9. "The Jet Set" (Season 2, Episode 11)
Don takes the California trip of his dreams, meeting a mysterious group of exiled European aristocrats who whisk him off to Palm Springs. Naturally, he breezes into their scene without even trying — they can't resist the sight of him sunbathing in his suit and hat. ("You look so comfortable alone by the pool all day.") And back on the East Coast, Peggy misses a Bob Dylan concert to get a haircut from her first gay boyfriend.
Best line: "My father will take care of you. He likes having you around. You're beautiful and you don't talk too much."—Joy to Don Draper