Fictional cat created in 1933 to appear in magazine advertisements for the Chesapeake & Ohio Railroad, promoting their sleeping cars specifically, and using the slogan "Sleep Like a Kitten." She was a gray-and-black tabby, depicted resting in a sleeping car berth, her head on a pillow, one paw sticking out from under the covers, one eye closed, and the other eye open a crack. However, one of the most famous advertisements showed her sleeping under the bed, having given up her usual spot for the benefit of a World War II serviceman.
Later advertisements introduced two kittens, and then the kittens' father, named Peake.
When Chesapeake & Ohio's passenger service was retired with the creation of Amtrak in 1971, Chessie was retired, but she was back one year later when, following several mergers, the railroad was renamed Chessie System, and the logo included Chessie's outline inside the "C."
The Chesapeake & Ohio published a calendar every year featuring pictures of Chessie; the calendars were very popular, and are still published today by the Chesapeake & Ohio Historical Society.
Not coincidentally, my cat, who is a cross between a gray-and-black tabby and a Siamese, is named Chessie. However, I have yet to see her sleeping in the same position as the fictional Chessie.