Last summer, before DD Osama was being played out of every pre-teen’s Bluetooth speaker in the five boroughs, he was a relatively small-time drill rapper from the Sugar Hill area of Harlem. Along with his friend Sugarhill Ddot and little brother Notti Osama, they were a trio of baby-faced 14 and 15 year olds with a couple of no-holds-barred diss tracks to their names. Then tragedy struck. In early July 2022, 14-year-old Notti Osama was stabbed to death in the 137th Street-City College subway station. The incident rippled through New York’s drill scene, bringing a ton of attention to the trio and its music. Seemingly overnight they were sensations. Voyeuristic beef pages and online platforms, including but not limited to No Jumper, ran wild. Drake hit them up to model his newest clothing line. Labels swooped in with heavy briefcases in hand.
In the meantime, Notti’s death was callously turned into a punchline, most infamously by the attention-hungry viral hit “Notti Bop,” a song and dance mocking the way he died. Dark turns are inevitable in a subgenre that’s become the go-to outlet for the youngest residents of the most depleted and underserved corners of New York, but this was a new low. Now 16, DD Osama is the current most popular New York drill rapper not named Ice Spice. He commands a different type of fandom than previous title holders like Pop Smoke and Sheff G; those artists were older by a few years, which is a lot at that age. DD is beloved by kids who are still years away from getting into R-rated movies. Recently I spent a day at a middle school in Harlem and just about the only artist they wanted to talk about was DD Osama. At his live shows, young girls scream like he’s on the cover of Tiger Beat and adult chaperones mill around in the background. The dissonance couldn’t be louder on DD’s eerie new mixtape Here 2 Stay, a debut that’s trying to be drill’s version of My World 2.0 and process grief at the same time.
Understandably, DD is not entirely sure how to handle all of this. Songs that are supposed to be loved-up teenage pop-rap actually sound melancholy and fatalistic, even when they’re trying not to. On “Who I Am,” he flatly sing-raps about a girl that he’s fallen for. The song clearly wants to have the slick tone of “Yo (Excuse Me Miss)” but is unintentionally more like “Heart on Ice” as he lilts, “Been through a lot and I ain’t tryna’ lose you/Lost my brother this shit feels unusual.” Likewise “Be Alright” is a romance where everything is going pretty much fine in the lyrics yet the miserable-sounding ATL Jacob beat and DD’s quiet, cracking voice makes the depression feel inextricable.