On this day, April 27, in hip-hop history...

Ruff Ryders/Interscope Records
Ruff Ryders/Interscope Records

1999: On April 27, 1999, Ruff Ryders Entertainment made their full introduction to the rap game as a family when they dropped their first compilation album, Ryde or Die Vol. 1.

Founded by Joaquin "Waah" Dean and his brother and sister, Darin "Dee" Dean and Chivon Dean, the label featured rappers like the ascendant DMX, The LOX, Drag-On and Eve throughout the years. With the talented roster at their back, Ruff Ryders was poised to help fill up a space in the rap world following the tragic deaths of two rap superstars.

"With the loss of Biggie and the loss of Tupac [Shakur] left a void, and that void opened the door for hip-hop," Waah tells XXL. "So for us to get in because everybody was like, 'What's next?' We feel like we brought a new, fresh airwave into the game."

Bringing that new airwave to the game took some time. Waah says it took 12 years of grinding before Ruff Ryders got their proverbial break. The process was aided by the success of DMX, who'd signed to Ruff Ryders first and then Def Jam in 1997.

"Basically, I discovered DMX and pulled everybody into the fold," Waah shares. "Then, I took a couple of my producers, one of my producers and A&Rs, [Irv] Gotti, he got a deal with Def Jam as an A&R. From there, he pretty much opened the door for us to come in with DMX on Def Jam. We put that Def Jam deal together."

Entertainment One
Entertainment One

After signing with Def Jam in 1997, DMX, who'd already been on Ruff Ryders, released his debut album, It's Dark and Hell Is Hot in May of 1998, and his follow-up, Flesh of My Flesh, Blood of My Blood, in December of that same year. Both albums went multiplatinum and helped show the world that Ruff Ryders was the real deal.

Still, despite the success that came with Ruff Ryders' production deal, they didn't have the label deal to release a compilation project. Waah says Def Jam had so many other projects from artists on their roster that they had too many to handle at the time, so Ruff Ryders couldn't secure a label deal with them. He says it was a call from Diddy—then known as Puff Daddy—that helped Ruff Ryders align with Interscope Records, the label that ultimately released Ryde or Die Vol. 1 along with Ruff Ryders in 1999.

"Puffy cosigned us with Jimmy Iovine," he says. "We went over there to do our label deal with Interscope. And then meanwhile, our moment of things being on fire and putting the heat out there on DMX and we put our Ruff Ryders label in Interscope with Ryde or Die, Vol. 1 was our introduction from the world from the label."

With the Interscope label deal in hand, the Ruff Ryders were ready to ride. According to Waah, Ryde or Die Vol. 1 was created during a time when Ruff Ryders artists were recording an album's worth of material every 15 days. However, in an era before emailing audio files for cross-country recording sessions wasn't as popular or as readily available an option, he notes that orchestrating the collaborations lengthened the process of making Ryde or Die Vol. 1.

"We didn't have social media, we didn't have Pro Tools and stuff that you could just record and then send the vocals all the way across the other world and you could see each other on camera," says Waah, who reveals that connecting with artists like Big Pun and Juvenile led to the album taking 40 or 50 days to be completed. "You had to physically be there to do it. So we didn't have that luxury."

Once artists were able to make it to the studio, they found an embodiment of the streets of New York. "It was like 42nd Street on steroids inside the building," Waah recalls. "You got Lox session, all they crew, coming in and doing a session. You had Ma$e coming through. You had our own crew. You had people from the whole city of New York in those sessions...they was in there gambling, doing all kinds of stuff ’cause it was a street vibe." For Waah, the set-up was all too appropriate. "We made music for the street."

With heavy production from Swizz Beatz, the record label's stars went bar for bar on thumping gangsta rap beats. Features from the likes of Jermaine Dupri, Juvenile and Big Pun add some new flavor to the Ruff Ryders team, but the label's signees were the ones who proved to be the biggest winners from the LP. The album's title song "Ryde or Die" is a posse cut featuring Jadakiss, Styles P, Sheek Louch, Drag-On, Eve and DMX. The track established both Eve and ’Kiss as forces to be reckoned with, as Eve asserts herself as the First Lady of Ruff Ryders and Jada flexes his lethal mic skills.

Other standouts on the album include Jadakiss' "Kiss of Death," Eve and Nokio's "What Ya Want" and of course, Jay-Z's "Jigga My Nigga," which would go on to be a hidden track on Jay's Vol. 3... Life and Times of S. Carter later that year.

The Ryde or Die Vol. 1 album proved to be a huge success, debuting at No. 1 on the Billboard 200 albums chart before being certified platinum on June 2, 1999. By that point, it was clear Ruff Ryders were doing something right, and they were doing it on their own terms.

"We brought a whole different element," Waah affirms of Ruff Ryders' contribution to hip-hop. "The bikes, the cars, the real lifestyle. We introduced what a real lifestyle really means coming from our culture in hip-hop. Every element of it. So, that album really represents the culture of hip-hop, it introduces it to our point of view."

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