AbstractMassive “field” stars are those that appear in apparent isolation, in contrast to those in clusters. Whereas cluster stars are formed together in large aggregates, simultaneously, field stars have multiple origins. Some massive field stars may be the “tip of the iceberg” on small groups of physically associated stars, while others appear to be “runaway” stars that are dynamically ejected from clusters. What is the intrinsic relation between clusters and field stars, and what is the faction of runaway stars? Since massive stars are the most luminous stellar population, their demographics are accessible in the nearest external galaxies. We present our current efforts to understand these issues for the Small Magellanic Cloud.