While maybe not the funniest, this happened recently. We had an IFR flight plan filed but we wanted to takeoff VFR, do a pattern, land, let off the IP, then pick up our clearance. While this sounds simple enough and we do it all the time, it still causes mass hysteria.
Us: What I just said above.
Ground: Uhhhhh, you want to what?
Us: (Repeat what I said above.)
Ground: Standby....long pause....so you wanna do blah, blah?
Us: No, we wanted do (what I said above).
This went back and forth a few times
Ground: So let me get this straight you want to do (what I said above)?
Us: Roger.
Ground: Okay, sorry about that. I just wanted to make sure that our balls were the same.
Us: (Silence)