Five Important Moments in the Career of Philadelphia Freeway


This Monday one of Philadelphia’s favorite sons, Freeway, performs at the Highline Ballroom. One of the most consistent MCs for over a decade, the sheer volume of quality Freeway tracks makes it easy to forget he’s had one of the more interesting career trajectories of any rap artist this millennium. As he preps for the release of his new album Diamond in the Ruff on Babygrande, let’s take a look back at Freeway’s wild ride.

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Jay-Z featuring Beanie Sigel, Memphis Bleek and Freeway – “1-900-HUSTLER” 2000
According his song “This Can’t Be Real,” Freeway first got his big break by “spitting [his] heart out” after a chance meeting with Jay-Z. After a house arrest stint, fellow Philly-native Beanie Sigel kept his promise and got Freeway in the studio with Jigga for his 2000 posse cut “1-900-HUSTLER.” A spiritual sequel to TKO’s 1-800-Ted-&-Kette, Jay apparently told Free he wanted to make the debut special, hence the elevator music before Free’s explosive verse.

Beanie Sigel featuring Freeway – “Roc Da Mic” 2001
After the strong reception to “1-900-HUSTLER,” Sigel decided to enlist Freeway to join him for the first single from his group State Property’s compilation/direct-to-video movie soundtrack. “Roc Da Mic” gave Freeway the platform of an infectious beat to display how varied and versatile his flow truly was, resulting in one of the year’s most memorable hits. With his signing to Roc-A-Fella official, Free was slated to drop his debut album at the peak of the label’s hottest streak.

Freeway – “Goodbye” 2003
Unfortunately for Freeway, his debut album Philadelphia Freeway was released shortly after 50 Cent’s Get Rich or Die Tryin’, rap’s most anticipated debut album in years, which cast quite the shadow. While the album’s most fondly remembered for the Peedi Crakk-assisted Just Blaze-produced single “Flipside”, far more indicative of Philadelphia Freeway‘s struggles was “Goodbye.” A fantastic farewell letter that uses the act of leaving a woman as a metaphor for departing the block, sample issues caused it to be absent from the retail release.

Jake One featuring Freeway & Brother Ali – “The Truth” 2008
After his second album Free At Last became somewhat lost-in-the-shuffle of a post-Jay-Z post-Roc-a-Fella Def Jam, Free parted from the label and planned a “Month of Madness” where he would release a new song every day for 30 days. Just prior to this, he appeared on frequent collaborator, producer Jake One’s compilation album White Van Music for “The Truth,” a duet with underground sensation Brother Ali. Given the strong reception for this track and the Jake One produced joints during the “Month of Madness,” as well as the positive experience with “The Truth’s” release, Free signed to Minneapolis independent label Rhymesayers Entertainment for his entirely Jake One produced album The Stimulus Package.

Freeway & Jake One featuring Raekwon – “One Thing” 2010
The change of scenery did wonders for Freeway, allowing the one-MC one-producer effort to be the most focused release of his career. Working with Rhymesayers not only allowed Freeway to be exposed to an entirely new audience, but gave him the freedom to make an album free of the pressures and compromise of the major-label system. Freeway and Jake’s chemistry was off-the-charts, resulting in tracks like the Raekwon-assisted “One Thing.” As a bonus, the album’s packaging (a CD-sized wallet complete with dollar-bill linear notes and a credit card with codes for downloadable instrumentals) remains one of the most inventive physical releases of the past decade.
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