2. Letterman Returns From Heart Surgery (February 21, 2000)
Dave had long feared that the heart problems that plagued his father — he died of a heart attack at 57 — would claim him as well. At 52, Letterman faced that terror head-on when he went in for quintuple-bypass surgery, which meant taking a break from the Late Show for more than a month. When he returned for his first night back, he made plenty of jokes about his situation, but it was also evident how much the experience had affected him. With typical Letterman-esque flourish, he cheekily brought out the medical team that operated on him, but his usual bite melted away when he told his studio audience, "It was five weeks ago today that these men and women saved my life." Hearing himself say those words, Dave got teary-eyed, a rare, touching sign of the smart aleck's charming vulnerability.