As a result of the recent federal health care legislation, all restaurants in the United States that are part of a chain with twenty or more locations serving substantially the same menu items will be required to post the calorie information of the food they serve directly on menus and menu boards. This development represents the culmination of a regulatory initiative to combat the growth of obesity that only began in 2006 with the decision by the New York City Board of Health to require calorie posting in New York City chain restaurants. That initiative, Regulation 81.50, was the first of its kind in the United States; and yet, less than four years later, the idea has become a national standard. This paper tracks the history of New York City's landmark regulation, detailing the drafting of the law, the initial legal victory for the restaurant association challenging it, and the ultimate triumph of the City in winning legal validation of its calorie posting mandate. In doing so, this paper will also use the New York City regulation as a launching point to discuss the rationale behind menu labeling, to examine the potential legal pitfalls of menu labeling laws, to track the development of the initiative from New York City to a national standard, and finally, to evaluate the preliminary data on whether or not menu labeling is actually effective in achieving its ultimate goal: changing consumer eating habits and reducing obesity.