Premodern Japan boasts one of the world's richest and most venerable poetic traditions, with a written history dating back to about the 6 th century CE. But translations into English of its various genres, notably waka and haiku, only began to appear in the mid-19 th century. The extreme differences between English and premodern literary Japanese and the welter of classical poetic conventions have complicated accurate interpretation and translation. A historical overview of representative examples reveals a trajectory from heavily naturalized renditions to increasingly literal ones in terms of both form and content, as Anglophones became more familiar with Japanese history and culture. This new willingness to let premodern Japanese poetry speak for itself, to "make it old," so to speak, developed in concert with stylistic developments in English poetry, which in turn were influenced by Japanese poetry in English. This overview also reveals that the stylistic choices made by Western translators tended increasingly to diverge from those by their Japanese counterparts. While translations from the mid-19 th century to the mid-20 th century receive primary attention here, more recent examples are also selectively considered.