My first time at ORD I'm in the left seat. Finally work my way up to #2 when ATC calls:
ATC: Candler ###, got a reroute, ready to copy?
FO after I nod: Candler ###, afirmative.
ATC: (I don't remember the exact details, and I have not been there in years, but something like this) Turn left on F, cross 27L, right on the outer loop, left on A21, left on P, right on H, hold short 32R, understand you are ready to copy your re-route?
FO after we exchange puzzeled looks: Ahh, we thought that was our re-route.

The other day we were flying approaches into SBN in the 172, we had a Hawker behind us so the controller told us to maintain best forward speed on the approach. Well it was kinda bumpy throughout the approach and just as we were touching down the tower asked the Hawker what his ride was like. The female first officer came on and said that there was some light chop. A half second later the captain (male voice) attributed the bumps to "the wake turbulence of the Cessna"
I found it kinda funny when tower asked us how our ride was. we had some bumps and I said "some light turbulence on final but of course everything bumps us around."
When the captain comes back on and declares that the bumps we felt were "the bow wave off the hawker"

I flew T-34s out of NAS Pensacola, home of the Blue Angels. Obviously, the T-34 bubbas were treated like stepkids when the Blues were in town. I was getting ready to takeoff #2 behind a Blue Angel departing for some exotic location. The exchange went something like this:

BA: Tower, Blue Angel 7 ready for takeoff, request unrestricted climb to 370

Twr: BA7 cleared for takeoff and unrestricted climb to 370

As the BA starts rolling, I call for takeoff.

T-34: Tower, Wildcat xxx ready for takeoff, request unrestricted climb to 800 (our pattern altitude)

BA7: Oh, funny guy (at least he had some sense of humor)

Stetson20

Another one from my Cobra days. A pilot and a controller get into a little pi$$ing contest on the radio, with about a dozen Cobras in the pattern. The pilot finally tells the controller "Listen partner, you fly that mic of yours and I'll fly my airplane."

Another controller came on the frequency to continue operations.

Years ago in my light twin days, a frentic female controller at MEM center gave a NWA DC-9 an extremely tight crossing restriction "Northwest XXX cross XXX at 10000'." The captain calmly replies "We're not a rock, we can't do that!"

I copy your transaction!!!

A few years ago (2002) during one of my many routine departures out of Kuwait Int (OKBK) we were told to expect to hold at xyz intersection waiting crossing clearance into Saudi. We responded, "We really don't want to do that, what seems to be the problem?" The Kuwaiti controller responded that the Kingdom of Saudi Arabia was having a problem with our diplomatic clearance. We responded with, "Well it's on our flight plan and we would like to continue and work it out without holding, when your ready to copy we can pass the approved dip clearance for Saudi Arabia." We smugly passed the info and grinned at each other and mentioned to ourselves on how slick we were working the issue so quickly. A few minutes passed, and then as we were rapidly approaching the holding point the controller raised an octave in his voice and said, "Duke XX, the Air Defense of the Kingdom of Saudi Arabia says you should not cross their border, hold as requested!" We quickly responded with, "Roger! Duke XX entering holding now on the Kuwait side of the border." After a few moments of silence, we got several comments from other aircraft like "whoa partner", "hehe that didn't go so well" and the like. It seemed that our call sign and our dip clearance had been changed without our knowledge…..it all worked out after a return trip to Kuwait Intl to re-file, but this little incident sure gave us a wake up call as to expecting "routine" flights.

A couple years ago I was with a student on our way to SNS. As requested, my student reported the 5-mile final. What came back was pretty much a muffled, garbled mess. We both looked at each other, neither understanding what Twr had said. Student says "say again", same result. I get on the horn and say "Sir, we're sorry but we can't understand a word you're saying". A few seconds pass, and Twr gets back on and says "Sorry guys, I had a mouthful of chicken". That was good for a few laughs.

I had a nice one in Kuwait. About 06:30 droning along thinking about the hot breakfast coming up, what my wife and I will do when I get home...when I hear, "Aircraft squawking ####, this is Kuwait Air Defense on guard, identify yourself immediately or you will be fired upon." Well, we're talking with Kuwait approach, we've got the correct IFF, so I think nothing of it until the crew chief says, "Hey sir, I think that's our squawk." Look down, spill my coffee, holy #$% that IS us. We jumped on guard and told Kuwaiti AD who we were... no reply. Tried a few more times, no luck. Tried to explain to Kuwait approach what had just happened... got the old "Roger". I'm here to write about it, so I guess some one figured it out. We did not laugh about it at the time, but we sure did later on. Kind of.

"Uhh..Kent State unicom, Cessna Nxxxx clear of the active taxiing to the fuel pumps for fuel and a window washing."

"Uhh..Kent State traffic, Cessna Nxxxx departing runway 19 east turn out IFR to Chicago"