Three mainstays of modern-day Hollywood discover family legacies that predate the United States itself. Ted Danson learns of two Colonial ancestors who broke the mold: a Connecticut Revolutionary colonel who allowed his slave to buy his freedom, and famed iconoclast Anne Hutchinson, who was banished from Massachusetts Bay for her subversive religious views. William H. Macy learns of his own family's nonconformists — a Puritan punished for helping Quakers who went on to help purchase Nantucket, and a Confederate widow who committed pension fraud to attempt to regain the family's financial stability. Mary Steenburgen's ancestors, too, refused to follow the script, including a rowdy drunkard who served under George Washington in the French and Indian War, and a Tennessee soldier who paid the price of siding with the Union. Taken together, these diverse stories from the past show our guests how personal choices can change history.