In this article, the author goes beyond Supreme Court decisions to investigate the upbringing and personalities of three Supreme Court justices who left their mark on history: Oliver Wendell Holmes, Jr., Thurgood Marshall, and Sandra Day O'Connor. His interviews with their biographers, G. Edward White for Oliver Wendell Holmes Jr., Juan Williams for Thurgood Marshall, and Joan Biskupic for Sandra Day O'Connor, highlight their formative life experiences and offer insights into the factors that distinguish judges whose careers are ground-breaking from others. Supreme Court biographies can offer students new perspectives on American history and politics, and are a great resource for the classroom. This article presents excerpts from three of the eight conversations contained in the interviews. (Contains 5 resources.)