Japan has a unique role as a niche market for “entertainment work” in the Philippine labour export enterprise. Filipinos first started working there as relatively highstatus musicians (kashu) in the 1800s, and continued in such roles during WWII and into the post-war era of United States occupation. But towards the end of the 1970s, the status of migrant Filipino entertainers underwent a transformation, as they became increasingly numerous, overwhelmingly female, and part of the world of mizu shobai (literally “water trade”), as the night-time urban bar scene is euphemistically known. This paper investigates the relationship between this new influx of female entertainers-cum-sex workers, referred to as Japayuki, and twin development strategies initiated by the Marcos regime: promotion of tourism (including “sex tourism”) and related cultural activities; and labour export. It analyses the link between the Japayuki phenomenon and the education reforms introduced during Marcos’ “New Society” experiment (1965–1986) and further elaborated by succeeding governments—especially the mechanisms for certifying women as qualified entertainers. A major factor identified here is the decentralisation (and segmentation) of the country’s education system, completed in 1994, which have made it vulnerable to patronage politics and corruption. This is illustrated in the case of the 2004 Japayuki certification scandal, which shows how the technical-vocational education sector was rendered complicit in legitimising the export of Filipino labour for semi-illicit employment in Japan.