Reggie Ossé – Living inside and outside of the Hip Hop Revolution
A couple of months ago I was walking in midtown Manhattan, and I walked by this bus stop billboard that stopped me in my tracks. It was an ad for CNN, championing their new on-air lineup, and the headline said: Allow Us To Reintroduce Ourselves, which I instantly recognized as a direct quote from a a Jay Z song entitled, “Public Service Announcement.” Now as I made this recognition, upon further inspection of this ad, it hit me that this ad, the lineup, was blaringly non-diverse—and I want to say what’s up to the brother over there, in the corner, what’s going on sir?
So I’m looking at this ad which is non-diverse and they’re quoting Jay Z, and I’m like, “Why bother?” And then I even ask further, even though people like myself in the know would make the connection between CNN and Jay Z—did CNN’s intended audience, would they even make that connection? So, as an attorney-turned-author, and turned online personality, over the past 40 years, I’ve seen hip-hop evolve from being a fad, to a subculture, to a major force that continues to feed pop culture around the world. And as I watch this evolution, there also seems to be a trend that those who have contributed, or have created this culture, continuously remain on the outside.
I remember years ago, growing up in New York City as a teenager, in the 1980s—this is before rap music became rap records, and this is before rap records became rap videos—this is way before the group Sugar Hill Gang created their seminal hit, “Rapper’s Delight”—are you guys familiar with “Rapper’s Delight?” Sugar Hill Gang is credited as creating the first official hip-hop record. But I remember at that time, me and thousands of other kids from New York City being in lock-step with this emerging culture. It was a very organic time, and we were trying out this new way of being, this new sensibility, this new sense of cool, and the most important thing is it had to be authentic, it had to be original, and you and to be fresh, and fresh means cool.
Now, at the same time, the most important thing we were developing is a new way of language, a new way of speaking. We were trying out different words, like fresh, like dope, like def, like ill, like chill out. It was a great time to be alive in New York City because we were on ground zero of the evolution of a culture that was alive and flourishing.
So, at the time I was in high school I attended St. Francis Xavier High School, located on 16th street between 5th and 6th Avenues, and there weren’t that many people of color at St. Francis Xavier. And I remember one time before class I was clowning around with one another student, and I had to get to class and he wanted to keep clowning around and finally out of frustration I was like, “Yo chill out!” And I momentarily forgot my environment, and lapsed from my practice of code-switching, which is speaking one way in a predominantly black environment, and one way in a predominantly white environment.
So I said “chill out” and it was a group of white students that picked up on my term and it was obvious that they had never heard the term before. So they started mocking me. “Chill out,” and the term was so funny and foreign and they were like, looking at me with disdain, and I felt so sorry for them because I was like, you don’t even know what this is and you are not so fresh.
So years later I shudder when I hear how the term “chill out” has mutated into “chillax” or “chillll” and I marvel at how this word has become so common, so popular. It seems to me as if that term has been around for hundreds of years, and I never would have predicted that this would have happened back in the 80s, when this term was so foreign and so humorous to some.
Getting back to the Sugar Hill Gang: my initial indoctrination to hip-hop music was in the form of mixtapes. And these were real mixtapes—not mp3s, not CDs, actual mixtapes with the tapes inside. And these tapes were being funneled from the Bronx and from Harlem and they captured actual live performances from pioneer rappers—they called themselves rappers. I didn’t know what a rapper was until I got my first mixtape, and I was blown away by these pioneer performers that were creating this new life form as it evolved, and they had such glorious names. Names like “Grandmaster Flash and the Furious 5 MCs,” names like “Charlie Chase, Tony Tone and the Cold Crush Brothers,” these guys were like superheroes—these guys were like rap gods, pioneers, unapologetic and raw in their routines.
So imagine the first time I turn on the radio—WBLS—and the DJ announces that he’s about to play the first rap record. And I pop up and I listen and I hear the Sugar Hill Gang’s “Rapper’s Delight”—and I recognize it as rap but it sounds different. It sounds polished, it sounds commercial. And although I recognize it, I don’t necessarily feel that I’m a part of it, and I’m disappointed. And I ask myself—why is that whenever there’s a new phenomenon that’s organic and so personable to me, why is it that once it gets widely accepted, I don’t feel I’m part of that acceptance?
Years ago, I ran a small law firm, a boutique law firm the music industry. And I represented a lot of small clients that would grow to become major acts. And one of my clients at the time, his name was Sean Carter, who was also known as Jay-Z. So at the time Jay-Z wrote his name kind of differently, he had an accent between the Jay and Z, and an umlaut over the A, which was kind of weird.
But the thing that you noticed about Jay-Z even before the fame, and the fortune, and the recognition, is that this guy had an innate sense of influence. And I remember him walking into my office one day, and he had on this pair of Adidas, and I wasn’t a sneaker dude at the time, but he walks in, and these sneakers are screaming for my attention.
Now I don’t ask Jay-Z where he got those sneakers, because you don’t do that—you don’t ask someone where they got their fresh, because it’s an organic process. So, we’re conducting this meeting, Jay-Z finishes his business, he leaves, and no more than 2 minutes pass when my business partner runs in the office and says, “Reggie, did you see those sneakers that Jay Z had?”
So the very next day, I go to almost every sneaker store until I can find the same exact sneakers that Jay-Z wore. And the place where I found the sneakers was a spot located on Flatbush Ave. and State St, which was ironically right around the corner from where Jay-Z lived at the time, and where he famously wrote about in that song “Empire State of Mind.” So even then, Jay Z had this powerful sense of influence.
Years later, he’s a household name, and he’s recognized as a great artist around the world, but he’s also recognized for his power of influence. I mean, he drops a record in conjunction with major corporations like Samsung; he’s obviously influencing CNN; and he’s also influenced Fifth Avenue with a lot of clothing that’s in Barney’s at the moment—a place where I imagine at times Barney’s would have looked at someone like myself, or others like myself, and viewed us as outsiders. So once again this phenomenon of being on the inside, and then once it’s accepted, I’m on the outside looking in, not invited to the party.
You know, 2014, it seems like hip-hop is all over the place, but at the same time it’s not really acknowledged. So I’ll be sitting at home with my 6-year-old daughter and I’ll turn on PBS and I’ll see this cute kid’s show, with all these beautiful little white kids rapping to this cute rap song and this cute requisite, cutting and scratching; and I’ll turn the channel and I’ll see hip-hop hamsters dancing to a well-known hip-hop tune trying to sell me their product and I get it and I understand it, but I’m not part of that.
So, you know, for most of my life, hip-hop has been the soundtrack to how I view things. It’s helped change the lens in which I see everything: from high school, to attending Cornell University, to going to Georgetown Law, and as I studied constitutional law and contracts, my background music, my soundtrack, was hip-hop. And as I moved through life, going from a working class family, to working in corporate environment, to working in the music industry, to the literary world, it’s always shaped how I view things.
But at the same time, hip-hop and I kind of have this weird relationship with America. You know, we’re American—I’m American, hip-hop is American—we definitely have that stamp, “Made in America,” but at the same time, every now and again, when I get comfortable in my sense of my American-ness, something will happen to remind me that there’s also a sense of “otherness.”
And what I mean by that is incidents like Shawn Bell, Travyon Martin, things that will slap me in the face and say “You know what, you are American, but you are something else.” And I don’t want to credit that solely to race, but as a black man, that’s what resonates mostly with me. I’m an insider and I’m an outsider.
Like this incident that happened a couple of weeks ago. I was hanging out with some friends and we had some early-afternoon drinks, and I get a text from my lovely wife. She’s like, “Honey, I got a list of things for you to go shopping at Union Market to pick up.” So I have her shopping list, and I walk into Union Market, and I’m kind of like, a little tipsy, but I got to get my wife’s list correct. Cause I don’t want to go home and miss anything on that god damn list!
So I’m walking in and I’m picking up oregano, and gorgonzola, and garlic, and then it hits me: I’m the only black dude in the store. With a hoodie on. And all of a sudden I’m hit with a wave of paranoia, and I’m like, I don’t want to create a scene inadvertently: I don’t want to bump into anyway, I don’t want to knock anything off the shelf. So now I’m walking this fine tightrope of picking up everything on this list and not causing a scene, cause I’m paranoid as hell.
I’d like to report that I picked up everything successfully on that list, but it wasn’t an enjoyable experience! A couple of weeks ago, I’m sitting with a friend of mine, who’s in a very influential position of power—he programs a major urban radio station that services the tri-state area, and we’re talking about culture, and about music, and about light things, and in the midst of our conversation we start talking about race relations, and living in a post-racial America.
And, I guess he kind of senses something from me—maybe my ambivalence or this unease about being part of, but not part of—and he asks me out of the blue, “Are you an angry black man?” And I go, “No—I’m not an angry black man,” because an angry black man is the boogeyman, and you don’t ever want to be the angry black man. But I am an annoyed black man at this weird relationship of fitting in and not fitting in.
Now let me give you some background on my friend. I always perceived him as being very comfortable in his skin, and maybe that’s because he has the privilege of being a product of a biracial family. His mother’s Jewish, and his father’s African-American. So I see him walk through these positions of power, and he seems very comfortable. And as we’re talking, he starts arguing, he’s like, “Yo man, what’s your problem? You, and your family—when I look at you and your family—or when your fans or people that follow your work look at you and you family and how you move, we see a picture perfect snapshot of what the American family is today.”
And I’m like, “Yo you’re bugging.” So then he pulls out a trump card and he talks about my daughter. You don’t ever bring somebody’s daughter up in a conversation or in an argument. So, let me give you some background—my daughter is 6 years world, and she does some light modeling work, and last year she was selected to be on the cover of a prestigious magazine. She was selected to represent the class of 2025 on the cover of Time Magazine. And it doesn’t get more prestigious or American than that.
So he throws this in my face, my friend, and I’m like, “Okay.” And he says, “You gotta get out of your head in terms of how you internalize things.” And I’m thinking that, you know, I know that my experiences are real to me, these things have happened to me, I’ve seen things that made me feel like the other. But at the same time, I realize that he might be right, and that I might have to get out of my head, and start internalizing how other people view me—some other people view me.
Do I still feel like I’m on the outside? Of course, certainly, but I also realize that many of us in this room and across the nation, may feel at points like we’re on the outside, whatever our differences are. But at the same time I realize that, because of the work that I’ve put in, because of the work that many of my people have put in, we don’t necessarily need acceptance, because we already sit at the table that we’ve rightfully created.
And, I want to leave you with this point: if you’re ever very comfortable in an environment, and you see an individual or group of individuals that might initially strike you as not belonging, or as being the outsiders, you might want to reflect and think that maybe it’s you who’s the newcomer or who’s the outsider, occupying the space of the insider, and just be thankful that you’re benefitting from the foundation and the efforts that the insiders before you have created.
Edit news description to add:
- Historical context: how the event or text affects the world and history
- An explanation of the work's overall story (example: "Here, President Obama confirms the legality of drone strikes...")
- The work's impact on current issues