Not quite in foldingwings' league:
Some years ago, Bondage and I were returning from a JMC up in Jockistan. This involved a night trip back from Turnhoos to Norwich St Faith in an AirUK Fokker Friendship...
The first surprise was the scheduled flight time - something like 3 hours. But they told us that this was because we had to land first at Leeds Bradford. Off we went; then, shortly after departure Bondage having peered out of the window announced "Ah - nasty old break, the wheels won't come up..."
The captain explained that this was because the pneumatic system hadn't got enough puff left, but all would be OK once they'd managed to charge it up from whatever pump they had in the thing. After a few minutes battling against its own built-in headwind, the dear old beast surged forward in relief as the landing gear finally retracted.
Then off to LBA. Round and round and round trying to get in, but the fog defeated us and we set off for the nearest available aerodrome to offload the few pax bound for LBA and so we landed at East Midlands sometime later. At this stage the stewardesses looked very pleased; when we asked why, they told us they were now on some minimum overtime payment. "Sounds like 2 G&Ts then, please" quoth I. "Large ones?" "Yes please!". And so, as the wheels came up at EMA 2 very fine G&Ts were served up! As we made our way back we were then entertained by being intercepted by our own F-4s - a predictable event in those days for the 'Norwich Flyer'!
Overall, great entertainment value!