HeadToHeadFive by M. Klein is a free portrait dingbat font built from loose, inked caricatures of faces. The drawings shift between profile and frontal views, but share exaggerated noses, small features, irregular contours, and a quick pen-and-ink quality.
An illustrated poster is its most convincing setting, where a head can become the comic focal point rather than ordinary type, and the drawings also suit editorial spots, event graphics, and merchandise. The odd expressions and mismatched facial proportions make it especially apt for satire, offbeat comedy, and character-driven publishing.