1992 -- vacation in Florida -- first time flying without my parents. We were in Miami flying to NY on AA. Aircraft was downgraded from something that sat 300+ people to something that sat 150 people (I forget the aircraft types). We volunteered for $500 each and a seat on a plane 2 hours later. We also asked and received food vouchers.
We sat at the bar and had a great time. Ended up that the origial flight had engine problems, had to return to the gate, they would not let the passengers off the plane, and took off 15 minutes before our flight. $500 for 15 minutes -- I'll take that anytime!
Worst tease -- twp months ago flying from NY to ORD. American was overbooked and needed volunteer. I volunteered but was told they would not need me. I boarded the plane (was upgraded) and stowed my bag. Gate agent comes on the plane and signals to me that she needed my seat. Get bags, leave plane. I no sooner make it off the plane then she tells made a mistake and did not need my seat. Get back on the plane (still had the upgraded seat) but no space for my carry-on -- the last passenger who got on took my space. They made me check my bag -- which delayed me getting to my hotel in PHX!
Oh well -- sometimes you win and sometimes you loose!