The Reading Company was originally chartered in 1833 as the Philadelphia and Reading Railroad to build a line between its namesake cities. By 1842, the P&R linked the ports and markets of Philadelphia to the anthracite coal regions of Pennsylvania in Pottsville. The P&R soon expanded into a variety of other ventures from coal mining (through its subsidiary, the Philadelphia and Reading Coal and Iron Co.) to canal and ocean transport operations. In 1871, the P&R had a net worth of $170 million, making it the largest corporation in the world. Aggressive expansionism and overextension in the late 19th Century would lead the P&R into bankruptcy. As a result, the Reading Company was formed in 1893 as a holding company to own the railroad and coal companies.

The federal government soon declared the company to be a monopoly, forcing the railroad and coal companies to split. The P&R Coal and Iron Co. went on to become the present-day Reading Anthracite Company. In 1923, Reading became an operating company when the P&R and other wholly-owned subsidiaries were merged.

Through alliances with other railroads, the Reading was an important bridge line carrier as part of the "alphabet route" for both north-south and east-west traffic. In the years following World War II, the nation gradually shifted from coal to oil as a power source and traffic on the Reading began to decline. The 1968 Penn Central merger moved substantial through traffic off of the Reading, and the railroad went bankrupt in 1971.

The federal government conveyed the operating assets of the Reading into the Consolidated Rail Corporation (Conrail) in 1976. The Reading Company continued to exist as a corporate entity after that date dealing mainly in real estate. By 1993, all remaining railroad-related assets were history. The Reading Company was reorganized under a Nevada holding company as Reading Entertainment, Inc., in 1999, and the remaining Pennsylvania offices were closed in 2000.

Reading Entertainment currently operates as part of Reading International, Inc. The company operates a chain of movie theaters in Australia, New Zealand and the United States.