Many country songs have been recorded about waitresses, including Ray Pillow’s “The Waitress” released on Mega Records in June 1971 (reaching #67 in Record World magazine). Opening with a pair of twanging, mournful guitars, and lean percussion, Ray’s narrator sadly describes the challenging life of a waitress who has to deal with the mundane and degrading aspects of waiting on male customers.

We soon learn that the narrator is describing his ex-wife, who “learned to be a waitress, from sittin’ home and waitin’ on me.” Waiting in this case is not just subservience, but waiting alone at home as he spent nights away, working, or perhaps carousing and cheating on her. There is a tinge of guilt in the narrator’s descriptions of his ex-wife, who works “in some lonely city” and has grown “tired of truckdrivers telling her she’s pretty.” The waitress is strong and patient, though, heartbroken but wise. 

A recurring character in country music of this era is the woman whose dreams are disrupted because of a man who can not settle down (or who tried but failed). Pillow’s narrator acknowledges a bitter truth about his ex: “She’s got much more to give, and less chances of getting what she’s after.” Although he seems empathetic, a truth that eludes him is that he took what made her most appealing to other men like him–her youth and her virtue. 

Pillow imbues the narrator with a shade of pride in his wandering and inability to stay with one woman, inferring perhaps that his emotional baggage may have strengthened his wife to go on with her life in such an independent, perservering manner. The “fleeing” men so common in classic country music must in some ways justify their own choices even as they regret them, and if their own escape from the women who sought from them a settled-down life can be viewed as a good thing, all the better: the idea can make their independent, aimless wandering more palatable, while they circle in on their next always-temporary home. 

Reminding us of 1967's “Branded Man” in which Merle Haggard’s ex-convict is forever running – from the law, from every woman who cared too much – the theme of being and staying on the run indeed runs rich through the veins of classic country music, the achievement of which makes these men both very satisfied, and very much alone.