In October 2006, Supreme Court Justice Sandra Day O'Connor sat for two 3-hour sessions, agreeing to have her portrait painted by not one, but 25 separate artists. In the end, these painters - some amateurs, some professionals - created vastly different images of this iconic figure, shedding light on both their subject (who entertained the room with anecdotes about herself and other Supreme Court luminaries), as well as the process and heritage of portraiture in American history and politics.