Westside Gunn released his first mixtape in 2005, however his career was derailed by run-ins with the law. Gunn served time in prison from 2006 to 2008 on a weapons charge, and again from 2010 to 2011 for a parole violation. Gunn did not release any music in the years 2006-2011.[2]

In 2012, Westside Gunn co-founded the Griselda Records label with his brother Conway the Machine and Mach-Hommy.[3] Gunn was inspired to revitalize his career by the shooting of his brother Conway that same year, which left him with permanent disabilities, as well as by the 2006 murder of his cousin Machine Gun Black. Gunn’s first project for Griselda was the mixtape Hitler Wears Hermès. While the name attracted controversy for its reference to Adolf Hitler, Gunn explained that the name is a play on The Devil Wears Prada.[4]

Over the next few years, Gunn released a steady stream of mixtapes and EPs, including multiple sequels to Hitler Wears Hermès, on the Griselda label. Gunn’s official studio album debut was Flygod, released on March 11, 2016.

On March 3, 2017, Griselda Records signed a deal with Eminem's Shady Records, making Westside Gunn and Conway the first rappers from Buffalo to sign with a major label.[3] After signing with Shady, Gunn played at Coachella, Firefly and Governors Ball.

[5] On October 2, 2020, Westside Gunn released his Shady Records debut, Who Made the Sunshine, his only solo project with Shady Records.

Shortly after signing with Shady Records, Westside released Flygod Is Good... All the Time, as a collaborative EP with producer Mr. Green.[6] Ambrosia For Heads named 2018's Supreme Blientele one of the best albums of 2018.[7] He also signed with Roc Nation alongside label mate Benny the Butcher on August 6, 2019, under a management deal.[8]

On April 17, 2020, he released his third studio album, Pray for Paris. The album has features from artists such as Tyler, the Creator, Wale, Joey Badass and Freddie Gibbs.[9] On July 3, 2020, Westside Gunn released his tenth mixtape Flygod Is an Awesome God II, the sequel to his July 2019 mixtape Flygod Is an Awesome God. The album features guest appearances by frequent collaborators Benny The Butcher, Keisha Plum, Boldy James, and Daringer.[10]

On November 14, 2020, in an interview with Joe Budden, Gunn announced he had fulfilled his contractual obligations to Shady Records and had become an independent artist. [11]


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