In the half-century between the 1810s and the 1860s, a number of American artists—many of them self-taught—made their living by painting portraits of the dead. It was a difficult art to master. Some painters only had verbal descriptions on which to draw, and they arrived at likenesses that couldn’t possibly measure up to families’ memories. Even when they were brought in quickly enough to have a body to study, it took a formidable imaginative effort to succeed—to reconstruct what the child in question would have looked like alive and animated. In most cases, the figures they painted came off awkwardly proportioned or posed.

Once photography arrived in America in 1839, artists could capture their subjects’ likenesses unmistakably. But the kind of truth that daguerreotypes of corpses offered was bitter and potentially horrifying. Photographers needed an arsenal of rules and optical devices to offset the bluntness of the images they made. In the case of infants, Nathan G. Burgess wrote in 1855, the body should be “placed in the mother’s lap, and taken in the usual manner by a side-light representing sleep.” Older children, he said, “can be placed upon the table, with the head toward the light, slightly raised.” Opening the corpse’s eyes might seem daunting, Charlie E. Orr wrote in 1873, but “this you can effect handily by using the handle of a teaspoon.” Painters had to strain the limits of their imagination to reconstruct the features that a camera could capture in a flash, however artlessly.

Securing the Shadow: Posthumous Portraiture in America, a haunting new exhibition at the American Folk Art Museum curated by Stacy C. Hollander, shows how energetically photographers and painters competed over the power to depict the dead, particularly children lost to disease. The images these artists produced, as Hollander emphasizes in her thorough essay for the show’s catalogue, had a powerful allure in a society that bore the constant threat of illness and bereavement. As photographs entered wide use, families and artists both kept re-assessing what form these mourning pictures should take. (They have been ever since: mourning culture underwent similarly dramatic changes, for instance, when snapshots displaced more formal posed pictures and bereaved families found themselves with a fuller photographic record of their loved ones’ lives.)

It can be hard to imagine that families once found paintings of dead and reanimated children comforting. The portraits in Securing the Shadow present a world of skewed bodily proportions and blunt symbolism. Instead of redemptive visions, they sometimes inadvertently offered what look more like nightmares. Toddlers with sad expressions, oversized heads, and large eyes stare poignantly out at the viewer, usually holding objects heavy with religious or artistic meaning: a key or a Bible or a bird tied to a trimmed string. In one particularly disturbing portrait—Ambrose Andrews’s “The Children of Nathan Starr”—three of the children of a Middletown manufacturer bat a shuttlecock over the heads of a serene older girl and the young boy whose death occasioned the picture. The projectile hovers in midair, as if it was just struck, but none of the children’s poses suggest that they’ve been moving; they stare ahead blankly and stand rooted to the spot.

The painters who made these images were often themselves haunted, afflicted or eccentric figures. William Matthew Prior’s vision of the faces of three disembodied “Heavenly Children” emerging from a bank of clouds is one of the show’s most fanciful images; he had, we’re told, “lost his first wife and six of their children by the time this portrait was painted,” shortly after which he took up Spiritualism. The prolific New England portraitist Joseph Whiting Stock had been confined to a wheelchair by an oxcart accident at age eleven and would die of consumption before he turned 41. His portraits combine a probing eye for detail with a curious disregard for perspective, but their most startling aspect is the uniform expression of serene omniscience he gave nearly all the plump children he painted, as if they’d already crossed over to a new and higher level of spiritual insight. (Many of his numerous postmortem portraits, Hollander notes, he recorded as having been made “from corpse.”)