“It’s a beautiful art, but it’s pretty morbid,” he said. Often, the T-shirts he designs are for the very young, frequently victims of gun violence. “I love airbrushing, I love graffiti, but I’d rather make shirts to celebrate a graduation or a wedding, or, hell, even a picture of somebody’s dog,” he said. “But it is what it is. It’s tough.”
When he started airbrush designs, in the early 1990s, the style was to present figures in dark, absurd cartoons, as popularized by the Shirt Kings, two graffiti artists from Queens. With creations worn by the likes of Jam Master Jay, LL Cool J and other East Coast heavyweights, the Shirt Kings rose to prominence and helped to embed custom graffiti-inspired artistry into hip-hop fashion.
The origins of the airbrushed T-shirt worn in memoriam are nebulous. It’s likely a derivation of the second line funeral processions of New Orleans. Ronald Barrett, a scholar of black American rituals of death, attributed the practice to a West African tradition in which mourners carried handkerchiefs, scarves and other ephemera bearing the names and faces of their dead.
Visual memorials peaked in the ’90s, with the deaths of hip-hop superstars inspiring a deluge of murals and public graffiti art, especially within the cities they were associated with. But as municipal sanctions began to limit public graffiti — a Chicago ordinance prohibiting the sale of spray paint was passed in 1992 and affirmed by the Supreme Court in 1995 — the T-shirt was available as a miniature, and more personal, canvas.
In the early 2000s, the death of Aaliyah, followed by Lisa Lopes (known as Left Eye) and Jam Master Jay in quick succession, heralded a mini pop-culture renaissance of airbrushed designs worn as homage. Those designs seemed motivated by the challenges of hyperrealism, 100 percent airbrushed representations that, at first glance, seemed more photographic than painterly. It was around this time, in 2002, that Mr. Virgin, who opened the shop with his uncle, now deceased, met Mr. Ray.
Over the years, the cut of the shirt has shrunk. The 100 percent cotton extra-tall tees of yore proved not ideal for airbrushing. The natural fibers hold but don’t really absorb the paint, with the material remaining on the surface of the shirt in a way that leaves it prone to cracking and fading. Mr. Ray prefers lighter polyester blends, not tubular, with a crisp side seam to guide and bifurcate the shirt’s front and back.
Often, design sessions run into the night. Each shirt is a hybridized creation; Big City uses a combination of spray paint, sublimation (direct-to-garment printing), dyeing and screen printing. Heaven, and its symbolics, and the jagged Chicago skyline are most-requested motifs, and they are rendered with an almost rococo decadence. The scenes sprawl out behind the central photograph for a surrealist, multidimensional effect. On one shirt, the John Hancock building is interpreted with such precision that its famous x-bracing steel beams are visible.
Mr. Carnegan, Big City’s graphic designer, believes that the airbrushed design tribute is nearing an explosion. He said that the practice will go national and mainstream, “in like 2 or 3 years.” He is pessimistic about the implications of this for Big City. “They’ll be in H&M maybe, or Zara. Somewhere where people can get them cheap and quick,” he said.
The resurgence of a variety of kitschy ’90s nostalgia is to blame. In early 2015, Drake, perennial soft boy nostalgist, posted at least one photo on Instagram of himself wearing a shirt featuring an airbrushed portrait of Selena Quintanilla.
In February 2016, the commemorative tee went high fashion, or at least aspired to, when it was worn, and briefly sold, by Kanye West after the joint presentation of his Yeezy Season 3 collection and “The Life of Pablo” album. The stone-colored tee features his mother, Donda West, airbrushed back to life on its front. The shirt’s back is a smiling Robert Kardashian, Mr. West’s wife’s dead father. “In loving Memory” is wreathed above their heads. The airbrushed T-shirt, long consigned to the twin bastions of leisured Americana — malls and West Coast boardwalks — was “back.”
One of the perils of mourning in a cultural moment largely choreographed by social media is the slip into pageantry, with all the attendant competitiveness. “Some of these kids, man, it’s scary,” Mr. Ray said. “They get T-shirts, dog tags, all types of memorabilia, their rooms and lockers look like shrines. It’s like, I question whether that’s healthy.”
There is also the hazard of conferring affection for a person onto an object, something that is ephemeral; threads will unravel, paint will fade. Despite their own life spans, the shirts also function as a refutation of the supposed anonymity of gun violence. That number — of victims — is often deployed with a rote disregard, especially in relation to Chicago. The shirts serve as a declaration of the singularity of death as well as that of grief.
In 2002, Karla F C Holloway, a professor at Duke University, wrote, of black “commemorative conduct”: “Our daily lives were so persistently interrupted by the specters of death that we worked this experience into the culture’s iconography.” She suggests that the open-coffin funeral and the street corner memorial point to a type of mourning, which was, out of necessity, constant and protracted.
These practices, like memorial T-shirts, serve multiple aims. They are a memorial to both the deceased and to the ways they died. And all of these practices function as an indictment, where the law has provided none.
In 2014, Lesley McSpadden — the mother of Michael Brown, the 18-year-old who was killed by the police officer Darren Wilson in Ferguson, Mo. — was photographed on the weekend of her son’s funeral in a memorial T-shirt bearing her son’s visage, in his graduation cap and gown, next to her own. The photograph of her on the shirt is from soon after his death, and her face is wrinkled in sorrow and horror. The words “He Was Special 2 Me” are emblazoned across the shirt in rubescent detail.
In a 2015 article about black mourning in The New York Times Magazine, Claudia Rankine wrote that the images featuring Michael Brown lying dead on the asphalt (a tableau that would later be recreated) were just as likely to serve as a “spectacle for white pornography” as they were to incite any sort of national mourning. Ms. McSpadden’s shirt was a counter to such images of her son. It featured him alive and stately in his graduation blue and gold. It proclaimed that his death and her grief did matter, where, for some, his life certainly had not.