A laminated shingle (10) simulates a tiled roof when placed with other similar shingles on a roof deck (D). The laminated shingle includes an overlay member (12) and an underlay member (14) fixedly attached to each other. The overlay member includes an upper or headlap portion (16) and a lower or exposed butt portion (18) with one or more substantially identically shaped tabs (20) with a cutout (22) between each tab. The lower edge (30) of the tabs may have a curving or negative contour. The tabs may taper in width from the butt edge to the lower edge of the headlap portion. The upper edge (28) of the cutouts may have a generally straight contour or a generally curved contour. The lower edge (44) of the underlay member may have a generally straight contour or a portion of the lower edge may have a generally curving contour. The overlay member and/or underlay member may include a darker shading area (36, 48) to enhance the tile simulating aspect of the shingle. In one embodiment, a plurality of shingles may be placed on a roof deck such that the tabs in the course of shingles are vertically aligned with the tabs in the adjacent course of shingles. Alternatively, the tabs may be vertically aligned with the cutouts in the adjacent course of shingles.