In 1998, the mainstream Hip-Hop landscape was dominated by No Limit soldiers, Bad Boys, and Wu-Tang killer bees. There was a preoccupiation with floss and, in the wake of the high-profile murders of 2Pac and the Notorious B.I.G., the industry seemed to want to shine as much as possible. Understandable — but out of Yonkers, N.Y., there came a crew. With a production wizard, a brash beauty, a trio bred from the streets, and a tortured superstar who was taking the rap game by storm, the Ruff Ryders put the streets squarely on the late 90s pop charts. In doing so, they helped usher in the new millennium of East Coast hardcore: grimy enough for the hood; polished enough for the charts. They owned the streets and the radio. Here's 20 of their best bangers.
Jada and Eve pull off the classic "Battle of the Sexes" with this stellar back-and-forth over a steel drum-driven beat from Teflon. Released a single from Ryde Or Die, Vol. 2, it revived a classic pop music formula (seriously, everybody from Otis Redding and Carla Thomas to Ice Cube and Yo-Yo have done it) for the hardcore bling era.
The surging beat is one of the most anthemic X ever rhymed over, and his aggression belies a tour-de-force performance that caps the tail end of DMX's most classic run. The kiddie chorus is the right kind of foreboding: both a warning and a call-to-arms.
Kiss and The LOX had been well-established by the time he released this declaration of self. It's a showcase for his particular brand of pensive street rap and lyricism, a pronouncement more than an announcement. And proof positive that Kiss has a lane all his own.
By 1999, the whole world knew who this guy was. But X's hunger was still palatable in every single. Even as the vids got glossier and the collabos got Sisqo-ier, X managed to bring grittiness to hip-hop's surging mainstream over a skittering backdrop by Irv Gotti & Co.
She'd begun her career on Dr. Dre's Aftermath, but we didn't really get to hear what E-V-E could do with the Good Doctor (and Scott Storch) until this monster hit from the early 00s. Paired with soon-to-be-solo superstar Gwen Stefani, the Philly rhymer delivered a bouncy single that still seems to capture the best of its era.
One of the best examples of DMX's tortured brilliance, the autumnal sadness of this classic perfectly conveys the hopelessness and vulnerability in X's verses. He's an artist who came to embody "write your pain," and this single from his second album is proof positive that few wore angst better.
An examination of domestic violence that lingers long after that first listen, Eve's heartfelt single was dedicated to her high school best friend. The Ruff Ryders' First Lady struck back for victims everywhere — and struck a chord with anyone who'd endured, known someone who'd survived, or had lost someone to the pain of abuse.
DMX was on quite the singles run, Sisqó was at his post-"Thong Song" peak and over a slinky beat that could only come from Nokio, X rattles off his frustrations as a gruff ladies' man. The infamous name-dropping of "Brenda, LaTisha, Linda, Felicia..." made it one of the most quotable tracks in X's oeuvre and birthed a viral internet challenge almost 20 years after its release.
Swizz's inspired flip of Freda Payne is the perfect backdrop for Styles P's ode to herbal refreshment. The hit leadoff single from his A Gangster And a Gentleman album, the track was close to inescapable in 2002; turning up everywhere from Swizz's own compilation to the Kevin Hart comedy Soul Plane.
It sounded like a warning, issued from a newcomer ready to take on the flossy chart-toppers dominating the rap game. DMX had a few major hits under his arm when he unleashed this anthem, letting everybody know, regardless of where you stood in hip-hop's hierarchy, you were going to have to contend with the dark rhymer's hunger.
Over soulful production from Mobb Deep's Havoc, Jadakiss poses the hood's hardest questions. It proved to be one of his most resonate tracks, and it's not hard to see why. Referencing everything from the prison industrial complex to the early 2002 Oscar race, it became a smash hit in the summer of 2004, skyrocketing all the way to No. 11 on the Billboard Hot 100.
NYC-based rap labels were enjoying a friendly competition in the commercially lucrative late 90s. Roc-A-Fella and Ruff Ryders were two of the hottest brands in Hip-Hop. Jay-Z and Roc-A-Fella understood how to walk the balance between ballerific raps and street grit. Hov pairing with Ruff Ryders made all the sense in the world circa 1998.
It became a phrase that defined Bonnie & Clyde-esque solidarity for a generation. And it was the single that announced The LOX's second act, as the street rap trio had landed on Ruff Ryders after a highly-publicized departure from Puff Daddy's Bad Boy Records. The Timbo-produced track made it clear the trio from Yonkers could craft radio hits and keep it street.
An epic single that served as the first solo hit from Jadakiss, this street anthem (has any song ever epitomized that phrase better?) is one of the best in Ruff Ryders' enviable oeuvre. Alchemist laced Kiss with one of his most inspired beats, and Jadakiss delivers as only he can: the kind of rabble-rousing call to arms that resonated on many a corner.
There had been odes to thug love before, but none had managed to be so cute, so sweet and so street — all at the same time. Eve's brand of everygirl relatability was unique in the high glamour late 90s, but make no mistake — nobody could blend swagger and sex appeal like the Ruff Ryders First Lady. The kind of song that made many a thug wish they had this sorta girl by their side.
Sometimes you just know an artist is in their element, and just enjoy watching them work. The LOX were, in many ways, the soul of Ruff Ryders. The grimy street tales from the Yonkers trio were always a better fit for Ruff Ryders than Bad Boy, and Sheek Louch, Styles P and Jadakiss do what they do best on this melancholy masterwork from TJ Beatz.
Everybody knew Dark Man X was coming. He’d been making noise via underground performances and several scene-stealing appearances on hit singles by Ma$e and LL COOL J for almost two years. But his first major label single dropped like a grimy bomb in a landscape littered with shiny suits. With his first hit, X made it clear who he was, and also made it clear that the game wasn’t going to drown in jigginess as we raced towards Y2K.
Proof positive that nobody does synth-driven fanfare better than Swizz, this epic single gave Drag-On a huge boost leading into his solo career and was one of the few late 90s East Coast/Dirty South collaborations that didn't’ feel forced or awkward. Juvie repped for NOLA’s Cash Money and, circa 1999, this was the two hottest new labels in the rap game joining forces.
She finally had her moment. The "Illest Pitbull In A Skirt" had been waiting in the wings for almost three years, but it was this catchy, salsa-inflected single from the Ryde Or Die Vol. 1 compilation that not only let the world know the Philly firebrand had arrived, but made it clear the RR was taking over the radio.
Could there be any doubt? The song that all but announced the genius of Swizz Beatz, its an anthem in every sense: instantly memorable; a call to arms for the crew; and a song that transcends its time and era. It's the label's theme song, and captures a moment in time that feels immediate and fresh every time you hear that infectious chorus -- but it never feels stuck in 1998. It's a street rap masterpiece. And to think, X didn’t even like the beat when he first heard it.
* Banner Image: DMX performs during the Ruff Ryders Reunion Concert at Barclays Center iin New York City. (Photo by Johnny Nunez/WireImage)