Star clusters are privileged laboratories for studying the evolution of massive stars (OB stars). One particularly interesting question concerns the phases during which the classical Be stars occur, which—unlike HAe/Be stars—are not pre-main-sequence objects, nor supergiants. Rather, they are extremely rapidly rotating B-type stars with a circumstellar decretion disk formed by episodic ejections of matter from the central star. To study the impact of mass, metallicity, and age on the Be phase, we observed Small Magellanic Cloud (SMC) open clusters with two different techniques: (i) with the ESO–WFI in slitless mode, which allowed us to find the brighter Be and other emission-line stars in 84 SMC open clusters, and (ii) with the VLT–FLAMES multifiber spectrograph to determine accurately the evolutionary phases of Be stars in the Be-star-rich SMC open cluster NGC 330. Based on a comparison to the Milky Way, a model of Be stellar evolution, appearance as a function of metallicity and mass, and spectral type is developed, involving the fractional critical rotation rate as a key parameter.