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Even when you’re one of the hardest working rappers in the District, you’re not supposed to be working this hard.

“Louder!” XO shouts, trying to hype up the festival crowd, even though they probably wish they could be bouncing to “Versace.”

Louder!

It’s been five years since Diamond District, XO’s trio with fellow locals yU and Oddisee, put out In the Ruff, their local-landmark debut, and nearly a year since they last performed together, when Oddisee pulled his bandmates onstage during a cozy nightclub gig last September. Back in 2009, Diamond District had given the whole notion of the “DMV”—of a city and a region that rappers could be proud to rep—its best local argument to date. They were a D.C. supergroup before it was a city that could produce superstars.

Now, a month out from the release date of March on Washington, its second album, Diamond District is playing its biggest show ever, and the waterlogged audience is shrugging. Even on a rainy day, the crowd at homegrown Trillectro Musical Festival on the RFK Stadium grounds wants to turn up, not listen to brainy rap lyrics.

Every group needs its warm-up gigs. In Diamond District’s case, the members have solo careers, and Oddisee spends most of his time performing on the road and living in New York, so they don’t link too often these days. You’d think they’d want to get in fighting shape in front of a friendly crowd of head-nodders, backpackers, and open-mic-ers. Instead, they opted to perform a few songs at the end of the Trillectro slot of Oddisee, their highest-profile member. The new tunes are sharp—and XO cuts a dramatic figure draped in a D.C. flag—but the group sounds like it hasn’t even practiced.

For underground hip-hop fans at least, the new Diamond District album will arrive with significantly more fanfare. Their track record certainly merits the anticipation. In the Ruff landed just a month before D.C.-area hip-hop made national strides through rapper Wale’s 2009 debut Attention: Deficit. But even in a year when Wale should’ve been taking up all of D.C.’s breathing room, In the Ruff garnered respect beyond the region. Esteemed hip-hop veteran DJ Premier, whose beat for Gang Starr’s “Mass Appeal” was sampled for Diamond District’s “I Mean Business,” named In the Ruff his 12th best hip-hop album of the year. Locally, In the Ruff resonated mostly via word-of-mouth. It was one of those projects you’d discuss at open mics or with other underground rap fans who weren’t sold on Attention: Deficit’s glossy mainstream reach.

But if you craved a reunion after 2010, when the group toured Europe and then Oddisee left town to advance his production and rapping career in New York, you had to dig for the posse cuts that would occasionally crop up on their solo releases: “Delay,” from yU’s the EARN; “Do It All,” from Oddisee’s People Hear What They See; “Told You So” from XO’s Monumental 2; and “Bonus Flow,” the outro to Oddisee’s Tangible Dream. For the heads, those were all reasons to keep hoping a second full-length would eventually appear.

Now it’s finally here, but March on Washington represents something very new. “For a second, you could say we caught ourselves comparing it to the first album,” yU says. “We’re not trying to recreate the first album. That was an expression at that moment in time of how we were feeling. These are different times. This is a different moment. We’re trying to capture this moment.”

Unlike In the Ruff, which thrived on raw soul samples, March on Washington is layered with live instruments, an outgrowth of the more ambitious, collage-like approach Oddisee has taken as a rap producer in recent years. The members aren’t combative up-and-comers anymore, but earnest, reflective grown-ups. March on Washington can be a political record, like much of In the Ruff, but it’s also a back-porch record. On “Working Weekends,” the rappers tout their respective styles. “Ain’t Over” has an extended dance groove with a noticeable Marvin Gaye sample.

But there’s also the kind of rap that makes Diamond District so esteemed among local hip-hop purists: “First Step” is a triumphant mission statement with rolling synthesizers, record scratches, and hard drums. On the exultant “March Off,” XO briefly dips into national headlines, offering one of the album’s great quotables. “I’mma say what’s needed on this platform,” he affirms over a simmering organ and tumbling go-go percussion, “’cause Trayvon died in the grass, y’all.”

In the Ruff used driving instrumentals and relatable rhymes to encapsulate the pulse of young black Washington. It was a street album for intellectuals, a gritty opus for hustlers, and one of the best rap albums ever released in the D.C. area. Even as younger artists like Fat Trel, Shy Glizzy, and Yung Gleesh gain traction with the trap set and the Molly-popping masses, Diamond District plays for the region’s traditional hip-hop fans, those who want rap with substance and beats that stick past the first listen.

Oddisee, XO, and yU speak to listeners who bought rap cassettes from actual record stores, people who used to watch the Jukebox Network for their favorite videos and heard actual freestyles on TV shows like BET’s Rap City and MTV’s Yo! MTV Raps. “The Wu generation,” says Michael Tolle, CEO of the Arizona-based Mello Music Group, Diamond District’s label. Statistically, he says, listeners ages 23 to 28 are the trio’s biggest consumers, though “a lot of cats in their 30s have been very supportive.”

For those demographics, Diamond District resonates because you can identify with its rappers. Oddisee finds solace in plain adulthood and culls his material from daily observations. XO is the street philosopher with an old soul. yU speaks directly to the 99 percent; he’s the low-key worker with a modest spirit who rhymes about his family. As a collective, the members of Diamond District embody D.C.’s multifaceted ethos—the hustle, the blunt-force honesty, the resilience. They’re just as formidable apart as they are as a group.

“Diamond District has always been about three artists from the same region taking completely different life paths and career paths,” Tolle says, “then putting them together and seeing that interplay at work.”

Get to Know Diamond District

On Oct. 14, the trio of Oddisee, Uptown XO, and yU will release their sophomore album, March on Washington. Here’s a beginner’s guide to Diamond District’s music, including individual tracks from its members. —Marcus J. Moore

1. Diamond District, “I Mean Business” (2009). The group’s most popular song is a prideful stomp of hypnotic drums and pragmatic rhymes. “I keep my chin up, back straight, check my shoulders,” goes the hook. The sample of Gang Starr’s 1994 hit, “Mass Appeal,” gives the track its evocative feel.

2. Oddisee feat. XO and yU, “Gully” (2006). The first song the rappers recorded together, “Gully” is a nostalgic posse cut from Oddisee’s Foot in the Door mixtape.

3. Oddisee feat. XO, “Ride’n” (2008). “Georgetown shopping, uptown grinding, Southside riders…” XO begins on “Ride’n,” his 2008 collaboration with Oddisee, from the producer’s 101 compilation.

4. XO feat. AB the Pro, “F.R.N.O.” (2009). When left to his own devices, XO is a straightforward lyricist with brash swagger. On the anthemic “F.R.N.O.,” he rides a synthesized groove and implores you to stay real.

5. yU, “First” (2011). This track comes together perfectly. There’s the beat—a gloomy, stuttering rhythm that immediately takes hold. Then there’s yU’s flow, a determined stream of consciousness that gets more and more urgent. It’s the best 1:54 yU’s recorded.

6. Diamond District, “Streets Won’t Let Me Chill” (2009). The opener of In the Ruff set a perfect scene: gritty, cinematic, fidgety. “Erybody in the hood is either brown or black/Whites don’t come through unless they buying you crack,” XO emotes.

7. Oddisee, “I’m From P.G.” (2011). Oddisee isn’t one of those locals claiming to be from D.C. He claims Largo, Md., and reps Prince George’s County. The song says it all.

8. XO, “Black Broadway” (2010). While it’s cool to rap in D.C. these days, the District will always be a go-go town. Here, XO shouts out local icons over go-go drums.

9. Drew Dave feat. yU, “Never Burning Out” (2014). Dedicated to his recently deceased father, yU has an imagined conversation with the sun.

10. Diamond District, “First Step” (2014). The recently released March on Washington single reminds us why the Diamond District is so dope: loud drums, record scratches, and lyrics.

11. Oddisee, “Ain’t That Peculiar” (2012). The Odd Renditions EP helped sustain the national momentum after Oddisee’s 2011 breakthrough Rock Creek Park. Carried by a Marvin Gaye flip, “Ain’t That Peculiar” showed listeners that Odd can turn up.

12. XO, “Occupy DC” (2012). Back when 99 percenters were pitching tents to protest greed, XO rode a space-funk instrumental courtesy of longtime collaborator AB the Pro.

13. Oddisee feat. yU, “Still Doing It” (2011). The scenic opener of Rock Creek Park, yU preps you for the pending bike ride. The music itself is breezy and visual, and the rapper caps it with a fluid depiction of D.C.-area trails.

14. yU, “Fine” (2010). Of all yU’s songs, this one says the most and he doesn’t say anything at all. It’s just a soul-stirring loop that embodies the musician’s spirit: “We’ll be fine … we’ll be fine,” goes a vocal sample.

15. Diamond District, “The Shining” (2009). “I look around and I notice somethin’ different/Don’t know if it’s me, feel like a star in this District,” XO asserts at the top of this celebratory track. Elsewhere, Oddisee is happy to be alive and yU boasts his stubborness. Words aside, guest producer Dunc offered perhaps the best beat of his young career.

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When Diamond District formed in 2006, the D.C.-area hip-hop scene looked very different. Go-go still dominated local tastes; the city had produced a few homegrown standard-bearers and embraced hip-hop from other regions, but it didn’t have much of a sound of its own. While years earlier, local rap crews like Opus Akoben, Infinite Loop, and the Unspoken Heard carried the mantle for D.C. hip-hop, Oddisee felt D.C. needed a defining unit.

“I was at home like, ‘Man, it’d be good if we had a group from D.C.’ Because in the ’90s, we never really had one to come from the city and shout out our neighborhoods and areas using local slang,” Oddisee says. “All other cities had those records—L.A., New York, Houston, and Atlanta—but we never had one of those.”

From there, the producer/rapper (Odd’s real name is Amir Mohamed) was on the hunt for two other lyricists to complete a trio. He met yU (Michael Willingham Jr.) and XO (Jamaal Walton) at the old Capital City Records open mic on U Street NW. They collaborated on a song called “Gully,” and “during that song with them, I was like, ‘these are the guys.’” Oddisee came up with the name after hearing the term “diamond district” in reference to the city’s geographical shape.

The process of creating In the Ruff wasn’t anything glamorous. The album, Oddisee says, was completed in just two weeks after XO and yU agreed to be in the trio. “I made a whole bunch of beats, came up with subject matter and the hooks, and they put their two cents in,” Oddisee says. “We fine-tuned [the content] to meet what everybody wanted from the songs. We each wrote our verses—either together or alone—and we came to my house and recorded it.”

While the group’s collaborations slowed after Oddisee left D.C. in 2010, the rappers tried to record the new album last year, but scrapped those plans after the initial tracks didn’t come together the way they wanted. They completed the work on March on Washington in three weeks at Oddisee’s Brooklyn apartment earlier this year, working from 11 a.m. to 7 p.m., six days a week, until the album was finished in March. Just like with In the Ruff, Oddisee created the soundtrack, arranged it, and picked the topics.

“We just woke up, ate breakfast and worked,” Oddisee says. “We pretty much worked until the sun set. After that, we all hung out, chilled, came back the next morning, and did it over again.”

Oddisee doesn’t talk about March on Washington the way artists are supposed to discuss their new albums. “I don’t think a lot of people are gonna like this record,” Oddisee says. “It’s not In the Ruff Part Two, it’s not as boom-bap and it’s not as aggressive. It’s a lot more melodic, a lot more downtempo.”

But the group still has plenty of people in their corner.

They’re respected for their grounded priorities, their technical emphasis, and their old-school sensibility. “There’s a whole other community of hip-hop that goes on here,” says rapper and educator Gabriel “Asheru” Benn, whose scene-setting poem opens March on Washington. “They represent that side. I love the fact that they’re from here and you hear pieces of D.C. slang when they say certain things. I feel like I’ve watched them grow over time to what they are now.”

But with March on Washington, Diamond District is poised to make even greater strides beyond the D.C. area, says radio personality Peter Rosenberg, a host of the Hot 97 Morning Show in New York City. Rosenberg, who’s from Chevy Chase, Md., first met the Low Budget crew on his show on WMUC, the University of Maryland student radio station. “I really want more people to hear what they do,” he says. “Right now the people who know, know. It’s just a matter of ears. If people hear Diamond District, they instantly fuck with them. They have this incredible sound that is unlike anything else—and the more they work, the better it gets.”

Oddisee started rapping as a student at Largo High School. In 1998, when he was a junior, he met classmate Sean Born, who helped set the budding musician on his current course.

“We didn’t know each other, but somehow he found out I rapped or was into music,” Born says. “He tried to battle me. He was really confident like that.”

A year later, Born started building a studio in his mother’s basement. He showed Oddisee his setup—sampler, drum machine, mixer, and turntable—and taught him how to use the equipment. “He is a relentless worker at his craft,” Born says of Oddisee. “We’d make beats for days on end. I’d take breaks, do other shit, but he’d work all night.”

As Oddisee explains, he eventually tempered his work after his idol—Detroit hip-hop producer James “J Dilla” Yancey—passed away from complications of lupus in 2006. For a time, Oddisee spent 14 hours per day creating music; once Dilla died, he cut back his schedule and started exercising. “I spent the majority of my early 20s in the house, in the studio,” says the slender Sudanese-American. “I went from a six-pack and being 185 pounds to 245 because all I did was stay in the house and make music. I was very unhealthy, but extremely happy.”

To earn money in the early days, Oddisee built a studio in the basement of his mother’s house in Olney. There, he produced music for local drug dealers—who, according to Oddisee on XO’s “Told You So,” used to pay hundreds for the sessions in small bills. The producer’s first major placement was on “Musik Lounge,” a mellow cut from The Magnificent, the 2002 album by DJ Jazzy Jeff (of Fresh Prince frame). The album featured another member of the Prince George’s County–based Low Budget crew, Cy Young, and D.C. singer Raheem DeVaughn, as well as national luminaries Jill Scott and Roots bandleader ?uestlove. Jazzy Jeff had met Oddisee when he was working with Kev Brown, another D.C.-area producer, and was “blown away” when he heard the “Musik Lounge” beat.

“I found out he was an incredible MC also, and it was a done deal for me,” says Jazzy Jeff, who went on to mix Oddisee’s Foot in the Door mixtape in 2006. “I really wanted to showcase really great talent on that record, so he fit perfectly. I really can feel the soul in his music.”

Tolle also discovered Oddisee through “Musik Lounge.” The producer’s 101 compilation was the first project released on Mello Music Group in 2008. “I started the label with O as the main producer I wanted to link up with. I’d been a fan first and heard beat tapes he made in Australia for Red Bull [Music Academy] that were incredible,” Tolle recalls. “I’d buy five to 10 beats off a single beat tape.”

At 17, Born says, Oddisee was already a smart lyricist who could freestyle confidently and project his voice. But as he matured as a producer, he developed a distinctive aesthetic—nostalgic but technically forward-thinking, with lush arrangements and unusual field recordings. Meanwhile, he’s honed an image of an economy-class globetrotter with an inquisitive, big-picture point of view.

2010’s instrumental Traveling Man was created on the road, in places like Miami, London, and Sao Paulo. In early 2011, on Odd Seasons, Oddisee combined a series of four seasonal EPs into a coherent, confident set of warm sounds and chopped drum loops. Later that year, Oddisee made the biggest leap of his career with Rock Creek Park, a mostly instrumental collection of serene soul informed by the musician’s bicycle rides through the D.C. landmark. The album—created in two weeks—was partially inspired by Instagram, and it feels like it: The samples are throwbacks, the mood is gauzy, the takeaway feels personal.

“It was a culmination of me saying, ‘all right, I’m gonna cater to this trendy niche market of being in a park and shooting a photo of myself in an American Apparel polo shirt with big-rimmed glasses and a filter over top of it,” the producer says. “Then I had this reminiscent, chillwave, lo-fi music. I’m gonna couple these things together because that seems to be something people are interested in.”

Stereogum named Rock Creek Park its mixtape of the week. Since then, Odd’s music has been featured by the BBC, Pitchfork, MTV, and SPIN. His first full-fledged rap album, People Hear What They See, followed in 2012, and 2013 saw the releases of a pastoral instrumental album, The Beauty In All, and an aggressive mixtape called Tangible Dream, in which Oddisee attacked his “underrated” perception with boastful rhymes about his career breakthroughs. He’s currently working on a new solo rap album. He’s clearly hungry to find a less niche fanbase while sticking to his music’s cerebral center.

“His production now is more refined,” Born says of his former classmate. “He always liked to push and blend genres. I think he’s evolved into the artist he wanted to be back then. Seventeen-year-old [Amir] would be proud. I’m proud of him.”

By day, yU is a lyricist, father of two, and budding producer. By night, the 36-year-old works as a security guard at the U.S. Department of Transportation. Last summer, he pedaled tourists on a rickshaw to make ends meet. The Humble King’s work is never done.

On a recent summer day, a midtempo jazz break emanates from his upstairs apartment in Deanwood. Inside, yU is at an ASR Pro beat machine, tapping out a blustery instrumental.

“Just messing with some drums,” yU says.

The abode is modest, like the man. Above his workstation are visual reminders of his artistic progress: A Washington City Paper clip naming him D.C.’s best technical rapper, flyers promoting shows with his longtime producer SlimKat78, the vinyl of his previous solo album, the EARN. During interviews, yU is reserved, thoughtful, and unassuming. “I’ll play you some joints,” he says at one point, pulling out his iPhone like his music is no big thing. He clicks play, and a swell of international funk and nostalgic hip-hop pours from the speakers, saturating the carpeted habitat.

yU has a slew of music he’s finishing, including spacey songs like “Stargazing,” a great boom-bap track slated for his next solo rap album, In the Listener’s Stance. He plays a few snippets from his forthcoming instrumental set, Culture \> Couture.

At least one person doesn’t mind the racket.

“I feel like [yU] is one of the best lyricist/producers I’ve heard in a minute,” says Carl “Kokayi” Walker, the local rapper and producer and yU’s next-door neighbor. “[His] subject matter, willingness to bend the rules and care about his messaging are what makes me appreciate him.”

Not surprisingly, yU announced his Deanwood arrival in April 2013 in the subtlest way possible. “I saw him in my neighborhood on my way home,” Kokayi recalls. “He called and asked if I lived on the same block. I told him to knock on the door, my wife answered, and he was like, ‘Man, we’re neighbors.’”

The veteran Kokayi has known yU for 15 years—when, as a member of the Remainz crew with seven others from Montgomery Blair High School in Silver Spring, yU would visit the now-defunct Freestyle Union at the old Kaffa House, which used cipher workshops to teach emerging artists how to rhyme. Born in Cheverly in 1978, yU first started rapping in 1996 with a crew called the Untold Truth that performed in local talent shows.

In November, yU and SlimKat—known collectively as the 1978ers—will release the collaborative People of Today, an album with big societal concerns and meticulous depictions of various characters they’ve encountered. When yU’s not compiling his own music, he serves as a mentor to a few of the region’s rising producers, like Andrew “Drew Dave” Davidson (formerly known as Soulful!) and Drew Kid.

“He’s constantly providing me with advice, not only in terms of music, but just life in general—you know, little tips like how to better myself as a producer,” says Davidson, whose recent song, “Never Burning Out,” featured yU rhyming about his recently deceased father. “He chops drum breaks in a real unorthodox way, which is crazy to me. I watch and listen to what he does, and how he does his own production, and just try to draw inspiration from it.”

Still, yU goes largely unheralded as a producer despite having released his own instrumental project, A Garbage Beat Tape, in 2011. He doesn’t advertise those skills, even if his Instagram feed is full of self-created instrumentals and partially finished verses. He’s known mainly as a lyricist; his rhymes are always fluid and technically precise, whether he’s musing about finding employment, providing for his children, or appreciating life’s subtleties.

“yU was really a surprise,” says Tolle (the rapper’s Before Taxes, the EARN, and A Garbage Beat Tape were released through Mello). “I was blown away, like, ‘Where did this guy come from?’ He had a righteous storytelling ability that was captivating. His lyrics were truly empowering to me. I had to be down.”

As a member of Diamond District, yU acts as the calm buffer between Oddisee’s straight-laced lyricism and XO’s politically charged themes, shunning superficiality with a gray-haired wisdom that directly reflects his Suitland upbringing.

“We all have different angles,” says yU. “Naturally, we’re different people who come from different places. We have different friends, but we have a respect for each other, even though we’re on different pages.”

There’s no telling where you’ll see XO: leaving Listen Vision Studios near Howard University, hosting his open mic every Tuesday at Pure Lounge on U Street NW, in a home studio with longtime collaborator AB the Pro.

At the corner of Georgia Avenue and Allison Street NW in Petworth, XO is walking to a quaint house, where the rapper plans to spend the evening recording new tunes and chilling out with a few friends. As we’re talking in the backyard, it’s a family affair; sometimes he lets his friends answer my questions.

XO’s demeanor stems from his days as a teenager in Laurel and Greenbelt. The Riggs Park native came to Laurel High School with an Individualized Education Program—a customized curriculum for special education students—because of emotional problems stemming from the unstable living conditions of his childhood. “Everywhere I lived, I got evicted,” says the rapper, who now lives in Congress Heights. He’d get into fights with classmates and neighbors, but gained popularity from those altercations. He graduated from Eleanor Roosevelt High School in 2004, but was supposed to finish a year earlier. As a teenager, XO says, he sold pot to help his mother pay the bills, but eventually she kicked him out because of the drug dealing.

XO comes from a family of musicians—his father played drums with Gil-Scott Heron; his mother played clarinet with gospel artist Richard Smallwood—and grew up idolizing LL Cool J, the Notorious B.I.G., DMX, and Jay-Z. As a freshman at Laurel High, XO first started rapping when he jumped into a cipher with some fellow students. “I had school detention, I had to pick up everybody’s trash,” XO remembers. “There would be these New York dudes who were always the last ones leaving the cafeteria because they were in a cipher. I was always writing, but I didn’t show anybody ’cause I didn’t feel I was ready yet. But at this moment in time, I jumped in the cipher.”

By 2010, XO was a crown jewel of the local Studio43 record label, the same imprint that once had Wale on its roster of rappers. But since Studio43’s folding in 2011, XO has released much of his music independently, other than Colour de Grey, which dropped through Mello in 2013. In June, local punk label Cricket Cemetery rereleased XO’s 2008 mixtape, Takeover 2, on vinyl.

In recent years, XO has dropped an abundance of new music that exemplifies the rapper’s deep affinity for serious themes. Lyrically, the 29-year-old is a throwback to pregentrified D.C. and its “Chocolate City” pride. He raps critically about racism, classism, and the city’s demographic upheavals of the last decade.

Follow XO’s Twitter and Instagram feeds, and you’ll see opinions about the recent uprising in Ferguson, Mo., in which a white police officer shot and killed an unarmed black teenager. As he sees it, mainstream rappers aren’t doing enough to challenge political authority. “In the past, man, [NWA’s] ‘Fuck da Police’? That was a different type of go hard,” XO says. “That was a go hard that threatened the powers that be! We ain’t got people like that no more.

“I be on some soulful revolutionary shit,” XO says. “Ain’t nobody doing that. I grew up caring about things that a lot of people don’t give a fuck about. That Assata Shakur, militant, Marcus Garvey type shit.”

With the new Diamond District, though, XO scales back the social commentary to fit in with the group aesthetic. “Oddisee was like ‘X, I know you on what you be on, but be a little neutral for ’em,’” XO says. “I’m just trying to learn and get better. I know a lot people are gonna be listening. When they listen, I want them to get something that’s gonna stick.”

Backstage, before their Trillectro performance, Oddisee, XO, and yU are already in character. Odd, who came down from New York for the show and will return the same day, offers a gentleman’s handshake. yU is welcoming as usual: “How you been?” he asks. “Maintaining,” he says when I ask the same thing. XO, always affable, is revving. “EALU! EALU! EALU!” he repeats, shouting out his forthcoming album with AB the Pro.

But when it comes to March on Washington, talk is measured. It’s just a hip-hop record, they stress—nothing more, nothing less. “People overcomplicate art,” Oddisee says. “Art is for the people. If they like it, you find a way to capitalize on it. If they don’t, you go back to the drawing board.”

And what if you’re just a few too many steps ahead of the people?

“Musically, this is not what purists and hip-hop heads are gonna want to hear from us, and I think they’ll be disappointed,” Oddisee says. “But if they sit with the album long enough, they’ll understand how good it is, and then grow to like it when it’s too late.”