Originally hailing from Philadelphia, Pennsylvania, he first gained recognition after appearing on Jay-Z's fifth album, The Dynasty: Roc La Familia in 2000.

[1][2] In 2009, Pridgen was briefly signed to Cash Money Records, although his next three albums: Philadelphia Freeway 2 (2009), Diamond in the Ruff (2012), and Free Will (2016) were released independently.

[3] He returned to work with Jay-Z in 2018, signing to his successor label Roc Nation to release his sixth album, Think Free in June of that year.

Freeway began his career by participating in freestyle battles in his high school and met fellow Philadelphia native Beanie Sigel, while rapping on stage at a hometown nightclub.

In 2001, he underwent a notorious freestyle battle with then-unsigned rapper Cassidy, hosted by Swizz Beatz and lost with a unanimous judges decision.

The album was produced primarily by Roc-A-Fella-affiliated beatsmiths Just Blaze, Bink!, and Kanye West and featured a large number of Roc-A-Fella rappers.

After Jay-Z's "retirement" album and the uncertainty over what direction the label was headed, Beanie Sigel was convicted and jailed on a charge of attempted murder.

[8] With uncertainty in the air, Freeway put together another Philadelphia-based crew called Ice City, named after their North Philly neighborhood.

[11] In response to a crisis of faith, Freeway went on hiatus for a few years, making his Hajj, a journey to the holy city of Mecca, required by every Muslim at least once in his or her lifetime if they are able.

[17] The songs, featuring input from Phoe Notes, Erick Sermon, Don Cannon, Cardiak, Jake One, Oddisee and others, were later compiled into a mixtape.

[18] The year 2009 brought an announcement that he would be working on his third album amidst his regrets over hearing Jay-Z had stepped down as Def Jam president.

[22] Freeway also made an original song "Car Jack" for the 2009 game Grand Theft Auto IV: The Lost and Damned.

[24] Freeway released his mixtape "The Beat Made Me Do It" on November 13, 2009, which featured production by veteran producer Jake One with assistance by Don Cannon to officially announce his 2010 Rhymesayers debut album The Stimulus Package.

[28] In addition to the new clothing line, Free also announced an album called Diamond In The Ruff which featured production from Jake One, Bink!, Needlz and Just Blaze.