A labeling head (22) has an applicator surface (24) having an outward curvature for holding a label (12) and applying it to a labeling surface (16) of an article (14). The labeling head is rotatable about a pivot pin (38) which passes through a pivot end (28) of the labeling head, allowing a free end (26) of the labeling head to be biased toward the article at an initial angle of bias, as determined by, for example, an adjustment screw (40). The initial angle of bias and the curvature of the labeling head are such that the portion of the label nearest the free end is parallel to the labeling surface. As the labeling head is lowered, the label is applied with a substantial rolling motion to avoid trapped air bubbles.