So Far to Go: Post-Racial Pop in the Age of Obama

by Dax-Devlon Ross

(It’s been two years since my last post on this blog. I’m glad to be back! Enjoy!)

So Far to Go:

Post-Racial Pop in the Age of Obama


“[I]n order to understand the outlier I think you have to look around them—at their culture and community and family and generation. We’ve been looking at tall trees, and I think we should have been looking at the forest.”

Malcolm Gladwell, author of Outliers: The Story of Success

My most recently published book, The Nightmare and The Dream, is, in a nutshell, a comparative study of rival African-American ideologies and the icons who embodied them. Obviously, I like to think it’s about so much more than that, but really that’s what it is. Nightmare was the culmination of an idea that I pursued as far as my mind would allow it to go.  I was fascinated by the similar stories of these men’s lives; I still am. Which is why 23 year-old hip-hop sensation Drake (along the range of feelings his crossover success has provoked in people) is so interesting to me. I need to understand why The New York Times has boldly anointed him the “new face of hip hop,” corporate America is ardently pursuing his services and Hollywood is chomping at the bit. I think he’s trying to understand why. I think we are all trying to understand why.

I have a theory: Drake is pop culture’s answer to the Age of Obama.

Hang on.

Hear me out.

Who’d heard of Drake in 2008? I certainly hadn’t and I like to think I stay up on my pop culture. Even when I began to hear his music in 2009 I didn’t pay much attention. He sounded like someone biting Kanye’s style. But, as the Age of Obama has settled in over the last year, he’s stuck. Now he’s considered, for the time being at least, a fixture.

Maybe we should take a step back before we go any further. What exactly does it mean to be living in the Age of Obama anyway? Meaning, does it have a look? A feel? Well, in the nearly two years since the election one controversial term has materialized in the American discourse: post racial. As a society we’ve struggled to come to a consensus about the meaning of the term (let alone its merit), but we seem to agree it has something to do with the idea of Americans transcending their fixation on race as a criterion for assessment of any kind.

That being said, some of the characteristics I would expect to see reflected in a post-racial society are a broader acceptance of and openness to difference, improved cross-racial alliances and an end to discriminatory practices against people on the basis of race.  Anyone who’s seen recent employment, housing, healthcare, education, and incarceration data would agree that we’ve yet to reach these lofty ideals as a society; however that hasn’t stopped the pop-culture industry from spending the last couple of years bulldozing us into the post-racial era. Whether it’s the perceived wave of celebrities adopting black babies, slick ad campaigns bending over backwards to celebrate cross-racial bonding or Hollywood hits glossing over racially sensitive subtexts and storylines (The Blindside and Avatar), we’ve been inundated with post-racial innuendo that more often than not blur the already fuzzy line between race and class. In the end we’re left to sift through the morass and figure out where we really are on our own.

Nightmare’s subtitle is Nas, Jay-Z and the History of Conflict in African-American Culture. As one perceptive reviewer put it, the book’s aim is to position hip hop (both the music and the culture) within a larger historical framework in order to decipher the coded messages it’s trying to tell us about ourselves. In it I argue that Jay-Z remixed the conventional Horatio Alger myth in the ’90s and ’00s. He told us the story of his transformation from the ultimate outsider (drug dealer) to the ultimate insider (mainstream darling/mogul) over and over again and we responded to it, over and over again. Why? Because our belief in that upward mobility hustle is imbedded in our DNA. And then, to his credit, Jay-Z has an uncanny feel for the moment and sense of timing. “Hard Knock Life” told the tale of the hustler’s come up, “Big Pimpin” captured the late ‘90s stock market frenzy, “Heart of the City” was the balm that soothed our post-9/11 angst and “Empire State” signaled the resilience of the great American city.

The book is my way of legitimizing hip hop to myself and anyone else who cares, of saying just because it’s music doesn’t mean it’s just music. I believe, firmly believe, that art tells us who we are,  where we are up to, what we believe, what we care about—all of that. This is art’s most important function, why so much of the most important art goes unnoticed for generations. We don’t want to see ourselves.

Thing is, we can never avoid ourselves, just the parts we don’t want to see. It’s a helluva condition. The artist always looks, though. She can’t afford not to. She stares into her soul and extracts. After spending years  studying his work, my sense is that Jay-Z has remained relevant for almost fifteen years because he’s always looked inside himself and revealed what’s there given, even when that self wasn’t pretty.


When he entered our collective consciousness at the Democratic National Convention in 2004, Barack Obama birthed a new political and social paradigm. If Bill Clinton authored the quintessential pull-yourself-up-by-your-bootstraps story for Generation X, then Obama scripted the post-millennial outsider narrative for Generation Y. He was the man (or woman) who, instead of overcoming his background to claw his way to the top on sheer will and talent, made his unique and complex American odyssey his greatest political asset. We were as fascinated by his spirited rhetoric as we were blindsided by his sudden rise. Quite simply, we’d never seen anything like him before. As a nation our natural initial reaction was skepticism. Where did he come from? What did he really stand for? Whose decision was it to place him in a position of prominence? For a time we kept him at arm’s length. His skeptics – and there were many, myself included – distrusted him. He wasn’t really a brother. He didn’t really know the black experience. But then we went out and bought his book – a book that had been practically ignored for nine years – and became believers. We discovered someone who had journeyed deep within himself to find himself. We discovered someone not unlike ourselves. An outsider. A child of a single parent. A young man bravely searching for who he was and sharing what he had discovered with the world. We connected with his story. All of us. In some way, we all found an entry point, a way to relate to him. Slowly (then rapidly because of the internet) we began to believe in his truth. Under the umbrella of “change” a movement began.

I’ll never forget the conversations I had with friends in the days after the election. We felt proud to be Americans, some of us for the first time in our lives. We felt a weight lift off our shoulders. We also wondered what the generation behind us was experiencing. How would living in the Age of Obama alter their lives? What new possibilities would his existence create for them? What new ways of being would be open to them? At 23, Drake is a bona fide member of Generation Y.

Obama’s campaign for president obliterated the notion of a single black experience and shined a light on the diverse experiences within the black experience. He opened up people – even black people – to stories that had  previously been relegated to the social and artistic margins because they didn’t fit the dominant narrative we’ve become accustomed to telling and hearing about black Americans. In this sense, Drake’s “overnight” celebrity should be read, in part, as the product of Obama’s achievements. Obama made outsiders cool.

But that’s just a starting point. Their connections run much, much deeper.

Let’s start with the obvious. They both had black fathers and white mothers. Now let’s take it one step further. According to all accounts, neither of their fathers played a consistent role in their lives. It was their mothers, remarkable, progressive-minded women, who raised them and instilled in them the values that they continue to measure themselves by.

“She was the dominant figure in my formative years … The values she taught me continue to be my touchstone when it comes to how I go about the world of politics.”

Barack Obama

Everything good in life I get from my mom … the desire to be intelligent, kind, caring…”


Furthermore, they both grew up outside of the mainstream black American context. Obama spent his childhood in Hawaii and Thailand. Drake spent his in Canada. They both attended predominately white schools and were raised in predominately white surroundings. Despite growing up outsiders, they both elected to join a black community and adopt its customs (basketball, the black church, black music, etc.). This is a crucial point because Barack Obama’s authenticity as a black man in the eyes of black people was built upon the choices he made: to work as an activist in Chicago, to marry a black woman, to join a black church. Similarly, Drake’s initial stamp of authenticity and credibility in the hip-hop community came from his relationship to Lil Wayne and Wayne’s outlaw reputation. This isn’t to say either of them didn’t have talent or that part of what makes them compelling figures is their complexity, their malleability and their charisma; it’s to say credibility and authenticity were necessary ingredients in their rise. Given the status of blacks in America (both perceived and real), the significance of this decision cannot be understated. They may not have chosen to be biracial, but they chose to identify black; moreover, their mothers supported them in this choice.


Now that we’ve established some fundamental similarities, think back to 2008 for a moment.  What made the Obama candidacy different than presidential candidacies that preceded it? You could say Obama’s refreshingly genuine spirit. Or  his vision for a new America. Or his campaign’s mastery of internet campaigning. What I remember most is this incredibly organic, populist aura surrounding the campaign, this feeling that his candidacy was not being manufactured by the same, tired-ass powerful insiders, but by millions of regular people donating whatever we could (time, money, etc) to aid the party-crashing underdog without the conventional political pedigree. Along the way Obama became a symbol for Americans who felt dissed, forgotten, overlooked, underestimated, unrepresented—anyone who had beef with the America that had emerged from rubble of 9/11. His campaign in turn came to represent an all-encompassing grassroots movement against the establishment. His critics and detractors never seemed to grasp this. They harped on his lack of experience (“He hasn’t proven anything yet.”), belittled him as a glorified speech maker (“Good speeches don’t make a good president.”), questioned his loyalty, his identity, his character. They never, ever grasped what people were really responded to: his story. He was the new America, the new global citizen.

Which is why when I heard myself joining the Drake-Hate campaign for the same reasons and without giving him a serious chance, I had to stop myself. I thought back to the Obama campaign. I thought about Andrew Young, Jesse Jackson and Al Sharpton—the old guard. I thought about their reluctance to support him, their criticism, their petty acts of sabotage. I thought about the complex emotions his success stirred in so many people. Resentment. Joy. Disbelief. I remembered trying to read Jesse’s tears in Grant Park the night of the election. Is he happy? Is he jealous? Is he hurt?

Then I had an honest moment with myself. “Dax, are you the one who’s out of touch this go round?  Have you become that guy who hates on anything popular simply because it’s popular? Who automatically equates mainstream popularity with superficiality?”

I copped Thank Me Later and carried it on a Friday night road trip to Philly. At that point I’d only heard the radio hits.  They were catchy. I checked my baggage at the door and entered the listening experience with an open ear. By the time I returned to Jersey the next morning I was a believer. By Monday I owned the So Far Gone mixtape along with the Cookin Soul/Don Cannon remix, Thank Us Later. They’ve all been on heavy rotation since.

If I had to put a label on it, I’d say Drake’s greatest asset as an artist right now is his earnestness. Because he’s earnest, he’s willing to experiment. Because he’s willing to experiment (with his voice, his flow, his feelings, etc.), his music feels fully realized. He  may not (yet) be the witty wordsmith that Jay-Z is or the vivid story teller that BIG was, but his lyrics are shrewdly sketched scenes of the topsy-turvy life he’s leading. On “The Resistance,” a hauntingly anguished confession, he raps, “I heard they just moved my grandmother to a nursing home/ And I be acting like I don’t know how to work a phone/ But hit redial you see that I just called/ Some chick I met at the mall/ that I barley know at all …”) Likewise, he may not be a poet-polemicist like Nas or emote obsessively like 2Pac, but throughout the album he skillfully juggles sobering clarity (“So they tell me that they love me, I know better than that, it’s just game/ It’s just what comes with the fame, and I’m ready for that …”) and tormented ambiguity (“I couldn’t tell you where the my f-ck head is/  I’m holding on by a thread/ It’s like I’m high right now.…”).  At times he’s audacious (“It’s about time you admit it, who you kiddin’, man?/ Man, nobody’s never done it like I did it … ). At times he’s anxious (What am I afraid of?/ This is what dreams are supposed to be made of.…) He’s as obsessed with remaining true (“Promise to always give you me, the real me”) as he is with the vagaries of the fast life (I’ve been up for four days/ Getting money both ways/ Dirty and clean, I could use a glass of cold spades/ Rolexes, chauffeurs, and low fades …”), as hurt by lost opportunities at love (“Man the good girls went silent on me/ They got a boyfriend or left for college on me …”)  as he is frank about his capacity to make anything work (“I think I have a chance at love but knowing me I miss it/ ‘Cause me dedicating my time just isn’t realistic … ”).

The challenge of any artist is to get out of the way and be the vessel for creativity. As long as an artist’s ego is in charge, the art remains rigid. Drake seems to already get this. Thank Me Later aims to paint a complete picture of a young man navigating the brand new terrain of fame, and comes as close to succeeding as anything I’ve heard. More importantly perhaps, his generation is listening and responding favorably.


“When outliers become outliers it is not just because of their own efforts. It’s because of the contributions of lots of different people and lots of different circumstances…”

Malcolm Gladwell

In the midst of writing this piece I had a conversation about Better Than Good Enough, the MTV documentary featuring Drake, with the hip-hop artist Fedel. We both agreed that the doc was fascinating and well done. Toward the end of our conversation I asked him whether Drake’s success would have been possible six years ago. “No way,” was his response. Drake either wouldn’t have been accepted by the mainstream or the music industry wouldn’t have known how to market him. 50 Cent owned the rap charts from 2003 to 2006. Then came Ludacris, T.I, The Game, and of course Lil Wayne—all emphatically hardcore braggadocio rappers cut from hip-hop’s ultra-conformist cloth. OutKast’s eclectic Speakerboxxx/The Love Below crept in the back door and won the Grammy for Album of the Year in ’04, but it was also the duo’s fifth album in nine years, meaning they’d already created a major body of work before breaking through to the mainstream. So if the question is who paved the way for Drake’s breakthrough, the answer has to be Kanye West.

West’s first two albums (College Dropout and Late Registration) are fairly conventional rap recordings. They are very good to great but don’t break new ground or challenge the genre’s conventions. Not until 2007’s Graduation and 2008’s auto-tuned, synthed-popped 808’s and Heartbreaks did the experimental Kanye first surface then soar. For all of his egomaniacal ‘I am the voice of this generation’ self-praise, Kanye has to be credited with channeling the atmosphere of “change” through his music. Like Andre 3000’s brazen defiance of hip-hop’s aesthetic conventions in the late 90s (and, I might add, Arrested Development and PM Dawn years before), West’s desire to push hip hop as far away from ring-tone rap (epitomized by Souljah Boy) as humanly possible a provoked derision then praise, and, ultimately, progeny. Simply put, Kanye’s influence on Drake is undeniable. Stylistically, Drake’s cadence and tone often echoes Kanye’s. Similarly, West’s penchant for periodic confessions (“I spent 400 bucks on this/ Just to be like nigga you ain’t up on this …”) crawls through every crevice of Drake’s initial offering  (“Cause all this shit is new to me, I’m/ Still learning to behave/ And still spending every dollar they/ Encourage me to save …”). To his credit, Drake clearly isn’t as obnoxiously bombastic as Kanye.

However you might have felt about 808s and Heartbreaks as art, its melancholic, meditative motifs opened a mainstream lane for Drake’s sound in the same way Obama’s outsider narrative opened a mainstream lane for Drake to confidently represent an authentic identity that has up to now been kept at arm’s length by the hip-hop cognisati. (Case in point: in 2000 Jay-Z was touring with Beanie Sigel and Memphis Bleek; in 2005 he was guiding Kanye West’s career; in 2010 he’s sharing mikes with Drake. Not only does this shift reflect the changing face of hip hop and what “keeping it real” has evolved to mean, it explains why Jay-Z has remained relevant.) What’s really interesting, though, is that these two phenomena – along with the digitization of music and file sharing – were operating on parallel tracks. His talent, hard work and desire are unmistakably his own, but his explosive commercial appeal represents the convergence of these phenomena.


Obama entered the national scene telling a story we could all relate to and that no one could deny. He was eloquent and optimistic. He was a dreamer. But the shadow story – what Obama wasn’t – was equally important. He wasn’t Al Sharpton or Jesse Jackson. Everything from his biography to his ideology to his pedigree pointed toward the arrival of a new black man and the departure of his stubborn predecessors. Ultimately it was that difference – the ability to transcend race – that mattered to voters. Make no mistake, corporate America was taking notes. Before Obama, corporate America couldn’t even figure out how to market black television shows to a mainstream audience. Barack Obama’s campaign literally taught corporate America the keys to marketing black people to the mainstream.

  • He or she must be considered authentic by black people but cannot inspire fear in white people
  • He or she must speak Standard English but be able to switch to contemporary hip jargon on cue
  • He or she must look black but not too threatening
  • He or she must not aggressively challenge status quo but cannot appear too meek to black Americans
  • An exotic back story is a plus
  • Multiraciality is a major plus

In Better Than Good Enough Drake comes across charismatic, compelling, humble, happy, hungry, wise beyond years and refreshingly articulate (yes, I said it). You watch him and you think some of the same things you thought when you watched Obama on the campaign trail: this is someone who will go far in America if he plays his cards correctly.

This isn’t a coincidence. Like Obama, Drake is an outlier. In our race-fatigued nation this is an advantage. “The fact that he has a background that differs from your prototypical rap artist,” his business manager boasted to The New York Times, “corporate America, they’re attracted to that.” I don’t have anything against an artist getting paid for his talents; nothing at all. What’s problematic is the message implied in the shadow story. Let’s switch gears for a moment. Just a moment. On and off the hardwood Lebron James has symbolized the post- Allen Iverson generation. Iverson was the cagey, thugged-out, anti-establishment anti-hero; James’ corporate image is neat, agreeable, and pro-establishment. Both are valid expressions of black youth culture, but both cannot exist in mainstream America’s psyche.

This is the continuing failure of the purported post-racial America.

Competing and even conflicting notions of blackness are still pitted against one another. One is always the good black; one is always the bad black. One has to be denigrated so the other can be celebrated. Neither can simply be. Similarly, the shadow story underlying Drake’s emerging corporate image – that he’s not 50 Cent, The Game, Kanye West, Lil Wayne, T.I. or any other rapper for that matter – is self-evident. But it is also reductive, dismissive of the reasons for their discontent and, ultimately, insensitive to the experiences that both spawned and carried rap music to the top in the first place. Rap was and still is music that tells the stories people may not want to hear but need to hear. Even at its ugliest it’s merely a reflection of our society.

In the final analysis, Drake’s crossover appeal tells me we’re still in deep state of denial about race in America. Far from showing me how much things have changed in the Age of Obama, corporate America’s fascination with his multiracial background speaks to our continuing obsession with race. In fact, all his mainstream acceptance does is allow Americans to feel post racial, enlightened, tolerant, etc., even though this assessment stems from his facility with middle-class signifiers.  In other words, as long as we as a society are charmed by an intelligent black kid who can speak well we’re implicitly saying we still don’t believe most black kids are intelligent and can speak well. Otherwise, what’s the big deal?

Back in June reported a story on Drake’s visit with Lil Wayne at Rikers Island. During the meeting the imprisoned rapper called his protégé the “ultimate artist” because he didn’t have the tattoos and didn’t cause trouble. “People like you,” a somber Wayne reportedly said. I thought about Jeremiah Wright when I read that line. It was a painful reminder of the price Obama had to pay for his success. The American public demanded that he divide himself from Wright to prove his loyalty, which he did. And when Wright spoke out against the media’s attempt to malign his legacy, the American public required Obama to bury him, which he did, albeit reluctantly. One has to wonder if Wayne already sees the writing on the wall.