Top 5 Greatest Rappers From Philly
The top 5 list is passionate debate across the board.
Whether you're talking Top 5 greatest athletes of all time.
Top 5 best soccer players.
Whatever Top 5 you want, the debate gets intense.
The most intense Top 5 debate is the greatest rappers of all time. Lotta emotion and strong opinions in this debate. Also a lot of people who don’t know what they’re talking about.
For me, there’s an easy Top 3, the 4th and 5th spot are difficult to pick.
Regardless, I’m taking a slightly different approach to the Top 5 Greatest Rappers list.
It’s the Top 5 Greatest Rappers from Philly.
Let’s get into it.
1. Black Thought
It’s asinine to me if someone doesn’t have Black Thought as their number 1 from Philly.
If they don’t even have him on their list, they aren’t educated enough for me to have a convo with them.
In 1987 he co-founded The Roots, which are known as one of hip-hop's most important and influential groups.
Almost 40 years later he’s still one of the most talented emcees. Many hip-hop critics and blogs consider Black Thought to be one of the most skilled, incisive, and prolific rappers of his time due to his multisyllabic rhymes, internal rhymes, flow, breath control, socially conscious lyrics, and live performances.
Also, very few rappers can get over 18 million views from a 10 minute freestyle.
2. Cassidy
Crazy underrated. He is hip hop culture.
And he’s got the Philly grit.
Some might not consider him a mainstream, radio hit rapper.
I can understand why. He’s very raw.
That said, he has a few albums and singles that placed in Billboard's Top 10 and Top 5.
He’s reached certified Gold and Platinum status.
He’s a very talented, true hip-hop emcee.
Let’s not forget. Back in 2012-13, when almost everyone wanted to give Meek Mill the crown as the best in Philly.
Meek challenged Cassidy to a rap battle for $100,000.
Cassidy accepted the offer, and Meek was too scared to actually follow through.
Rightfully so. As proof in the diss tracks that came after, Cassidy is simply a better rapper.
He easily sits behind Black Thought as the Best From Philly.
This might not be his best song, but it’s my favorite:
3. Beanie Sigel
Initially I had Freeway over Beanie Sigel. Then I switched it. Beanie put too many other Philly artists on, including Freeway. Plus, he’s nice on the mic.
In 1998 Beanie was Jay and Roc-A-Fella’s flagship artist.
He also put Freeway on in a way and contributed to Freeway getting a record deal with Jay.
He also was the leader (along with Freeway) of the Philly based group, State Property.
Regardless of where his albums ended up ranking on Billboard after releasing, he always received positive feedback.
Beanie’s biggest challenges seemed to be label / bandmate drama that happened behind the scenes, and being in trouble with the law. He was arrested at least six times and served a few years in prison.
Dealing with all of that has to impact your headspace and ability to create your best content.
4. Freeway
I think some people would put Freeway above Beanie. Like I said, I initially did.
But I’m not sure if Freeway gets to where he was/is if it wasn’t for Beanie in those early days.
Freeway has some certified classic songs and commercial bangers. Most notably “What We Do” and “Flipside”.
The tone of his voice fully encompasses the Philly vibe.
Also, you can’t go to a hip-hop show in Philly and not see the Philly Freezer. Every hip-hop artist that comes through the city shows Freeway love and brings him out on stage.
To be honest, I was a fan of Freeway before I knew who he was because of his song Flipside in the movie You Got Served. That used to be one of my favorite movies. As a white boy with no dance moves, I saw those guys dancing and thought it was the coolest thing ever.
And Freeway’s song bumps in that movie. Literally the perfect song for that scene.
A few years back I had the chance to meet Free and kick it with him for a few brief minutes.
Me and Freeway after a private screening of his 'Think Free' documentary.
5. Eve
Honestly, Eve could be #2 or #3.
Eve had, and still has, mad dudes reciting her rhymes word for word. Me included.
Her first album topped Billboard 200 and she received double platinum certification. Her first album!
This put her in elite company at the time as one of three female rappers to achieve this status. The other two being Lauryn Hill and Foxy Brown.
Right after dropping the album she did features that placed on the Billboard charts with The Roots and Missy Elliott.
Frankly, many debated Lil Kim vs Nicki as the best female rappers.
I don’t know how Eve is not in that conversation. Circle back to the statement I made above, people don’t know what they’re talking about.
Like for real, Eve had the whole game on lock with this song:
If anyone stumbled across this article and took the time to read it, chances are they feel strongly about some present day mainstream rappers not being included on this list.
You’re not educated if you feel that way.
One is an industry plant who just yells on the mic.
The other isn’t really a rapper. I don’t know what you’d classify him at this point.
Real hip-hop heads will respect this list. They might not agree with the order. I think that comes down to personal preference in some cases. But these are clearly the 5 best, most talented, rappers from Philly.