13. "Far Away Places" (Season 5, Episode 6)
We all knew the "somebody tries LSD" episode was coming, and we all knew the "Roger and Jane break up" episode was coming — but combining them was a typically brilliant Matthew Weiner curveball. While Roger swallows the sugarcube, Don and Megan take a different journey to Howard Johnsons, where the sherbet turns out to be a bad trip. Don hallucinates he's back on vacation in Disney's Tomorrowland, in the days when a milkshake was just a milkshake. And this whole episode gets even more psychedelic when you watch it synched up to Pink Floyd's Dark Side of the Moon.
Best song: The Beach Boys' "I Just Wasn't Made For These Times," a poignant soundtrack to Roger's acid trip. This is his happening and it freaks him out.
Best line: "I knew we were going someplace, and I didn't want it to be here."—Jane Siegel Sterling