If describing a smile. Crookedly just describes the twisted nature of the line that the smile makes. Wry can also mean twisted, but in the context of a smile (or humour) wry and wryly describe it as being dry humour or mocking humour. If someone says something with a wry smile, you know they are joking, sometimes in a teasing way. So a crooked smile is how it looks ans a wry smile is what it means as well as how it looks.