Context

This line is spoken by Harry Callahan, played by Clint Eastwood, in the film Dirty Harry, directed by Don Siegel (1971).

California cop Harry Callahan is not happy to have his lunch interrupted by a robbery. He shoots the bank robber and his getaway driver, all while finishing a bite of his lunch.

Then he walks up to the wounded robber, whose gun is lying within grabbing distance. Does the guy dare reach for his gun? Harry plays dirty by taunting him, saying, "I know what you're thinking: Did he fire six shots or only five?" In other words, he's saying that his own gun might be empty, but does the criminal want to risk it? Then he utters the big line: "You've got to ask yourself one question: 'Do I feel lucky?' Well, do you, punk?" 

The punk does not feel lucky, even though Harry did, in fact, fire six shots and has an empty gun.

Where you've heard it

You've heard this quote almost any time someone with a gun wants to taunt someone else—in everything from video games (Resistance 3, Lego City Undercover) to TV shows (Last Man Standing, Duck Dynasty) to movies (Fast & Furious). Here's the thing, though: people almost always misquote it as "Do you feel lucky? Well, do you, punk?"

At least Jim Carrey got it right when trying to rescue Cameron Diaz in The Mask.

Additional Notable References:

• Full Throttle
• Transformers: The Movie
• Mass Effect 2
• Mafia II

Pretentious Factor

If you were to drop this quote at a dinner party, would you get an in-unison "awww" or would everyone roll their eyes and never invite you back? Here it is, on a scale of 1-10.

Depends if you try to sound like Dirty Harry while quoting it.