This paper examines how American vintners, restaurateurs, and wine merchandisers struggled to overcome wine’s paradoxical stigma—its highbrow mystique and déclassé reputation—and build a mass market during the 1930s, 1940s, and 1950s. Initially, wine promoters attempted to enhance wine’s respectability by instructing readers about proper serving glasses and proper food and wine pairings. When these highbrow approaches backfired, mid-century wine merchandising developed new ways to sell the glamour of wine without the demands of connoisseurship. Wine gradually lost its foreignness as mass marketers and consumers adapted wine to existing American drinking practices and middle-class visions of the good life. Wine promoters worked to both surmount and accommodate consumer preferences for spirits by alternately casting wine as a base for cocktails and as the budget-friendly alternative to them. While some have attributed the ascendance of table wine consumption in the 1970s to the converging tastes of hippies, urban sophisticates, and gourmets, I argue that wine merchandisers and a different set of consumers sowed the seeds of that “wine revolution” in the 1950s, when wine found its way to the American dinner table via the cocktail glass, the casserole dish, and the backyard barbecue—the essential trappings of middle-class suburbia.