Released mere months after 1960’s gigantic The Button-Down Mind, this chart-topper opens with Newhart remembering his Army experience while making fun of machines taking human jobs—still timely decades later. From there he ponders monkeys typing Shakespeare and how all retirement speeches sound alike, turning surprisingly dark at the end of “Ledge Psychology.” “You should always tie things together,” he notes in his deceptively nebbish-like tone at one point, and somehow the man in the gray flannel suit manages to do just that.