Two days ago while flying just south of SBN, we were under the arrivals to Midway with several other planes:

SB Approach: Cessna 12345, Traffic is 3 o'clock, 5 Miles, 1,000 above you, Boeing 737.
Cessna 12345: Looking for the traffic.

SB Approach: Cessna 12345, Traffic is now 12 o'clock, 1 mile.....er wait, look straight up....
Cessna 12345: Pilot comes back with a "roger that we've got him in sight" but faintly you can hear a someone in the plane yell Holy F'in S*%T!!!

I don't know why I thought it was so funny but I lost it...

We call it punch-drunk

Cuz the last few hundred times I flew it, it was a seminole

In Pit one slow day

Me: "Ground, (Callsign) 1234, with question"
Controller: "TALK TO ME GOOSE!"

A Skylane had a birdstrike on takeoff and returned to the FBO to check it out with no sign of damage.

Skylane: Ground, Skylane 1234 ready to try another departure with no damage.

Ground: To the plane or the bird.

Skylane: The plane's fine but call Colonel Sanders for the bird.

Tonight outta ATL, several aircraft checked on at once. Center went down a pretty long list giving climbing instructions and the occasional roger...when he was done it went something like this:

Center: And anyone I missed go ahead
((Long Pause))
Center: Man, I'm gooooood.
Airtran: Center, Citrus 123 any chance direct Buffalo?
Center: I'm not THAT good.

I don't know if this one was done yet, I'm too lazy to read through it all. But a chinese student is coming in for landing on a solo.

Cessna 1234: Tower, this is Cessna 1234 inbound for landing
Tower: Roger Cessna 1234 cleared to land, verify you have information "Hotel"
Cessna 1234: No Hotel for me, I stay in student housing!
Tower: (Carefully says without trying to laugh) Cleared to land cessna 1234

I love chinese students

Heard this about 4 yrs. ago while departing PHX for CLD:

American 1234: "ABQ center, American 1234 would like to declare a medical emergency."

ABQ center: "American 1234, state the nature of your medical emergency."

American 1234 (Without laughing/totally serious voice): "We have a passenger bleeding from his testicles."

Flight diverted to PHX w/ a passenger bleeding from his balls!

Departure: "Northwest xxxx say airspeed"
Northwest xxx: "250"
Departure: "Just wondering because I show you at 350"
Northwest xxx after a pause then stutters "Well it sure ain't 350"

MIA Ground: Eagle flight 123 follow company seven five to eight right.

Eagle: Copy that, behind AMERICAN seven five to eight right.