(to Lisa) Seymour Skinner never puts all his eggs in one basket. That's why they call me "Two Basket Skinner." (pause) What? They do.

Principal Skinner: Martin Prince was known by many names. Martin Priss, Martin Princess, Fartsin Prince, Martin the Brown-Nose Reindeer...
Dolph: That was mine.

Superintendent Chalmers: We're gonna put Bart Simpson away for a long, long time.
Principal Skinner: By law, the most we can give him is a 10-day suspension.
Superintendent Chalmers: That's long to a kid.

(After the Diet Coke and Mentos explosion.)
Superintendent Chalmers: Skinner! (Pause) Skinner?
Principal Skinner: I'm alright, sir.
Superintendent Chalmers: Don't ever scare me like that again.

Nelson: (to Washington Post reporter) Haw-haw! Your medium is dying!
Principal Skinner: Nelson!
Nelson: But it is.
Principal Skinner: There's being right and there's being nice.

(In "Mr. & Mrs. Simpson" Homer and Marge both shoot Principal Skinner.)
Principal Skinner: (Dying) Remember me... on pizza... Fridays.
Homer: No!

Superintendent Chalmers: I'm a bit of a crossword head myself. They help me relax after a day of having to deal with... Skinner!
Principal Skinner: You called?
Superintendent Chalmers: Made reference.
Principal Skinner: My mistake.

Principal Skinner: I can't believe I'm out of gas. I put in one dollar of gas and I've only driven ninety cents.
Agnes Skinner: You had to drive with the windows open, didn't you, Rockefeller?

(Principal Skinner treats Superintendent Chalmers to dinner at his home.)
Superintendent Chalmers: Seymour, those string beans were cooked to perfection. After 20 years, I am finally starting to like you.
Principal Skinner: Just wait for dessert, sir. I made it with you in mind.
Superintendent Chalmers: Outstanding. I'll just shut my eyes and let you place it before me.
(Selma's erotic cake accidentally flies in through the window and lands on the table in front of Chalmers and Skinner and the two recoil in horror when they see it.)
Agnes: (from upstairs) Seymour! What's going on? I'm coming down there!
Superintendent Chalmers: Quick! We'll have to eat from each end. We'll know we're safe when our lips meet in the middle.

Principal Skinner: You yell at me for everything.
Superintendent Chalmers: Well I cant yell at anyone else. Teachers have unions. Students have parents.
Principal Skinner: What about Willie?
Superintendent Chalmers: I like Willie.

Lisa, one of the hardest jobs I have is throwing cold water on young children's dreams. Ralph, you're not a kangaroo.

Buying trophies from those cash-strapped schools really filled out the case.

The Simpsons Quotes

Marge: Tomorrow night, it might be nice to go out for dinner.
Homer: Tomorrow night? Friday? Pork chop night? Marge! We haven't missed pork chop night since the great pig scare in '87!

Wow, now I see why they call you Miss Hoover. You must have been vacuuming for an hour.

Bart