bibby to finish his mixtape. “Free Crack” arrived on November 29, 2013, with Lil Herb and King L among its guests and production from DJ L, Hit-Boy, Honorable C.N.O.T.E. and Young Chop, among others. His deep, measured delivery set him apart from many drill peers. He was named to XXL's 2014 Freshman Class, and “Free Crack 2” followed on August 29, 2014, racking up heavy download numbers. “Free Crack 3” came out on November 27, 2015. He signed with Kemosabe Records, an RCA imprint, but never released a studio album there.

Grade A Productions

In 2017 he co-founded Grade A Productions with his brother George “G-Money” Dickinson and Peter Jideonwo. The company signed Juice WRLD in 2017, and early the next year the rapper entered a joint venture with Interscope, reportedly worth $3 million. Juice WRLD's rise made Grade A a major force, and its roster later included The Kid Laroi. Bibby has since focused mainly on his role as an executive, making him one of the few first-wave drill artists to build a second career on the business side.

Read the story: Chicago Rap, Decade by Decade: From Hip House to Drill