14. "In Care Of" (Season 6, Episode 13)
After a life spent trying to move forward, Don picks a spectacularly bad time to look back on his childhood, falling apart in the middle of his Hershey pitch. His life in ruins, he hits the road with his kids on a long Thanksgiving drive, then decides to pull over in Pennsylvania to show his daughter the whorehouse where he grew up. She raises an eyebrow at him. Then they stand there by the side of the road together, looking like a couple of lost kids, neither one with any idea what to say next.
Best song: Judy Collins' "Both Sides Now," which makes that final shot even more devastating.
Best line: "Well, aren't you lucky to have decisions."—Peggy Olson