Like most countries around the world, Wales saw a flowering of popular music in the 1960s. Following the ubiquitous contemporary Anglo-American model, the popular music that emerged in Wales during that decade signalled a number of cultural shifts, both musical and linguistic. This chapter surveys the roots and developments of Anglophone and Welsh-language popular musics from the 1960s into the twenty-first century, focusing on shared traditions, political engagement, the attitudes of the ‘official’ institutions of both Welsh- and English-language culture (including the eisteddfod, the chapel and the media), and the impact of Welsh devolution; and revealing Wales’s contributions to fifty years of global musical dialogue. It considers the careers of several Welsh stars who ‘crossed over’ into the Anglo-American mainstream, including Shirley Bassey and Tom Jones, and the rise of the bands of the so-called ‘Cool Cymru’ era - prominent among them Catatonia, Super Furry Animals, Manic Street Preachers and Stereophonics. These bands achieved a new level of sophistication and cultural importance for Welsh pop, the clearest signal of which was the release of Super Furry Animals’ internationally acclaimed album Mwng (2000), a collection of songs sung entirely in the Welsh language. Post-devolution Wales has offered a greatly enriched cultural environment and infrastructure for pop music that has ensured the mainstream success of a new generation of Welsh artists such as Gwenno.