DD Osama’s homecoming was a vision of rap’s future

A few years ago, during the brief periods of their lives they were into it, I took my son and daughter to a Paw Patrol live performance in MSG, a clear and in my mind, borderline illegal extortion scheme intended to milk parents with children susceptible to YT Kids ads of their hard earned savings. Before last Friday night, that had been the youngest audience I was ever a part of. 

But on May 12th, what felt like the first evening of early Summer, that spectacle had its title snatched by DD Osama’s New York city debut at the former Highline Ballroom, rechristened as Racket, on W. 16th street, in the shadow of the desiccated husk of an elevated freight line running along a once industrial stretch of the island’s Western shore. The ostensible drill show was a Lord of the Flies style society, overrun by very young children, adolescents in need of a chaperone to gain entry, and their young caretakers, who were also fans of the rapper. It was a cross between a middle school dance and the hellscape daycare from Toy Story 3 Woody and Buzz get trapped in. The featured cocktail was called “Throw”, named after a Lil Mabu and DD hit (which has racked 17 million hits in four months), a groundbreaking mix of Sprite with a splash of grenadine, for five dollars a pop.  The show—both in terms of DD’s performance and in mixing in with a crowd unlike any I’d been a part of in over 25 years—remapped my understanding of the drill artist and his medium.

If you’re not exactly familiar with the name DD Osama, but it rings oddly familiar, it likely means you’re over the age of 21, and read about the tragic murder of his little brother Ethan Reyes, or Notti Osama last summer in what was believed to be a result of gang conflict. The fatal stabbing of a 14 year old would be catastrophic anywhere on Earth, but the particular level of not just apathy, but celebration of his death churned the stomachs of even the most seasoned old heads. The “Notti Bop,” by Kyle Richh, briefly became a viral sensation, and featured elementary school aged children tricking cops, teachers, their parents, and their baby siblings into doing a dance that specifically mimed Notti’s murder. 

In the wake of the tragedy, DD’s career took off. The path in front of him, from survivor to full blown rap star, is one of the most challenging in rap’s modern era. DD will never be able to run from or uncouple himself from his legacy of grief, and wouldn’t want to. He has over a million followers on Instagram, and over 150,000 on Tiktok. It would be hard to imagine garnering that level of attention for a drill rapper in his first year with DD’s limited musical output, and it would be difficult to argue some of his popularity is tied to that infamous tragedy. But it would be equally dishonest to dismiss DD’s talent in his own right. As a young artist, DD displays a dynamism and versatility that is rare in his microgenre. He is comfortable in the aggro, screamy, quasi hardcore register of New York drill and dabbles in it often. But just as often, he drops into a subdued, conversational, musical delivery familiar to any 90s New York fan, and he can also sing. 

With this diverse skillset, DD and his label Alamo have been remarkably successful in beginning the work of establishing DD as an artist in his own right. He has achieved a Bieber-like level of celebrity among the fervent elementary, middle school and high school aged followers of  New York drill’s insular scene (particularly young women), sporadically dropping singles and low-budget, paint-by-number YouTube videos, collaborating with similarly kind-of-famous drill rappers and racking up millions of views. He has begun seeing out of town success, selling out venues as far flung as Chicago and LA. But it appears he is just beginning to whet his ambition.

The first real step in the quest for hegemonic pop dominance comes in the form of Here 2 Stay, released Friday, the reason for the show. It’s DD’s debut “project” (I’ve been told in strong terms not to refer to it as an album), which I found somewhat shockingly experimental and diverse, the work of an artist begging to tease out the parameters of who he is and what he’s capable of. It features songs that aren’t drill at all, conventional pop rap that could play across the dial, featuring light bars and hooks in his pleasant singing voice, songs that could live comfortably alongside 90s Trackmasters’ rap/R&B hybrids. 

When the project does feature the sample drill beats that have created the first distinct and nationally notable sonic scene in New York in decades, they aren’t the ADHD addled, fat, red meat, instantly recognizable samples the genre has hung its hat on (aside from what could be DD’s biggest hit, “40s N 9s” that samples Ne-Yo’s “So Sick”). The intention appears to be to center DD. It’s a star vehicle, and an often successful one. Here 2 Stay also leans into the loss of Notti, dedicating dozens of bars and several entire songs to DD’s fallen brother and inspiration. The songs are deeply vulnerable and raw, and sound very much like the poetry of a 16 year old kid attempting to begin what will be an excruciating, lifelong process of coming to grips with and articulating unfathomable anguish.

Which brings us to Friday night. Several months ago I had pursued a more traditional profile of DD for another outlet, never getting past Alamo’s front door for reasons I am highly sympathetic to. They are, understandably, extremely protective of their young artist, less than a year removed from an event that would shatter most people, and are dictating terms around access to him to prevent vultures like me from doing potential damage to his psyche and his burgeoning career. At the time, it was explained to me that if I wanted to shadow DD for a show, it would have to be out of state, because hosting a show for him in New York presented a number of risks to his safety. 

My first impression that the show wouldn’t be the tension packed tinder box that was then feared came the moment I hit the corner off 10th Ave. The scent of bodega purchased Delta THC variants was pungent, nothing special for a rap show, but what was novel was the makeup of the line, stretching past the Western Beef awning next store, nearly down to 9th. When I passed by around 7:00, there was a stunning number of kids below 10 years old, because the show was all ages, so long as the child was accompanied by a guardian. It brought me back to my beginnings as a live rap show attendee at 13, when I was still limited by parental advisory stickers. When the events were seen as illicit, and heavily regulated in the city’s confines. Suddenly, I found myself hip to shoulder with rap’s great grandchildren, in a Chelsea sweatbox for a concert, treating the event like a sandbox, alongside their parents I was older than. 

DD took the stage and immediately separated himself from the rest of his talented and presumably more experienced co-stars. His normal shoulder length frizz was twisted in braids, he was rocking a Canadian tuxedo of a paisley print denim jacket, star print denim jeans, and white Louis Vuitton trainers. He has delicate, androgynous features that were provoking Beatles at Shea and/or Mike on the Dangerous Tour levels of response from young women in the crowd, and it’s easy to imagine him moonlighting in modeling, or swapping full-time gigs and rapping on the side, sometime in the near future. It speaks to the presence and star quality he exudes, even as he engaged in much of the same every-other-line dropping his fellow rappers used as a crutch, as drill’s stitched and punched delivery is extremely difficult to perform live. The DJ cut out his vocals several times, leaving DD to showcase his natural voice and chops acapella, with no adornment. Throughout a noisy and busy night, it was a savvy display of showmanship, reflective of the scope and thrust of Here 2 Stay, isolating DD and his talent. 

It can’t be understated the degree to which Tiktok has infiltrated the contemporary live rap scene. I suppose it’s been obvious for years if you scroll the app regularly, but comes into stark contrast when you see it amongst a crowd of majority children. If your head was on swivel at the performance, literally every second from the moment I arrived, before the openers, through the moment I left following DD’s set, there were multiple kids, teens or adults clearly filming content for the ubiquitous app on their phones. I was able to perch just over the headline of the crowd, and it was a sea of Yankee fitteds dotted with children on their parents’ shoulders, holding their phones with the cameras on and running through a series of phrases that are rapidly becoming canonized as TikTok’s vocabulary of physical movement/pop dance. The crew on stage fed into it. I can say I’ve never seen the level of audience engagement in my life at a rap show. The rappers were not only constantly reaching into the front rows for pounds during the performance, but would work methodically along the front line, grabbing outstretched phones, turning away from the audience, and taking selfies, while performing, then handing the phone back to its owner, over and over and over again. 

When I think of the show, what I’ll remember is a dad covertly sharing a vape with his teenage daughter, kneehigh kids darting in and out of the crowd playing tag with one another like it was Prospect Park on a Sunday afternoon, and the DJ both before and during DD’s set, leading the crowd in call and response chants honoring the memory of Notti Osama. DD respected his hard cut off at 10, and even as the crowd urged for an encore, they accepted that the night was over and headed to the exits cordially. 

What I realized is much of the shit talk being traded on the drill scene is a new variation of an ancient tradition as old as rap itself, and linking it to Notti’s tragedy diminishes that loss, and DD’s career, and a community of artists being forced to answer for situations and generalities they have nothing to do with. To be a good journalist, to be a good listener of the art, to be a good person, means constantly checking your assumptions, to reject the narrative the respectable media regurgitates from what they are spoon fed by the NYPD. It’s a problem DD makes a convenient mascot for, but applies to an entire generation of young New Yorkers.

On my way down West 16th Street after the show, I passed groups of children filming TikToks while their parents served as camera people and cinematographers. Every so often I’d make eye contact with one as I gingerly tiptoed around the shot, and several looked up from their phones while holding them steady, smiled, and made the same “What are you going to do?” sheepish shrug. I nodded to each, returned the smile, and kept it moving.