Chessie was a popular cat character used as a symbol of the Chesapeake and Ohio Railway. Derived from an etching by Viennese artist Guido Gruenwald, the image first appeared in an advertisement in the September 1933 issue of Fortune magazine with the slogan "Sleep Like a Kitten and Wake Up Fresh as a Daisy in Air-Conditioned Comfort".

When the ad generated a positive response, the railroad developed an advertising campaign around the image and chose the name Chessie as a derivation of the railroad's name.