We tend to think of the turn of the century as a sentimental era when grown men were not ashamed to weep over musichall effusions about motherhood and infant mortality. If ever there was an age that should have paid proper respect to St. Valentine’s Day, it was this one. Therefore there is something faintly shocking about the perverse sideline on the following pages. They are valentines, they cost only a penny each, and they made many people unhappy once a year for more than a century. Comic valentines appeared in America as early as the 1820’s, and by 1840 they were being produced on a large scale. The dubious art form reached its peak in the late nineties and early 1900’s with the crude, vigorous examples shown here. The sketches attacked such vanished enemies of society as the stingy boarding-house keeper, as well as some that are still with us—the crooked policeman and the foul-mouthed teamster, for instance. After the 1920’s the tone of the missives softened, and although insulting valentines are still manufactured, the ferocious broadsides on these pages have gone the way of the mandolin, the detachable cuff, the philosophy of Elbert Hubbard, and other turn-of-the-century miseries.