Distinctively gruff and pugnacious throughout his lengthy career, Freeway staked his spot in the post-millennial hip-hop landscape with an appearance beside brethren and on ‘s “1-900-Hustler” (2000). The Philadelphian rapper capitalized on subsequently increasing momentum with one of ‘s most thrilling releases, the Top Ten pop hit Philadelphia Freeway (2003), which featured appropriately energizing productions from and the emergent . Although he recorded only two more solo albums during the 2000s and broke away from , Free continued to grow with a series of LPs throughout the 2010s, including the collaboration The Stimulus Package (2010) and the reinvigorated Diamond in the Ruff (2012). Think Free (2018), a homecoming of sorts, was licensed exclusively to ‘s Roc Nation.

Named after infamous drug trafficker “Freeway” Rick Ross, Leslie “Freeway” Pridgen made himself known as a valuable member of the family. His ascent can be traced back to an agreement he made with fellow Philadelphia rapper . Mutually admiring acquaintances from the same local nightclub, the two fledgling MCs made a pact: the one who first landed a record deal would pull the other along. signed with the subsidiary co-founded by and , and stayed true to his word. Freeway debuted as a featured artist on “1-900-Hustler,” a track off ‘s 2000 album The Dynasty: Roc la Familia. For the next couple years, Freeway stacked guest verses, often beside and , and as part of the group filmed the 2002 crime drama of the same title, promoted with a soundtrack. Inevitably signed to the Roc as a solo artist, Freeway released his first album, Philadelphia Freeway, in 2003. Strengthened by productions from , , and , it entered the Billboard 200 at number five with the Hot 100-scraping singles “What We Do” and “Flipside” among the standouts. Freeway’s next move was with the North Philly group Ice City, whose Welcome to the Hood was independently released in 2004. By the end of that year, Freeway’s secondary discography also included appearances on ‘s “Here Comes the Fuzz,” ‘s “Just Blaze, Bleek & Free,” and ‘s “Two Words.”

After a less prolific period in 2005 and 2006, Freeway released his second album, Free at Last, in 2007. Only returned as a producer, with the likes of , J.R. Rotem, Needlz, Don Cannon, and part of a large cast alternating duties. “Roc-A-Fella Billionaires,” a production featuring , dented Billboard’s R&B/hip-hop chart. The LP almost cracked the Top 40 of the Billboard 200, and like the debut went Top Five R&B/hip-hop. Upon severing ties with his label, Freeway issued the no-frills 2009 album Philadelphia Freeway 2 on the label, and the next year offered the 2010 collaboration The Stimulus Package via . Two years later, amid numerous supplemental mixtapes, Free issued Diamond in the Ruff through , and followed it shortly thereafter with Broken Ankles, an EP made with mash-up specialist . Free Will, part of which was written in response to being diagnosed with kidney failure, arrived on in 2016 as Free’s sixth proper solo album. As he awaited a transplant, he struck a licensing deal with ‘s Roc Nation. The association facilitated the 2018 release of stern album seven, Think Free, on which he was supported by and , as well as and . Free underwent a successful kidney transplant in 2019.