On guard one night:

AC1: " You there"
pause
AC1: " You there"
pause
AC1 " You there"
AC2 " YOUR ON GAURD"
AC1 " There he is, there's the guard Nazi "

Going into JFK, crossing HOGGS at FL180 is SOP, but the clearance needs to be issued (or, at least it did at the time). AeroMexico was coming in, and we had just checked on the frequency.

NY App: AeroMexico XXX, I thought I told you to cross HOGGS at Flight Level One Eight Oh!

AM Flight, in a strong Spanish accent: Sometimes you make it...sometimes you don't.

Pause.

NY App: Touche.

Another one: I was flying north-south near RDU. The ride was awful--moderate bordering on severe at all altitudes. SWA was coming east bound to RDU, and asked for a ride report.

ATC: Comair, say ride conditions.

Me: S----y. [This was the first time I had openly sworn on the radio.]

ATC: SWA flight XXX, Comair, 20 miles ahead, he says the ride is, and I quote, s----y.

SWA: [laughing]. Roger copy that. [Immediately followed by...] Comair is right. We confirm the ride is s----y.

ATC: It's not so funny now, is it?

This is something of an urban legend, but it happened for real at least once cuz I heard it (Houston Center, West Texas, 2005-ish).

The FO was struggling on the radio (bad english) and getting is butt handed to him by ATC about the altitude. Then the CA keyed the mike, deep voice flawless but slightly accented english, sounded like the most interesting man in the world...."sometimes you make it, sometimes you don't".

But it got better, ATC gave him a phone number...."OK, maybe we'll give you a call next time we're in the states".

center: contact approach 133.4 good day

foreign accent: 123.4 good day

center:negative 133.4

foreign accent that sounded similar to fez: I SAID GOOD DAY!

On a dark moonless night with no significant ground lighting.
FSS: Airmet Sierra active for mountain obscurations along your route of flight.
Us: Good to know.

Later that same night over the middle of the ocean:
ATC: Request PIREP.
Us: It's really dark.

The FMC up linked waypoints on our 737s for random lat/long waypoints appear as WPT01, WPT02, etc. Heard one of our captains reporting to San Francisco Radio, "(Callsign) waypoint 1 0010, FL370, waypoint 2 0035, waypoint 3 next."

A somewhat busy day with Denver Center en-route to Vegas not too long ago....

United xxxx: "Hey Center, you got the score of the world cup?"
Denver: "Thats the last thing on my mind right now"
Other airline over 121.5: "He no like football"
United xxxx over 121.5: "Freakin commi"
Denver over 121.5: "You guys wanna talk crap about me do it on my frequency"

Guess they didn't know that ATC(and pretty much everyone else) listens to guard

The funniest thing i heard over the radio today wasn't the texan 2 that was asked by tower could you give it a little more and the response being we are giving it ALOT more. It wasnt the airplane that decided to fly into dentons airspace(usaviation) when there were 17 aircraft in the pattern and was told by atc to get out so he immediately left the delta and went straight into the bravo. it wasnt even the chinese student at north texas who said instead of saying ready for take off said cleared for departure as if he was the authority in the matter and not the control. What really took the cake was when the indian foreigner told tower we are taxiing to the "parking lot" towers response was do you mean the ramp? and the foreigner in a stressed voice said we uhhhhhhh are taxiing uhhhhh parking lot!!! and tower said you are cleared........5 second pause.............to the "parking lot"...........

I was a F/O flying a A300 JFK to PBI when JFK issued a extremely long rapid fire revised clearance when I called for our clearance. I asked the Captain who was a friend of mine could I kid the controller and he agreed ed. I keyed up and said using my southern accent sir I am from the south and do not fly up here much so you can give that clearance one time nice and slow or I can ask you to repeat it 5 or 6 time your choice. The controller laughing gave it to me nice and slow.

Accidentally called it Seal B*tch instead of Seal Beach one night coming into LAX...gave us a good laugh at the end of a long 5-leg day :D