Rachel Menken: It's hard to get caught in a lie.
Don Draper: It wasn't a lie, it was ineptitude with insufficient cover.

Roger Sterling: [about Bethany Van Nuys] You hit it off, come Turkey Day, maybe you can stuff her.

Roger Sterling: [about Miss Blankenship] She died like she lived, surrounded by the people she answered phones for.

Roger Sterling: [after suffering a heart attack] All these years I thought it would be the ulcer. I did everything they told me, I drank the cream, ate the butter. Then I get hit with a coronary.

Roger Sterling: [as they leave their old offices] How long do you think it'll take us to be in a place like this again? :Don Draper: I never saw myself working in a place like this.

Roger Sterling: [to Don, about making a pass at Betty] At some point, we've all parked in the wrong garage.

Roger Sterling: I bet daily friendship with that bottle attracts more people to advertising than any salary you can dream of.
Don Draper: It's the way I got in.
Roger Sterling: So enjoy it.
Don Draper: I'm doin' my best here.
Roger Sterling: No, you're not. You don't know how to drink. Your whole generation, you drink for the wrong reasons. My generation, we drink because it's good, because it feels better than unbuttoning your collar, because we deserve it. We drink because it's what men do.
Don Draper: What about shaky hands, I see a lot of that with you boys?
Roger Sterling: No joke. Your kind with your gloomy thoughts and your worries, you're all busy licking some imaginary wound.
Don Draper: Not all imaginary.
Roger Sterling: Yeah, boo hoo.
Don Draper: Maybe I'm not as comfortable being powerless as you are.

Roger Sterling: I bet there were people in the Bible walking around, complaining about "kids today."
Don Draper: Kids today, they have no one to look up to. 'Cause they're looking up to us.

Roger Sterling: I love how they sit there like a couple of choirboys. You know one of them's leaving New York with VD.

Roger Sterling: I watched the sunrise today. Couldn't sleep.
Don Draper: How was it?
Roger Sterling: Average.

Roger Sterling: It's a mistake to be conspicuously happy.
Don Draper: No one thinks you're happy. They think you're foolish.

Roger Sterling: Look, I want to tell you something because you're very dear to me and I hope you understand it comes from the bottom of my damaged, damaged heart. You are the finest piece of ass I ever had and I don't care who knows it. I am so glad I got to roam those hillsides.
Joan Holloway: Stop it.

Roger Sterling: Peggy, can you get me some coffee?
Peggy Olson: No.
Season Four

Roger Sterling: Psychiatry is just this year's candy pink stove.

Roger Sterling: Remember, Don...when God closes a door, he opens a dress.