Lee’s “white teeth and winning smile were irresistible,” according to an officer who served with him, writes Roy E. Blount Jr. in his 2003 literary portrait Robert E. Lee: A Life (Penguin Lives Biographies). And as a young man, Blount writes, one of Lee’s friends said that he could make his friends “laugh very heartily” as he laughed “until tears ran down his face.” Another report comes from after the Civil War, when Lee, upon receiving in the mail a gift of an afghan and tea cozy (cloth for draping over a teapot to keep its contents warm), wrapped the afghan around his shoulders, placed the cozy on his head, and danced to a tune a his daughter was playing on the piano.
Even as a general during the war, Lee was a great jokester who was inclined to pull your leg if you weren’t careful. For example, Blount relays the story of the winter morning in 1862 when Lee’s staff noticed that the general had received a “demijohn,” which is a large-necked bottle, usually inside a wicker cage. Even though his staff members knew Lee to be a near-teetotaler, their imaginations – no doubt based in large part on their experience in which alcoholic drinks were usually contained in such vessels – brought great anticipation. After all, the general was known to share many of the delicacies he received. And sure enough, as lunchtime approached, Lee came out from his tent and said, as reported by Blount, “Perhaps you gentlemen would like a glass of something?” His staff, mouths watering with expectation and cups at the ready, gathered eagerly in the mess tent.
As the demijohn was tipped, out came not wine or a spirit, but Lee’s favorite drink -- buttermilk – to his staff’s great dismay. “His near-teetotaler’s amusement was greater than theirs,” Blount writes.