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"Look, we've got oysters rockefeller! Beef Wellington! Napoleons! We leave this lunch alone, it'll take over Europe."
--Season 1, Episode 6: "Babylon"
"I guess what I'm saying is at some point we've all parked in the wrong garage."
--Season 1, Episode 7: "Red in the Face"
"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."
--Season 1, Episode 7: "Red in the Face"
"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.'"
--Season 1, Episode 10: "Long Weekend"
"When God closes a door, he opens a dress."
--Season 1, Episode 10: "Long Weekend"
"I shall be both dog and pony."
--Season 1, Episode 11: "Indian Summer"
"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."
--Season 1, Episode 11: "Indian Summer"
"Can I just fire everyone?"
--Season 2, Episode 2: "Flight 1"
"Don't you love the chase? Sometimes it doesn't work out; those are the stakes. But when it does work out, it's like having that first cigarette: your head gets all dizzy, your heart pounds, your knees go weak. Remember that? Old business is just old business."
--Season 2, Episode 4: "Three Sundays"
"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."
--Season 2, Episode 5: "The New Girl"
"Do you want to be right, or do you want to be married?"
--Season 2, Episode 9: "Six-Month Leave"
"It's easy adjusting to happiness."
--Season 3, Episode 3: "My Old Kentucky Home"
Roger Sterling is a Partner at the Sterling Cooper Draper Pryce advertising agency; his father founded the original Sterling Cooper in the 1920s with Bertram Cooper. A World War II veteran, Roger has suffered two heart attacks. In the past he’s tried to change his hard-living ways, but is now smoking and drinking again.
Roger divorces his first wife, Mona, after taking up with the much younger Jane Siegel, who briefly worked as Don Draper's secretary. Previously, Roger had a lengthy affair with Joan Holloway, then Sterling Cooper’s Office Manager.
Anticipating a costly divorce settlement with Mona, Roger encourages the takeover of Sterling Cooper by London’s Puttnam, Powell, and Lowe. When the new managers leave him off a corporate organizational chart, however, Roger believes he’s "being punished for making my job look easy." He feels similarly slighted by friends who can’t accept his relationship with Jane. "I made a mistake by being conspicuously happy," he tells Don.