In spring 2001, Richard Harris found himself at a crossroads. He was heading into retirement after 35 years selling antique prints, largely botanical and herbal, from his Chicago shop to high-end decorators across the country. At the same time, he had decided to sell his personal collection of prints by Rembrandt, Matisse and Picasso—some 85 pieces acquired over three decades—through a series of shows at C. G. Boerner, a dealer in Old Masters, 19th-century and modern prints and drawings with branches in New York and Düsseldorf.

Harris was ready to start a new collection, but this time he wanted to rely more heavily on his own sensibilities and avoid the more-traditional collecting categories. In addition to prints, he had amassed rare books in such fields as natural history and anatomy—an interest since his time as a premed student at Queens College (he switched to economics and art history upon discovering he didn’t have the stomach for medicine). Maybe, he thought, he should focus on anatomical books and prints—especially the whimsical and scientifically inaccurate images from 16th- and 17th-century Europe. On consideration, however, the topic felt a bit narrow. A more compelling vision came to him the following March, when he went to the art fair in Maastricht. Kunstkammer Georg Laue, of Munich, had staged a dramatic display of the art of memento mori, or reminders of human mortality, from a 17th-century watch in the form of a skull to 20th-century Papua New Guinea skulls decorated with seeds.

“This booth was the talk of the year,” says Harris, who at 71 speaks rapidly and moves with the nervous energy of a much younger man. “It was filled with these oddities that took me on a wonderful journey from medieval times to the present. I had found my subject.” In effect, Harris had also found an open ended approach to collecting art, one that in the spirit of the Renaissance Wunderkammer, is not bound by historical period, genre or medium. And he had found a broad theme—images of death—that complemented his interest in anatomy.

Today, Harris has a large, varied, highly personal and idiosyncratic collection of artwork featuring skulls and skeletons,which he has dubbed, rather theatrically, 1,000 Faces of Death. It comprises well over 1,000 pieces—prints, drawings, paintings, photographs, sculptures, books and comics among them. Some were intended for scientific research or medical instruction;some are religious in nature. Some represent protests against the ravages of war, and some embody other modes of confronting death.

In deference to his wife, Barbara, and to preserve their 41-year marriage, Harris displays only a small selection of his macabre and decidedly nondecorative pieces in their home (a ranch house that, like so many in the area, owes a clear debt to Frank Lloyd Wright), in Riverwoods, Illinois, about 30 miles from Chicago. He keeps the bulk of his collection tucked awayin flat files in his home office and library, with other pieces stored under his bed. He has also left acquisitions with galleries for safekeeping, including a prized early 17th-century carved-fruitwood skeleton from southern Germany, purchased at the Blumka Gallery, in New York, for $100,000.

These days, Harris’s goal is to find the right museum to exhibit his treasures. To this end he has consulted with several curators, including the former MoMA heavyweight Robert Storr, who reviewed images of the works and flagged those of particular interest. (Storr declined to speak for this article, noting that it is his policy not to promote private collections.)

Some of Harris’s acquisitions are exactly what you would expect were you to free-associate on the theme of death in art history. He owns a full set of the first edition of Goya’s 1863 “The Disasters of War”—all 80 prints in original blue wrappers—as well as Jake and Dinos Chapman’s 1999 re-interpretation of that series. Harris also has a 1945 Surrealist drawing by Hans Bellmer of a woman in a diaphanous robe with a skull coming out of her stomach and a 1958 collage of skeletal figures, Faces of Death, by the great Dada satirist George Grosz.