Picking the 5 best Roger Sterling quotes is actually fairly difficult because he produces so many fantastic quotes. The character Roger Sterling on the hit show “Mad Men” is the kind of guy that’s both flawed and wise. He’s smart enough to know his own foibles, but he’s generally accepted them, and he has no intention of changing anytime soon. The best Roger Sterling quotes often reflect a wry sort of pessimism that permeates his whole character.
- In season 1 episode 4, Roger Sterling uttered the following to a younger co-worker, “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.” Out of all the Roger Sterling quotes, this one does the best job reflecting Roger’s tendency to become irritated with others who don’t see the world the same way he does.
- In season 1 episode 10, Roger said, “You know what my father used to say? Being with a client is like being in a marriage. Sometimes you get into it for the wrong reasons, and eventually, they hit you in the face.” This is one of the better example among the Roger Sterling quotes of his fatalism about success in business. He considers himself a lucky man, and he doesn’t necessarily expect his success to last forever.
- In season 1 episode 7, after demonstrating some bad behavior Roger said, "When a man gets to a point in his life when his name's on the building, he can get an unnatural sense of entitlement." This is one of the best Roger Sterling quotes when it comes to showing his awareness of his own weaknesses. Roger knows that he’s far from a perfect person, and he isn’t ashamed to admit it.
- Roger often has a wry sense of humor about relationships, and he’s no fan of the concept of marriage. In season 2 episode 5, Roger said, "I'll tell you the same thing I told my daughter: if you put a penny in a jar every time you make love in the first year of marriage, and then you take a penny out of the jar every time you make love in the second year, you know what you have? A jar full of pennies."
- Finally, to finish of this list of the best Roger Sterling quotes, we’ll include another example of Roger’s general dislike of marriage. In season 2 episode 9, Roger said, "Do you want to be right, or do you want to be married?" This one is shorter than most of the other Roger Sterling quotes, but it does a good job capturing his general attitude about most things.