Crete is a little provincial, so do not expect the same range of entertainment you would get in a city. Most of the events are based in the towns. Elsewhere, the main entertainment is provided by watching people do their "volta" - literally the "turn". This consist of slowly walking up and down the main street (or other area where people congregate) to see and be seen.
Cinemas in Chania. Films are always shown in original version with Greek subtitles (with the exception of children's films which are often dubbed)
Theatre and plays are sometimes shown in Chania and other cities but almost exclusively in Greek language
Music: there are concerts, especially in the summer, but the main place to listen to Cretan music is at feast such as weddings, baptisms and village feasts.
Traditional Cretan entertainment is almost always related to weddings or baptisms and will involve eating, drinking, listening to traditional music and dancing for most of the night. You can also see tourist versions of these feasts provided by tour operators and which often go by the name of "Cretan evening".