In the East End of Pittsburgh, inside an eruv, a ritual enclosure installed by some Orthodox Jewish communities to allow for freer movement during the Sabbath, is a neighborhood of roving green lawns and 19th century architecture. Squirrel Hill is one of the more beautiful areas of the city, its quiet streets lined with beech trees and spacious family homes built long before its current residents were born. It's an affluent neighborhood, with median home prices hovering around $600,000 —considerable for Pittsburgh. The tight-knit community was once even home to Fred Rogers, the greatest neighbor who has ever lived.

Pittsburgh is less a city than it is a collection of small communities divided along arbitrary lines. Drive a few miles on Penn Avenue from Downtown to the outer edges of the East End, and you'll pass through at least five of them, likely without realizing it.

Three miles from Squirrel Hill, also in the East End, is a neighborhood called The Hill District, which was dominated by Black-owned businesses until the 1950s, when local governments decided that it was in dire need of economic redevelopment. Buildings were razed , 8,000 residents (the majority of whom were Black) were displaced, and the Civic Arena, home to the Pittsburgh Penguins for 43 years, was built in their place. The neighborhood never recovered, losing over 70 percent of its residents during the subsequent decades. Today, abandoned houses and storefronts sit between overgrown patches of land. Nearly half the remaining residents live below the poverty line, according to US Census Data.

"Wiz opened the door for everyone," Quentin Chandler Cuff said. "All of Taylor Gang." Quentin, who goes by Q, is a friend and former business partner of the late Miller. He now tour-manages EarthGang, a hip-hop duo from Atlanta. "Looking up to those guys I think inspired a lot of not only artists but managers, producers, engineers, etc."

Despite its serene atmosphere, Squirrel Hill gave birth to some of the most groundbreaking rap music that came out of the city in the aughts. Along with its adjacent offshoot of Point Breeze, it was the childhood neighborhood of Malcolm McCormick, better known as Mac Miller. Miller attended the neighborhood's high school, Taylor Allderdice. Before Mac, the high school also set the stage for Wiz Khalifa and the beginnings of Taylor Gang, his record label and entertainment business.

"If last year hadn't happened, we'd probably be having a whole different conversation,' said Ian Benjamin Welch, who raps under the name Benji. Like many of the young hip-hop artists Noisey spoke to for this story, he feels as though Pittsburgh’s momentum as a rap incubator has stalled, that the spirit of solidarity that once defined it has all but disappeared. "If we hadn’t lost Mac and Wopo, you might be talking to like 20 of us all together right now."

At the start of the year, Pittsburgh had claim to one of the most revered and respected artists in the world of hip-hop, as well as one of its brightest rising stars. Before the leaves had turned, the city had lost Mac and Wopo. Pittsburgh's budding hip-hop community was left wounded and wondering how, if at all, it could recover.

Mac left Pittsburgh when his music career took off, opting for the sunnier weather of Los Angeles over the dreary Pittsburgh skies (the city sees only about 160 sunny days per year, though, as a resident, this number feels shockingly high). Smart opted to stay in Pittsburgh as his music began to explode, enjoying the fame that came with being a local legend.

Ian started rapping a couple of years ago, under the name Sir Courtesy, then switched up his style and became Benji. in 2018. Smile, You're Alive!, his record from last year, helped Benji. distinguish himself within a crowded field of rappers in the city. In addition to write-ups in local media like City Paper and WYEP , he's one of the few rappers here who can command a crowd on his own, without having to be part of a larger billing.

Welch isn't especially tall, but he stands out, with a squat, athletic build from his days as a long jumper and triple jumper at Duquesne University and flowing dreadlocks that frame a round jaw and radiant smile. He has a show tonight at Cattivo, a Lawrenceville staple that has been home to artists from marginalized communities for over 20 years, including hosting some of the best drag shows in the city.

"It's competitive now," he said. "Everyone's been watching this whole time. And, like, everyone knew that but didn't really speak on it." In Benji's eyes, Mac's continual stardom and Wopo's breakthrough represented a new chapter for the city, where the talent would finally be recognized as Pittsburgh became a more prominent hub for exciting rap music. Now, he said, the talent is still here, but it's aimless.

As a result, Benji. said, multiple rappers are vying to be the next torchbearer for the city, operating under the belief that there are a limited number of spots.

Once the hierarchy of the scene was disrupted, Benji. said—Mac Miller and Wiz Khalifa at the top, with Wopo clearly the next to break big—the direction for the city was lost. It's a fairly simple matter of marketing: With more Pittsburgh rappers making names, the scene would attract more attention, along with that attention came increased opportunities for local artists, including introductions within the industry, opening slots on tour, and features on songs. Benji. himself had been invited to open for Mac Miller on the Pittsburgh stop of his tour, an opportunity that did not come to fruition due to Miller's untimely death.

Before the tragic loss of Wopo and Mac, Benji. said, the scene was unified and coming into its own. Artists were collaborating and supporting each other, no longer burdened by the pressure of being "next up," since there were already titans putting on for Pittsburgh. The last year has changed things.

Benji. hails from Homewood originally, a neighborhood that, despite being on the opposite side of town, has a close and historical kinship with Wopo's Hill District. When the city razed housing in the Hill for the Civic Arena, many of the predominantly Black families that were displaced moved to Homewood, a shift that, along with increased white flight from the neighborhood, caused an increase in the Black population from 22 percent in 1950 to over 60 percent by 1960. In the aftermath of the 1968 Pittsburgh riots, the housing and businesses in the neighborhood were ravaged. Now, roughly 25 percent of residents in the neighborhood live below the poverty line, and Homewood South has the highest homicide rate in Allegheny County.

Benji., for his part, said he largely avoided gang life by staying active in athletics and his church. "We had our little secluded area," he said about the block he grew up on. "Me and my brother, we weren't really out in the neighborhood."

Benji.'s rap is freewheeling and sunny, even while tackling heavy subject matter. But Smile, You're Alive! captures Benji. at his lowest point. Three days before his best friend committed suicide, a paternity test revealed that the child he was expecting with his girlfriend wasn't his. A mission statement of sorts for the album, opener "Rain Down" sees him processing his heartbreak, devastation, and continued search for the beauty of existence through upbeat, poppy instrumentals and a voice that at times oscillates between pitches within the same syllable. "It's okay to be nervous," he raps. "It's ok to feel worthless / cause then there’s people like us around who remind you you're worth it."

This mentality is rare in Pittsburgh rap, where most of the music is bleak—albeit presented with the signature gallows humor of a depleted Rust Belt city. Wopo provided myriad examples of this in his work, like when he subverted childhood cartoon characters in rhymes about murder on his signature hit, "Elm Street": "On my Pokemon shit / I let it peak-at-you_._" PK Delay, a younger rapper hoping to carry a torch for the local trap scene that Wopo helped put on the map, contrasts a flow that is dreamy and distant with the staccato of 808s and gritty lyrics. On "Cold Heart," a track from 2018's Pretty the Pico, he raps "You might be my son, I ain't doubting you / You might be my son, I ain't proud of you."