The propagation of light from distant sources through a distribution of clumpy matter, acting as point-mass lenses, produces multiple images that contribute to the total brightness of the observed macroimages. In this paper, we refine the theory of gravitational microlensing for a planar distribution of point masses. In an accompanying paper, we extend the analysis to a three-dimensional lens distribution. In the two-dimensional case, we derive the probability distribution of macroimage magnification, P(A), at A -1 ≫ τ 2 for a low optical depth lens distribution by modeling the illumination pattern as a superposition of the patterns due to individual "point-mass plus weak-shear" lenses. A point-mass lens perturbed by weak shear S produces a...