To what extent does the Anglo Cluster remains a cultural cluster in today’s managerial and professional workforce? Across six Anglo countries (Australia, Canada, New Zealand, South Africa, U.K., and U.S.), we found significant differences in values orientations (openness to change, conservation, self-enhancement, and self-transcendence values) that challenge the concept of a cohesive Anglo cluster. We also explored the influence of micro-level factors on values orientations and found consistent life-stage and gender differences across countries. We conclude that, even within a group of countries perceived as similar, multi-level analyses are needed to fully capture the essence of values differences across and within countries.