This article celebrates the 50th anniversary of the introduction of John L. Holland's (1959) theory of vocational personalities and work environments by describing the theory's development and evolution, its instrumentation, and its current status. Hallmarks of Holland's theory are its empirical testability and its user-friendliness. By constructing measures for operationalizing the theory's constructs, Holland and his colleagues helped ensure that the theory could be implemented in practice on a widespread basis. Empirical data offer considerable support for the existence of Holland's RIASEC types and their ordering among persons and environments. Although Holland's congruence hypotheses have received empirical support, congruence appears to have modest predictive power. Mixed support exists for Holland's hypotheses involving the secondary constructs of differentiation, consistency, and vocational identity. Evidence of the continued impact of Holland's theory on the field of counseling psychology, particularly in the area of interest assessment, can be seen from its frequent implementation in practice and its use by scholars. Ideas for future research and practice using Holland's theory are suggested.