Show & Prove: DD Osama
Words: Grant Rinder
Editor’s Note: This story appears in the Winter 2023 issue of XXL Magazine, on stands now.

Hip-hop is a young man’s sport, depending on who’s asked, and that sentiment is supported by one of the current teen sensations dominating the drill scene. Harlem native DD Osama, who recently turned 17, has racked up staggering streams and YouTube views with menacing records like “40s N 9s,” “Dead Opps” and “Notti Gang.” Then there’s “Letter 2 Notti,” a heartfelt dedication to his slain brother. DD Osama has also earned teen heartthrob status thanks to a passionate female audience, which hasn’t been seen for an emergent drill rapper since Pop Smoke.

“I’m not just no regular drill rapper,” the rap newcomer declares. “I do everything, you feel me?”

DD Osama, born David Reyes, always saw himself on the stage as a kid. He’s a product of the Sugarhill section of Harlem. Playing in the park was usual for him and his siblings despite his neighborhood’s rough surroundings. His younger brother Notti put him on to the sounds of Polo G, Lil Keed and Hotboii.

With Notti showing an interest in rapping in 2021, DD joined his younger biological brother, known as Notti Osama, and the two started making music. DD began recording that year, but didn’t take the craft seriously until the following year. “We was going back to back,” he remembers of recording his first song with Notti. “So, once I realized I knew about how to rap, it was all up.”

Brimming with youthful energy, DD’s early songs showcase an effortless charisma on the mic. Though that music has a distinct New York swagger, the rising artist has always had a wide array of influences from rap’s map, including Lil Durk, Rod Wave and Lil Baby among his all-time favorite artists.

DD’s story has been dotted with tragedy like many young New York City rappers who cut their teeth in the visceral, often violent drill scene. Notti was killed after being stabbed in an altercation at a subway station last July. DD himself gained traction following his younger brother’s passing partially due to the coverage and comments it garnered in the news and on social media, an unfortunate illustration of the grim voyeurism tied to drill music’s mainstream rise. “Everything for Notti,” DD writes on every Instagram post as a salute to a shared dream of rap stardom.

Notti died on July 9, 2022, and both the collabos “Dead Opps” with the late rapper and the Sugarhill Ddot-assisted “40s N 9s,” which makes use of singer Ne-Yo’s classic “So Sick,” were released within days and weeks of Notti’s passing. Those songs caught fire on social media, namely TikTok, and DD quickly earned the attention of industry insiders and rap stars.

Last September, DD signed with Alamo Records, and by November, Drake had chosen DD as a model for a NOCTA holiday collection through Nike.

DD has been candid about how losing Notti has made it difficult to enjoy the success he’s already achieved. He’s focused and frank when he talks about his career, making his new livelihood sound like an obligation.

“I just realized I really gotta rap,” he explains. “If I don’t, who gon’ do it for me? My son Notti’s not here to rap, so I’ve gotta rap, you understand?”

Cementing himself as one of rap’s rising stars, DD spent the rest of 2022 and the beginning of this year releasing a handful of successful singles, including “Throw,” a collaboration with New York drill lightning rod Lil Mabu, and the comparatively tender cut “Upnow” with Coi Leray. These tracks set the stage for Here 2 Stay, DD’s debut mixtape released in May, which finds him pointedly expanding beyond drill, dabbling in Jersey club, collaborating with Rylo Rodriguez and ATL Jacob, as well as a longtime personal favorite in Lil Zay Osama.

Like a high draft pick thrust into a starring role from day one, DD occasionally stumbles on disjointed records like “On Hots 2,” but he’s hardly precious about the project. “I don’t really like that mixtape,” he admits.

On “Letter 2 Notti,” the poignant closing number on Here 2 Stay, the young rhymer shows a range of emotions, from pure grief (“I lost Notti, I lost myself”) to resilience (“It ain’t over Notti, I’ma do this for you and mommy”) to unbridled rage (“Lot of n***as gon’ die ’cause they talk on your name”).

“I’ve seen it with a lot of artists where it’s like, ‘I can’t talk to the homies, but the one person that listens every time is that booth and that microphone,’” says Tavis Chaguay, VP of A&R at Alamo. “[DD Osama is] bleeding on the mic and on the pad, you know? We’ll get a lot more of these records, but they’ll be a little bit bigger, a little more upbeat hooks and things of that nature as we go forward into this next project. On this next project, you’ll be surprised. It’s very upbeat.”

DD is genuinely committed to broadening his sound. In his recent and upcoming releases, the rapper and his team have sought to stay away from some of the darker aspects of drill, a decision that feels both strategic and poignant given that Brooklyn rap group 41’s “Notti Bop,” a viral track mocking the death of DD’s brother, is among the most disrespectful and unnerving songs in the drill space.

On the positive side, DD has played headlining shows, receiving a rapturous response in London and Chicago. He also joined Lil Durk for some dates on the Sorry for the Drought Tour before a majority of dates were canceled earlier this year. Besides talking about the label they’re signed to, DD reveals he’s “learned a lot” from Durk. “Man, that boy smart,” he says of Durkio. “He different. He’s a genuine, real-ass n***a. I ain’t gon lie.”

DD Osama wants to work with Lil Durk and Sexyy Red on his next release, though DD is characteristically hesitant to share concrete details about it. He dropped the music video for his Luh Tyler collab “Pup” this past August and “Macarena” featuring bars from the late Notti. Both may likely appear on a forthcoming project.

“I’m dropping two more mixtapes, and then I’ll probably drop an EP and then two mixtapes and then my album,” DD states. Chaguay adds that the plan is for at least one of those projects to be released “on this side of the calendar year.”

Currently, he’s doing whatever is needed to succeed. “I just be doing everything so I can evolve and get better,” DD conveys.

Keep going.

DD Osama photo
Tyrel Brown

Read DD Osama's interview in the Winter 2023 issue of XXL Magazine, on newsstands now. The new issue also includes the cover story with Latto and conversations with Killer MikeFlo MilliMaiya The DonMonaleoMello BuckzzSexyy RedBigXThaPlug, plus more. Additionally, there's an exclusive interview with Fetty WapQuality Control Music's Coach K and P discuss 10 years into the label's growth, and in-depth stories on the popularity of sampling in hip-hop in 2023 and the state of hip-hop touring, and the best moments of hip-hop's year-long 50th anniversary celebration.

See Photos From Latto's XXL Magazine Winter 2023 Cover Story