The Old Jail Art Center (OJAC) opened in 1980 with four small galleries, in the first permanent jail built in Shackelford County. The jail was designed and built by the civil architect John Thomas of Thomas and Woerner, Builders, Fort Worth. Construction began in 1877 and was finished the following year at the cost of more than $9,000, which outraged the local taxpayers. Scottish stonemasons carved their initials into the building's large limestone blocks, in order to ensure payment for work done once the fledgling county was solvent. You can easily see why the building was known for several decades as "the alphabet jail." The "M" and the "E" are known to be the initials of stone masons named McGuire and Emery, while the "X" and the triangle are thought to be the marks of illiterate stone masons. Considered very modern at the time of its construction, the jail was used for more than half a century until it was abandoned in 1929 in favor of the "new" jail one block to the west. Robert E. Nail Jr., Princeton graduate, local author and playwright, most notably of the Fort Griffin Fandangle, saved the building from demolition in 1940 by purchasing it for $25. He bought the lot on which it sits for $325 a few months later. One of the few outstanding examples of nineteenth-century Classic Architecture still in existence, the structure was added to the National Register of Historic Places in 1976.

Reilly Nail, Princeton graduate, local author and former television producer, inherited the old jail building from his "Uncle Bobby" in 1968. A little more than a decade later, Reilly and his cousin, the artist Bill Bomar, decided to combine their collections of twentieth-century art, and the collections of their mothers, both of whom loved Asian art. These four collections formed the core of the permanent collection, which numbers more than 2,200 art works to date. Of special interest is Jewel Nail Bomar's collection of ancient Chinese terra-cotta tomb figures which are on permanent exhibition. The collections now include works by well-known artists such as Pablo Picasso, Paul Klee, Amedeo Modigliani, Henry Moore, John Marin, Alexander Calder, Grant Wood, and many more. In addition to the fine art collections, the OJAC includes Sallie Reynolds Matthews' historical and Watt Matthews Ranching collections among its many assets. The permanent collection is best described as "eclectic” as it also contains a sizable number of works by modern British artists, Taos Moderns, Fort Worth Circle, as well as the William O. Gross Pre-Columbian Collection.

Rapid growth necessitated additions to the museums in 1984 and 1996 with another modest addition in 2009. In 2016, a new Robert E. Nail Jr. Archives addition was opened thanks to the generosity of a local family. All were designed by Fort Worth architect Arthur Weinman. Today the OJAC encompasses some 17,000 square feet and is a thriving, widely-acclaimed art museum dedicated to the visual arts and to preserving the regional history. Since 1989, the OJAC has been included in the select group of museums nationwide that are accredited by the American Alliance of Museums.