We consider the problem of drawing Venn diagrams for which each region’s area is proportional to some weight (e.g., population or percentage) assigned to that region. These area-proportional Venn diagrams have an enhanced ability over traditional Venn diagrams to visually convey information about data sets with interacting characteristics. We develop algorithms for drawing area-proportional Venn diagrams for any population distribution over two characteristics using circles and over three characteristics using rectangles and near-rectangular polygons; modifications of these algorithms are then presented for drawing the more general Euler diagrams. We present results concerning which population distributions can be drawn using specific shapes. A program to aid further investigation of area-proportional Venn diagrams is also described.