Deep Dark Despair of Sleep is the final Album of the Grass Shadows Trilogy. It is thematising aging and resignation. The album is seeped with the feeling of melancholy coupled with occasional raging against the dying of the light. The melodic ballads show a classic arrangement. Songs like The Deep Dark Despair of Sleep, where the protagonist contemplates alternatives after a relationship or Two Tongues dealing with the ambivalence in a relationship.