Despite the long, rich history and widespread use of pencils and paper, the literature of tribology is remarkably devoid of published research on the subject. The present investigation was conducted to investigate the effects of writing core (i.e. “lead”) grade on the wear response and static and kinetic friction coefficients associated with writing on three types of paper: standard 20 lb copier paper, heavier manila cover stock, and Tyvek™, a spunbonded olefin paper product commonly used for mailing envelopes and surgical clothing. Three mechanical pencil core grades (2B, HB, and 2H) were used. These materials varied in Knoop microindentation hardness by a factor of approximately two. Static friction coefficients were determined from simple, inclined-plane tests of the various core-paper combinations, and kinetic friction coefficients were determined by pin-on-disk tests. Against all but the Tyvek™, static friction coefficients were not dependent on core grade or paper type. Kinetic friction coefficients were not clearly correlated with paper type or core grade; however, significant differences in the core wear and paper in-filling characteristics were observed. Scanning electron microscopy and quantitative image analysis were used to study the manner and extent to which the core wear particles were embedded and agglomerated within the tangled fibers of the papers. A clear correlation was observed between the degree of transfer of wear particles to the paper and the hardness of the core in two of the three paper types.