I always had trouble finding good aviation R/T humor on the net... this threat solved my problem!
As a pilot myself, I have heard of or encounter a few of those amusing moments, and please allow me to shear it with you all.
First two is actually the same controller from Jax Approach, and it happened within 10 minutes while I was flying a 172 from Jacksonville, Florida to Macon, Georgia.
First one:
Comair 123, "Comair 123 checking in FL 250, we have whiskey, looking for a visual runway 7."
Approach, "I wish I have that..."
Second one:
Mooney, "Jax Approach, Mooney...(garbled)...... requesting...(garbled)......"
Approach, "Last aircraft calling, say again callsign. Your transmission is garbled and unreadable."
Mooney(seem frustrated, thus in a louder voice), "Jax Approach, Mooney 12....(garbled).................."
Approach, "Last aircraft calling, speaking louder doesn't make it clearer."
Finally, this is a legend at my flight school, which supposedly happened a few years before I enrolled.
Female Student Pilot, "Craig Ground, Skyhawk 54321 with information charlie, VFR southbound, ready for taxi."
Ground, "Skyhawk 54321, give way to the fokker ahead, taxi to runway 23."
Student, "er... okay... I will taxi to runway 23, give head to the fokker away......"
-Lok