I used to love hip-hop. It used to be a huge part of who I was and how I saw the world. It hasn’t been that way in a long while. When I went to see Jay-Z and Kanye West on the Watch The Throne tour last year it was a bit like hooking up with an ex-girlfriend I hadn’t seen in a long time. It felt good and was tremendously enjoyable but it also felt weird and a little wrong. It was a reminder of who I used to be and what I used to care about instead of reflecting who I currently am. It served as a potent reminder of why I fell in love with hip-hop but also underlined the profound disconnect I feel from it as a 36-year-old. I felt melancholy, and as is often the case when you’re feeling bittersweet and conflicted and sad and happy all at the same time, my ennui had a soundtrack.

It’s hard to believe that it’s been 18 years since the release of Common’s “I Used To Love H.E.R.,” a landmark single that used the metaphor of a once-vibrant, then-stagnant romantic relationship to trace what the rapper saw as hip-hop’s unsteady evolution and devolution. When “I Used To Love H.E.R.” was released to massive critical acclaim and single-handedly established Common as an important artist, hip-hop was still a relatively young art form.


Where its cool uncles soul, funk, and jazz had been around long enough to grow wicked Methuselah-style beards, hip-hop was a scrawny up-and-comer barely able to cultivate patches of peach fuzz when Common simultaneously delivered one of rap’s greatest love songs and a trenchant critique of how the genre developed, where it went astray, and how it could win its soul back.

Hip-hop as a commercial entity was only 15 years old in 1994, but this is hip-hop we’re talking about, so they were 15 hard, eventful, and transformative years, years when the genre shifted and evolved dramatically and forever changed the face, sound and sensibility of pop music and pop culture. They were 15 years that shook the world, 15 years of growth and mutation and cross-pollination and icons and feuds, 15 years of spectacular growth and diversification.

That’s the irony of “I Used To Love H.E.R.”: Common was bemoaning that hip-hop had lost its way at a time when the genre was arguably at its zenith, in a year that saw the release of NasIllmatic and Notorious B.I.G.’s Ready To Die, as well as the first in a series of more or less universally brilliant and beloved RZA-produced Wu-Tang Clan solo albums, Method Man’s Tical. In the six-year span from 1988 to 1994, hip-hop seemed to evolve more than it has in the ensuing 18 years. Those were extraordinary times to be a hip-hop fan. How could you not fall in love with hip-hop during that sepia-toned golden age? Something exhilarating and revolutionary and groundbreaking was happening no matter what manner of hip-hop you were into.


In Houston, Scarface and his accomplices in Geto Boys were adding Shakespearean depth and profound psychological complexity to gangsta rap, accidentally inventing horrorcore, and crossing over with the haunting mainstream hit “Mind Playing Tricks On Me.” In Southern California, hip-hop was exploding across the spectrum. N.W.A. and then Ice Cube, Dr. Dre, MC Ren, and Eazy E were making incendiary, paradigm-shifting music that captured the zeitgeist and angrily demanded to be heard, while a weird-ass cousin of Ice Cube’s named Del The Funky Homosapien debuted with a funny and utterly unique album about taking the bus and some dude named Mister Dobalina.

In New York, a homeless teenager who called himself KRS-One went from posing with guns on album covers and helping evolve the nascent subgenre of gangsta rap to launching the Stop The Violence movement and anointing himself hip-hop’s conscience and ultimate arbiter of authenticity. Also in New York, Public Enemy and its brilliant production team The Bomb Squad were transforming noise and anger into transcendent art, and an eccentric genius named RZA was laying the groundwork for a musical revolution with a singular sensibility cobbled together from blaxploitation movies, kung-fu flicks, urban grime, and goosebump-inducing soul samples. De La Soul and Beastie Boys were elevating sampling to an art form with 3 Feet High And Rising and Paul’s Boutique, respectively. And De La Soul’s Native Tongues compatriots A Tribe Called Quest and Jungle Brothers seduced a nation of college students and white kids, and built a formidable legacy that endures to this day. Hip-hop was flowering across the spectrum: P.M. Dawn, Redman, Queen Latifah, Kid ’N Play, Basehead, X-Clan, 2 Live Crew, Big Daddy Kane, and Digable Planets might not have much in common, but they were all hip-hop. There was a strength and power in that.

I’ve been thinking a lot about “I Used To Love H.E.R.” lately. Like so much great art, the song is at once personal and universal. Common was telling the story of his own relationship with hip-hop, but he was simultaneously telling other people’s stories. These days, I feel like “I Used To Love H.E.R.” tells the story of my relationship with hip-hop as well. Like Common, I met and fell in love with hip-hop when I was still a child. As I grew up, the music grew and evolved with me. When I was 12 years old, I’d race home from school to watch Yo! MTV Raps and, more furtively, pay-per-video service The Box, which specialized in the kind of raunchy Miami Bass fare and T&A videos the more conservative likes of MTV shied away from. Back then, hip-hop was populated by characters so colorful they felt like sentient cartoon characters: droll storyteller Slick Rick, with his eye-patch and colorful yarns (his signature hit was even called “Children’s Story”); genial, beat-boxing clown Biz Markie of “Pickin’ Boogers” and “The Vapors” fame; tongue-in-cheek wisenheimers Beastie Boys, the nascent genre’s answer to the Bowery Boys; the literally outsized characters in Fat Boys; the effortlessly cool Run-DMC; and my favorite at the time, Fresh Prince And DJ Jazzy Jeff.


“Rap is not pop if you call it that then stop” famously insisted Q-Tip on A Tribe Called Quest’s “Check The Rhime” in response to MC Hammer’s flagrant crossover moves and massive mainstream success. But my personal experience with hip-hop told me otherwise. The rappers I loved and gravitated toward were making pop music whether they wanted to admit it or not. Hell, A Tribe Called Quest trafficked in the infectious hooks and sleek, shiny surfaces of superior pop music, even if it wrapped them up in trendy Afrocentric garb. There was no shame in making pop music everyone could enjoy. In the right context, rappers making pop music could even feel revolutionary, like when Run-DMC reluctantly yielded to the wishes of producer Rick Rubin and collaborated with Aerosmith on “Walk This Way,” a collaboration that exposed hip-hop to a whole new audience and finished the job Run-DMC’s early videos started in making hip-hop safe for the influential, star-making likes of MTV.

My first exposure to hip-hop came when I was about 8 years old and a cousin asked my dad if he’d heard a song called “Rapper’s Delight,” then already a few years old. In 1979, Sugar Hill Gang took the nascent genre from the streets and block parties of New York to a mainstream national audience through artful theft of other rappers’ rhymes and relentless pandering. Rap would go on to become the sound and aesthetic of incendiary black rage, but it was introduced to radio listeners through an aggregation of smiling black men enthusing, “Guess what America, we love you!” over a peppy disco beat purloined from Chic’s “Good Times.” My dad responded that he hadn’t and the cousin confidently replied, “Oh, you should. It’s hilarious! It’s got lyrics like ‘hotel / motel / Holiday Inn / If your girl starts acting up / then you take her friend!”

To my pre-pubescent ears, that sounded awfully silly but also exciting and a little naughty. In my cousin’s mind and the minds of plenty others, hip-hop was essentially a fun but eminently disposable fad, no different than breakdancing or Cabbage Patch dolls. It was good for a few guilty laughs and nothing more. Who could possibly take it seriously with lyrics like that? Yet hip-hop did not come and go, as so many expected it to. What initially appeared to be a blip on the pop-culture radar became a cultural force that transformed our country and our culture en route to conquering the world.


When I was a child, hip-hop seemed made for me. It was big and bold and cartoonish, Day-Glo and larger than life. When grade school gave way to the angst of middle school and then the gauntlet of emotional agony that is freshman year of high school, I gravitated toward music that expressed the tumult of conflicting emotions raging inside of me. On one side, N.W.A.’s Straight Outta Compton expressed the ferocious nihilism and rage I felt far more powerfully and compellingly than I ever could. It spoke to every angst-ridden adolescent’s desire to fuck the world or set it on fire, possibly at the same time. At a time when I felt powerless and vulnerable, hip-hop made me feel powerful and bulletproof. It spoke to the fantasies of power and virility shared by every misfit kid who grew up thinking the world has no place for him, and it did so in language that was at once coded and intoxicatingly blunt.

If gangsta rap spoke to my inner Incredible Hulk, the rampaging creature of id and ego who wanted to smash the world into a million little pieces, the bohemian chill-out music of Native Tongues, PM Dawn, and Basehead spoke to my inner Bruce Banner—the thoughtful, reflective and adult person I hoped to become if I could make it through high school with my sanity relatively intact. Though I was and remain painfully white, I responded powerfully to the Afrocentrism, rage, and Black Nationalism of golden age hip-hop. I spent my teenage years in a group home for emotionally disturbed adolescents on the North Side of Chicago and pro-black hip-hop told me that there was nothing wrong with being different. At an impressionable age, I was being told by this outsider music that very things society said should fill me with shame were actually sources of pride.

Throughout college and my early 20s, hip-hop was both the soundtrack of my life and the art form that got me into writing professionally, albeit for $5 a review for the Madison Area Technical College newspaper Slant. In good and bad ways, hip-hop shaped and molded me. Its poisonous gender politics and deeply ingrained misogyny affected me more than I’d like to admit. With hip-hop, I took the good with the bad. It was all part of the grand gestalt. When I felt invisible as a college freshman, having 2Pac in my headphones hollering about thug life and being a self-made millionaire made me walk a little taller and feel a little bolder.


When I started writing about music for The A.V. Club back in 1998, beginning with the soundtrack to Bulworth, hip-hop gave me a niche. By the late ’90s, hip-hop was big business. There were thousands eating off the art form. I was one of them. Throughout my adolescence and early adulthood, hip-hop was my Giving Tree: It gave and gave and never asked for anything in return.

Then something changed within me, or the music that I loved, I’m still not entirely sure which. If I could pinpoint the start of my growing disillusionment with hip-hop to one artist and one cultural moment, it would have to be the seemingly inextricable rise of 50 Cent in 2003 with “In Da Club” and Get Rich Or Die Tryin’. I just didn’t fucking get it. I felt fatally out of step with the rest of the world. To the rest of the world, “In Da Club” was irresistible; to me it was a joyless, sneering dirge and its creator a soulless, calculating asshole.

At the risk of generalizing, before everyone hated 50 Cent, everyone loved 50 Cent. The release of his 2003 Shady/Aftermath debut was a cultural event. They damn near closed down schools and businesses and declared it a national holiday. I’ve come to appreciate 50 in hindsight, but at the time, his ascent underlined my growing estrangement from hip-hop. To paraphrase Matthew McConaughey’s famous line from Dazed & Confused, as I got older, hip-hop stayed the same age. Time marches on, yet hip-hop, like pop, is forever 21, even if it still has plenty of fans in their 30s and 40s who remain actively engaged in the music and culture in a way I haven’t. I didn’t outgrow hip-hop necessarily, but the older I got, the more preposterous and unsatisfying its adolescent fantasies of omnipotence and ultimate power became.


Hip-hop’s eternal adolescence is central to its enduring popularity and appeal—like a vampire, it feasts on the blood of the young in its bid to never grow old—but like everyone, I long for music that speaks to my life and my struggles. Everyone wants to see themselves reflected in the art they consume, but even middle-aged rappers remain fixated on party and bullshit while their continually aging audience wrestles with mortgages, marriage, kids, back pain, 401Ks, retirement plans, and the like. I would love it if there were a hip-hop equivalent to Older Than My Old Man Now, Loudon Wainwright III’s masterful concept album about death and decay, but I can’t see that happening any time soon. Rappers who do write truthfully about what Notorious B.I.G. called the everyday struggle, like the blissfully grown-ass Phonte, formerly of Little Brother, remain the exception that proves the rule.

Like Common, I’m tempted to put much of the blame for my growing estrangement with hip-hop on gangsta rap. A subgenre that once felt extreme, revolutionary, and liberating grew ossified, calculated, and grotesque early in its development. It lost whatever connection it had to gritty, unvarnished reality and became a realm of sociopathic make-believe, a blood-soaked fantasy land where outsized caricatures of aggressive masculinity could sell drugs, take drugs, treat women like disposable sex objects, kill motherfuckers, and never have to take responsibility for their actions. When you’re 14 and quivering with incoherent rage, that’s incredibly exciting. But when you’re 36 and thinking about what kind of a world you’d like your children to inhabit, that’s sad and more than a little pathetic. Furthermore, when hip-hop became big business it lost much of its soul and eclecticism. Labels began chasing the next 2Pac or the next Biggie or the next Eminem or the next Neptunes instead of embracing the variety and inclusiveness that characterized hip-hop during its golden age. What’s more, hip-hop itself started acting as if its glory days were behind it.

Hip-hop’s reverence for the past, always one of its most endearing qualities, devolved into an unwillingness to move forward. It’s been decades since A Tribe Called Quest and De La Soul forever expanded the boundaries and parameters of hip-hop, yet in some ways hip-hop has never evolved beyond the innovations people like Prince Paul and Q-Tip introduced when they weren’t even old enough to drink. Just about every act I’ve fallen in love with over the past 15 years has had its roots in Native Tongues, from Little Brother to Black Star to Madlib to MF Doom (who was actually part of Native Tongues affiliate KMD) to Kanye West, who is an utter original in so many ways, but whose production style is half RZA, half Pete Rock.


Hip-hop has not failed me. If anything, I have failed it. All relationships require work or they will atrophy and die. I stopped doing the hard work of being a good citizen of hip-hop nation years ago. I stopped aggressively seeking out new artists. I stopped going to shows. I retreated into the comforting cocoon of the familiar. I don’t want to blame hip-hop for the estrangement I now feel from it. I have changed as much as the music has. We’ve grown apart due to differences that seem increasingly irreconcilable the older I become. While it feels to me that the music hasn’t evolved since the mid-’90s, it certainly has changed. Hip-hop has not remained stagnant. New movements have come and gone. Since hip-hop’s golden age we’ve seen the emergence of such subgenres as grime, crunk, reggaeton, hyphy, and N.O bounce, but none of these movements resonated with me at all, let alone affected me as profoundly as Native Tongues did. If hip-hop doesn’t rattle my soul the way it used to, that might be because my taste in hip-hop stopped evolving. Times change and people change: I doubt DJ Jazzy Jeff and The Fresh Prince’s He’s The DJ, I’m The Rapper would mean as much to me if I encountered it as a 36-year-old rather than as an 11-year-old.

With Hip-Hop And You Do Stop, I’ll explore the trajectory of my long, complicated love affair with hip-hop, from the giddy burst of exhilaration and intoxication I experienced listening to Run-DMC and D.J. Jazzy Jeff And The Fresh Prince to the increasing distance I felt from the genre as the ’90s morphed unmistakably into a new millennium. I do not want this column to become the critical equivalent of a cranky old man yelling at contemporary hip-hop to get the hell off his lawn and turn down that crazy, disrespectful music while they’re at it. The hip-hop of today isn’t bad; it’s just different. If hip-hop doesn’t speak to me these days the way it used to, that might be because I’m old and out of touch and the modern music that leaves me cold isn’t intended for men nostalgic for the heyday of Pete Rock & CL Smooth. Like a lot of hip-hop since the genre’s birth, it’s fundamentally dance music, and I haven’t pop-locked or dazzled folks with an expertly executed helicopter in many a decade (or ever, if you want to be brutally honest).

Good hip-hop is still being made. I just haven’t been as diligent about seeking it out as I should be. Instead of seeking out the music of the future, I cling to my cherished memories of hip hop’s past, which I have thoughtfully tinted sepia-toned and decided to revisit for this project. Each new entry in the series will follow a year in hip-hop’s evolution and de-evolution, beginning with 1988, the first year of the genre’s golden age and the year I procured my first hip-hop cassette, DJ Jazzy Jeff and The Fresh Prince’s He’s The DJ, I’m The Rapper, and closing with 2000. Decades are tidy chronologically but messy thematically, so for me, hip-hop’s ’90s heyday began in 1988 and lingered on until 2000 with the release of such ’90s-style classics as Quasimoto’s The Unseen, Reflection Eternal’s Train Of Thought, Slum Village’s Fantastic Vol. 2, Ghostface Killah’s Supreme Clientele, and others. Hip-hop had such a spectacular ’90s that it had enough juice left over for an extra year, a bonus track as it were.


What follows is a deeply personal, idiosyncratic account of hip-hop’s golden age and long, slow decline. It does not aim to be definitive or exhaustive. I am not telling the whole story of rap. That would be impossible. I’m cataloguing my personal experience of hip-hop. My taste is not orthodox. I’m not even sure my taste is particularly good. My hip-hop knowledge is full of blind spots and weird, borderline unfathomable preferences. I’ve listened to pop-rap goofballs Nice & Smooth far more than the eminently more respectable Public Enemy. J-Zone has historically meant more to me than the godlike Rakim. I’m warning you now: Your favorite artist will be slighted, ignored, or given short shrift. So I apologize in advance for that.

So welcome aboard. We’re about to travel back to the source, to a time when hip-hop radiated all the promise in the world. So sit back and enjoy the ride. I will do everything in my power to make it worth your time.

Next time on Hip-Hop And You Do Stop: A golden age begins as DJ Jazzy Jeff & The Fresh Prince and N.W.A. make hip-hop seem as American as apple pie and as terrifying as a Molotov cocktail in your mailbox, respectively.