Dental caries is the most prevalent oral health disease and affects the health of individual and populations. The conventional disease metrics do not represent the impact of caries on people's lives. Oral-health-related quality of life measures were developed to help understand which aspects of dental caries have the greatest impact on well-being. How these measures were developed follows a standardized process of development and testing, with the ultimate aim of the entire process being that they be used in clinical dentistry, dental epidemiology, and health services research. There has been ongoing debate about whether these measures have adequate discriminative ability for the wide range of caries experience, and whether they are responsive to changes in disease experience. Whether these measures are "perfect" or not, what we do know after two decades is that numerous studies have found them to be sufficiently discriminative for caries in adults and children alike. There is also evidence for their responsiveness, chiefly from studies of children undergoing dental treatment under general anesthetic for early childhood caries. The influence of environmental, social, and psychological characteristics is another consideration in how people self-rate their oral health. Is there a need to improve the quality of these measures by refining existing ones or developing new ones which may represent those broader concepts? Regardless of the future, the most pressing challenge is the need for health systems work to ensure the routine use of these measures in clinical and public health practice.