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

Named after infamous drug trafficker "Freeway" Rick Ross, Leslie "Freeway" Pridgen made himself known as a valuable member of the Roc-A-Fella family. His ascent can be traced back to an agreement he made with fellow Philadelphia rapper Beanie Sigel . 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. Sigel signed with Roc-A-Fella , the Def Jam subsidiary co-founded by Jay-Z and Damon Dash , and stayed true to his word. Freeway debuted as a featured artist on "1-900-Hustler," a track off Jay-Z 's 2000 album The Dynasty: Roc la Familia. For the next couple years, Freeway stacked guest verses, often beside Sigel and Jay-Z , and as part of the group State Property filmed the 2002 crime drama of the same title, promoted with a Roc-A-Fella soundtrack. Inevitably signed to the Roc as a solo artist, Freeway released his first album, Philadelphia Freeway, in 2003. Strengthened by productions from Just Blaze , Kanye West , and Bink! , 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 Mark Ronson 's "Here Comes the Fuzz," Memphis Bleek 's "Just Blaze, Bleek & Free," and Kanye West 's "Two Words."

After a less prolific period in 2005 and 2006, Freeway released his second album, Free at Last, in 2007. Only Bink! returned as a producer, with the likes of Cool & Dre , J.R. Rotem , Needlz, Don Cannon, and Jake One part of a large cast alternating duties. "Roc-A-Fella Billionaires," a Dame Grease production featuring Jay-Z , 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 Real Talk label, and the next year offered the 2010 Jake One collaboration The Stimulus Package via Rhymesayers . Two years later, amid numerous supplemental mixtapes, Free issued Diamond in the Ruff through Babygrande , and followed it shortly thereafter with Broken Ankles, an EP made with mash-up specialist Girl Talk . Free Will, part of which was written in response to being diagnosed with kidney failure, arrived on Babygrande in 2016 as Free's sixth proper solo album. As he awaited a transplant, he struck a licensing deal with Jay-Z 's Roc Nation. The association facilitated the 2018 release of stern album seven, Think Free, on which he was supported by Fat Joe and Lil Wayne , as well as Faith Evans and BJ the Chicago Kid . Free underwent a successful kidney transplant in 2019.