Episode: "Babylon" (Season 1, Episode 6)
Context: Don Draper is easy to hate, especially in the first season of Mad Men, when you're just getting to know him. He's a steely womanizer, a money-making thing without a soul. Of course, his monologue about nostalgia during the season one finale changes that, but mid-way through the season, you might find yourself thinking, This guy is rotten. But then he dismantles some beatnik with this retort about sleeping on a bed made of money, and you can't help but nod in approval.
One of Don's greatest attributes is his resistance to sentiment outside of the board room, and this is Double D at his cold-hearted best. "How do you sleep?" the punk asks. There's your answer, bruh bruh.