I had a drunk female patient at work one night who was belligerent, treating the staff like s**t, etc. I informed her we are merely trying to help her. She screams at me "do you know who I am?! My husband has a bridge named after him!" I calmly reply, "ma'am if I were married to you, I'd jump off that bridge." This was the only time in my multi decade healthcare career that I was written up. The CEO of the entire hospital system consisting of facilities in multiple states personally called me and laughed about the whole thing...... specifically stating he's golfed with the husband and the husband hates her.

Used to argue with a woman at my job. She cursed like a sailor, this place had no HR department to speak of. One time we were going at it over some protocol and she got so pissed she yells "BITE ME!"

Not skipping a beat I replied, "I don't eat pork.".

That gamer girl that told a dude getting on her "I'm gonna f**k your dad and get pregnant so I can give him a son he'll love" (paraphrasing obviously).

I came back from the barbers and said to my daughter (12 at the time).

"Daddy looks good, doesn't he?"

She barely glanced at me before saying

"You look like something I drew with my left hand.".

I told my wife, jokingly, "You're not the dumbest b***h who ever lived but you better hope she doesn't die."

Without missing a beat, my wife said, "Don't worry, I'd remarry.".

Bessie Braddock MP to Winston Churchill "sir, if I were married to you, I would put poison in your coffee "

Winston Churchill "Madame, if I were married to you, I would drink it".

During a teenage fight with my brother, I repeated what I thought was an iconic line:
"Did you roll off the changing table as a baby?!?!"

Before he could answer, our mom replied, guilt ridden, from the other room:

"THAT ONLY HAPPENED TWICE!".