This essay examines pivotal instances of Taiwanese musicians’ engagement with Thai popular music beginning in the late 1980s. The essay analyzes the social and cultural inter-Asian contexts in which Thai pop songs were incorporated or recreated in Taiwan’s pop music. Examples include Thai pop music covered by anti-colonial artists in the New Taiyu Song Movement and Thai songs covered by Mandarin pop idol groups. Thai music and musicians also contributed to the creation of Taiyu electronic dance music. More recently, Thai lukthung pop started to make its way into Taiyu pop and rock, as demonstrated in the smash cover-hit of “Your Heart for My Number.” Additionally, Namewee, a polyglot musician from Malaysia, incorporated cha-cha and lukthung in the multilingual crowd-puller “Thai Cha-Cha.” With the multiple associative narratives of popular music between Taiwan, Thailand, and Asia, this paper critically reframes how popular music in Taiwan engages with Thai pop music.