A web of roofing material (20) is perforated for segmentation into plural trapezoidal-shaped shingles (22). In view of the perforation (24) of the web (20), the trapezoidal-shaped shingles (22) are pre-configured for use as hip and ridge shingles advantageously having edges pre-shaped to align upon installation to present an essentially straight line of edges of contiguous shingles. The hip and ridge shingles are detachable from the web at the perforation to facilitate use of the shingles on a roofing obliquity (40). A method of applying shingles to a roof includes segmenting a pre-perforated web of roofing material into individual shingles, positioning a first trapezoidal shaped shingle on the roofing obliquity (40) so that the major parallel edge thereof is bent across a bend line of the roofing obliquity and so that the major parallel edge of the first trapezoidal shaped shingle serves as a leading exposed edge of the shingle, affixing the first trapezoidal shape shingle to the roof understructure, and using a sealant strip (36) of the first shingle as a guide for positioning a second shingle over the first shingle. A method of making the roofing material comprises forming a covering material on a first surface of a substrate; cutting the substrate into a web, the web comprising plural trapezoidal shaped shingles; and, forming perforations in the web to facilitate segmentation of the web into the plural trapezoidal shaped shingles.