Few voices are as synonymous with the gritty, cinematic intro of Roc-A-Fella Records as Pain In Da Ass. Before Jay-Z became a billionaire mogul and Rock & Roll Hall of Famer, a teenage Pain was in the trenches of the fledgling label’s headquarters, handing out cassette snippets and unwittingly auditioning for a permanent spot in hip-hop history.
During a wide-ranging conversation, the legendary vocal impressionist and Roc-A-Fella alum pulled back the curtain on the early days of Reasonable Doubt, the relentless hustle of Damon Dash, the truth behind the label’s eventual split and why a Verzuz between Jay-Z and Nas should strictly pit their debut classics against one another.
From Street Team Intern to the ‘Reasonable Doubt’ Intro
In early 1996, independent artist-owned labels were an anomaly in the music industry. When Pain joined Roc-A-Fella as a 16-year-old intern, the office felt less like a corporate suite and more like a neighborhood corner where Jay-Z, Damon Dash and Kareem “Biggs” Burke handled day-to-day operations firsthand.
“I started interning there and Jay would be up there every single day,” Pain recalled. “It’s his label. He’s running the day-to-day operations along with Damon and Biggs. So it was very much hands on. I was dealing with them on a daily basis and this album was in the works.”
Out on the street team, Pain passed out promotional tapes featuring early versions of “Dead Presidents,” “Feelin’ It,” “Can I Live” and an alternate, battle-ready take of “Can’t Knock the Hustle.” Already a fan of Jay-Z’s earlier work on “Can I Get Open?” and the Jaz-O remix of “In My Lifetime,” Pain immediately recognized that Jay was operating on the same tier as The Notorious B.I.G. and Nas.
At the time, Pain was channeled into gangster films, doing vocal impressions around the office to vent his own frustrations. Instead of showing him the door, Jay and Dame embraced the raw energy.
“I became sort of the ‘rally crier’ for the label and also at the time I was watching a whole lot of gangster movies so I was doing a lot of those characters while I was being aggressive,” Pain explained. “I think he [Jay-Z] was a big fan of those movies himself and he saw something in me that I didn’t know that I had and the momentum started and they were like,‘Yo. We gotta let that kid start the album, man! You gotta let him be on the album doing the crazy stuff that he’s doing here at the record company!’”
Damon Dash’s Relentless Grind and the Roc-A-Fella “Dream Team”
When asked about comparing Jay-Z and Damon Dash to Michael Jordan and Scottie Pippen, Pain broadened the analogy to an entire championship roster, crediting Dame’s unmatched work ethic alongside Irv Gotti, Ty-Ty, Bee-High and Biggs.
“Damon just didn’t have double roles. He had quadruple, penta, octo roles!” Pain laughed. “They were promoting Roc-A-Fella and going to the clubs and buy out the bar; Damon’s there buying everybody drinks. I’m 16 years old and I got a champagne bottle in my hand and he’s performing on the stage with Jay-Z. So four or five in the morning I go home and I get to go to sleep and I go to school and when I come in at 2 o’clock in the afternoon, Dame had already been in the office. He slept in the office from the night before and he’s conducting business.”
Despite managing diabetes and serving as both manager and CEO, Dash still found time to debate marketing ideas with his teenage intern—a dynamic Pain views as the ultimate sign of mutual respect.
“When Dame is arguing with you, he’s giving you respect,” Pain noted. “Damon Dash? The smartest. Businesswise and he’s so versed in other things too. He’s great and he’s one of the greats.”
The Truth About the Jay-Z and Dame Split—and Pharrell’s Hall of Fame Tribute
While outsiders often frame the eventual dissolution of Roc-A-Fella as a bitter feud, Pain views it through the lens of champions like Shaquille O’Neal and Kobe Bryant who simply conquered their shared goal and grew in different directions.
“Damon wanted it for Jay maybe more than Jay-Z wanted it for himself,” Pain said. “Jay is Damon’s son’s godfather, you know what I mean? So they’re ALWAYS connected and I don’t think there was a falling out. I think there’s a misconception or perception of that story because as we see, Jay shouted out Dame in his Hall of Fame induction speech.”
That 2021 Rock & Roll Hall of Fame induction also delivered a full-circle moment for Pain. Questlove originally reached out to have Pain perform his iconic Reasonable Doubt skit for the ceremony’s tribute video, and though scheduling conflicts prevented Pain from filming it, watching Pharrell Williams recite his lines alongside tributes from Barack Obama, Beyoncé and Samuel L. Jackson left him floored.
“Pharrell does my part and I’m like, ‘OH WOW!’” Pain said. “It’s funny because it’s not one of his lines; it’s not his lyric but it’s VERY MUCH associated with his career and that’s an honor to me.”
The Ultimate Verzuz: ‘Reasonable Doubt’ vs. ‘Illmatic’
If Jay-Z ever steps onto a Verzuz stage, Pain knows the exact matchup hip-hop deserves: not a sprawling battle of 20-year catalogs, but a heavyweight clash between Reasonable Doubt (1996) and Nas’ Illmatic (1994).
“I want to see the Main Event! I want to see Reasonable Doubt vs. Illmatic. THAT right there would be a Verzuz for me,” Pain declared. “Give me the bibles against each other.”
Breaking down the hypothetical showdown, Pain compared the two masterpieces to Brian De Palma’s classic crime films—framing Nas’ debut as the hungry rise of Scarface and Jay-Z’s as the seasoned, reflective exit strategy of Carlito’s Way.While acknowledging Illmatic’s all-star production lineup of DJ Premier, Large Professor, Pete Rock and Q-Tip against Reasonable Doubt’s backbone of Premier, DJ Clark Kent and Ski Beatz, Pain ultimately leans toward his former boss.
“I would give the edge to Jay only because his ‘been there, done that’ mentality worked well and meshed well on that album,” Pain concluded.
Three decades after handing out snippet tapes on the streets of New York, Pain In Da Ass remains one of hip-hop’s sharpest eyewitnesses, preserving the authentic spirit of an era that changed music forever.
