In the 80s and 90s, Philly was known for producing some of the top DJs in the culture. DJs like Cash Money,  Miz and Jazzy Jeff set a standard that put “The City of Brotherly Love” on the map. If you were looking for a technician on the wheels of steel, you knew what city on the East Coast had them. Then the millennium rolled around, and Philly started to be known for something different. People started to finally zone in on the plethora of dope emcees being bred on those cheesesteaks, water ice, and Frank’s sodas.

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READ MORE: Beanie Sigel Ft. State Property; The Reunion

Roc-a-fella was one of the first to put a spotlight on these local rappers.


When they cultivated a crop of young lyricists, later known to the world as State Property, the Hip-Hop world took note. A movie, a clothing line and a new way of thinking and rhyme-flipping distinguished Philly from the pack of newbies cracking open the 2000s. A North Philly rapper by the name of Freeway was one of this crew’s top gunners.

Roc-a-fella was not alone.

Another Hip-Hop empire out of New York, Ruff Ryders, also identified Illadelphia as an incubator for rap music gold. They tapped a sexy shorty doo-wop to be the darling of their crew named Eve. Eve came to the table, the pit bull in a dress, and did what few femcees have ever done at the time: She crossed over. But she also did that with the support of a whole team behind her. Features galore, she merged glamour and bars each time she took the mic. But there also was another: Cassidy.

READ MORE: The Ruff Ryders Announce a Reunion Show

When Cassidy signed to Ruff Ryders, he provided them with a different energy that shifted the Yonkers/ Bronx heavy energy that the label once had.

And this is where the magic starts.

The year was 2001 and Roc-A-Fella was on top of the world. The year prior, The Roc dropped Beanie Sigel’s classic The Truth, Memphis Bleek’s The Understanding, a compilation record with DJ Clue? and an album with Amil. 2000 proved to be a bankable year for The Roc, particularly with JAY-Z leading the pack with a record that introduced State Property to the world, The Dynasty: Roc La Familia. This set up 2001 for an especially amazing year.

READ MORE: Neef Buck Dropped “Forever Do Me”; Album ft. Dave East, State Property & More

Clue? dropped another record. As did Beans… and history will reflect that JAY-Z solidified himself as an icon by releasing The Blueprint (let that breathe) and a live record with the illy Philly band, The Roots entitled JAY-Z: Unplugged. Needless to say, Jay and Dame were stunting all over the place. And everyone wanted them… especially Hot 97’s number one radio DJ and tastemaker, Funkmaster Flex.

With an exclusive invitation up, The Roc took over the Flex show and one of the stars of the night was Philly Freeway. For almost 45 minutes, Freeway and his crew lit up the airwaves with bars after bars after bars. He killed it. But that might have bitten him in the butt in the end.

The freestyle was a break from recording State Property record that included the entire crew: Beanie Sigel, Freeway, Young Chris, Oschino, Neef Buck, Omillio Sparks and Rell. That album produced 2002 classic “Roc the Mic” that til this day sets it off.

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The energy around this night and the work that everyone knew was coming just a few months later, had JAY-Z on the phone (according to Freeway) stunting on Swizz Beatz.

While Freeway does not remember what was said, he did know that after that night they went back to the Bassline Studio for a quick moment to recoup. But shortly afterward, he was whisked to another studio for another session. JAY-Z was like “Let’s go!”

They arrived at this studio and was met by Swizz Beatz, some members of The Lox and Cassidy (their new guy). Freeway says of that night:

“That was how it was back then. At any time, you would be called to battle. You had to be prepared to rap at any second. It didn’t matter where or who.”

When he walked in the room, he didn’t know Cassidy by face. But he “knew his name.”

“We knew who each other were. I knew him because he had a name for himself. He would call up Power 99, the radio station in Philly, and he would win all the freestyle contest on the air. There wasn’t social media like it is now and so, I didn’t know what he looked like. But I knew his name.”

Freeway and Beans had been battling all over the city. So it was likely that Cassidy, who is younger, would have known about them also. In fact, they duo built them chemistry organically on the Philly battle circuit. Their first battle together was at a local teen club promoted by Philly legend Bobby Dance called “Dances.”

“I was in the crowd and was like let me rock with you. We been cool every since.”

But Cass and Free seemed to be on the opposite parts of each other’s world. Cass was at Central High School (one of the top schools in the city) and Free was in the cut. Without social media and acute geographical and neighborhood bias, their circles would not have met up.

“I believe the boah was from somewhere Uptown and I am from North Philly.”

Back to the studio… From The Roc, Beans, Chris and Freeway were repping. JAY picked Free.

And thus the history was made.

First Round: Cassidy rapped for a little over 1 minute. Freeway did almost 2.5 minutes.

Second Round: Cassidy rapped for a little over 2 minutes. Freeway did a little over 1 minute.

Third Round: Cassidy rapped for a little over 1 minute. Freeway did a little under 2 minutes.

Forth Round: Cassidy rapped for 1 minute. Freeway did a little under 2 minutes.

Fifth Round: Cassidy rapped for a little over 1 minute. Freeway did 2 minutes.

Sixth Round: Cassidy rapped for almost 2 minutes and the battle ended with Freeway asking for a beat to drop.

Freeway without doing a 6th round, rapped 52% of the battle.  To that point, some of his rhymes were from the early freestyle on the radio.

“I don’t want to sound like I am making an excuse, but I had been rapping all day. I don’t know what he was doing. After a while, I just went into my bag.”

Had he not been on Flex earlier, he would have probably had the rhymes in tow to go longer. Not only that, you can see there was a different mind frame that Freeway was in during this season. He was not focusing on battling, but more focused at the time being prepared for the freestyling that lead to a check. Also stylistically, they were different.

“Cassidy had more punchlines and personal disses. As a rapper, I speak more personal, dealing with my reality and truth.”

It is true. As you watch the battle, Cassidy has a style most similar to battlers that break down and comes at their competition like a Lux, Mook, dare we say Goodz. Cassidy for all practical purposes is an opponent driven rapper, a style that is great for this current incarnation of battlers. Freeway, on the other hand had content that look at the complexity of urban life like a Shotgun Suge, Chess or T-Top.

READ MORE: Cassidy Returns to the Stage, But Remember When He Battled Freeway?

The vibe was intense that night, but what could be said was a victory for the hometown is that these two Philly rappers were the leading snipers for these big New York based rap crews. Paving the way for others like Meek Mill to take his place in the landscape of Hip-Hop elite… and for people like Troy “Smack” White.

“Cassidy says that he basically started Battle Rap. I mean, then I can say that too. Smack and I have been friends forever and I freestyled and rhymed for him back in the day. Smack was every where getting every body rapping.”

“What they are doing now in the Battle Rap is incredible! I follow it.”

Some of the artists that Freeway actually likes may blow your mind.  As a follower, of course, he loves those who are typically on people’s Mt. Rushmore like Murda Mook, Lux, Hollow Da Don and Arsonal. But he also has a great appreciation for new stars like Geechi Gotti, Ave, Nu Jerzey Twork, Rum Nitty and T-Top. He not only is a fan, but friends with Brizz Rawsteen and Shotgun Suge. Two others that he keeps his eye on are John John Da Don and Tay Roc.

“I might come down if my schedule allows. I got a few shows around that time. If I can’t make it, I don’t have a problem buying the pay-per-view.”

READ MORE: Cassidy Returns To Battle Rap Vs. Goodz on SMACK/URLTV

Though Free is out on the road promoting his new album Think Free, the now Roc Nation artist shares a little more about commercial rappers that battle that simple was not captured on tape.

“I saw Cam’ron battle Tommy Hill. Cam won.”

Tommy Hill was another Philly flame-spitter and one of the founding members of the R.A.M. Squad, who was shot down and killed in 2011.

He also had a crazy battle with Queens Bridge vet, Cormega.

“Mega will probably say something different, but I won that one.”

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