A stretch film sleeve label applicator for separating a stretchable sleeve label from a web of such labels and applying the label to an item, such as a container, is disclosed. The applicator is particularly useful for applying high stretch labels to highly contoured containers. The applicator is configured to receive a series of labels in an elongated, continuous web of flat, 2-ply sleeve labels, open the continuous sleeve of labels, separate an individual label from a next successive label, stretch the label to permit its application to an item to be labeled, such as a container, and apply the label in an accurate and precise location on the container. The applicator comprises three primary components: a label feeding assembly, a label separating assembly and a label stretching assembly. Various embodiments of the label feeding assembly, label separating assembly and label stretching assembly are disclosed.