The first song that country star Jack Ingram ever taught himself to play on guitar was Willie’s #11 country hit from 1976, “I’d Have to Be Crazy.” On this episode, Jack talks about how learning it clued him into the complex simplicity of the best country songs, from which point he goes into the fundamental question—“To smoke, or not to smoke?”—that anyone has to ask themself the first time they get to meet Willie Nelson, and his song selection that time he played an informal, private set for former president George H.W. Bush.