Has anyone ever gotten a free flight upgrade from coach to business or first class? How did you do it?

It happens, but it is very rare. The airlines give free upgrades to their frequent fliers first; usually there's enough of them on any one flight to fill up first/business class. But sometimes, very rarely, there's not. In that case, the coach class would have to be overbooked and some people would either be denied boarding or, if there's space in first/business, they'd be bumped up instead of being bumped off. There is a strict heirarchy of passengers that controls the order that they get bumped up in. They will first upgrade members of their own frequent flyer program who have not earned enough miles to be considered "elite" (for example you need 25,000 miles to reach the Silver elite level which is the lowest, so they would upgrade someone who had only earned 20,000 miles) and for those who have reached Elite level in their partner airlines' programs (like someone who has Gold level on Air Canada might get upgraded on a United flight because they are both in the Star Alliance). If they are still overbooked in coach, they will upgrade based on price paid for the ticket, with the highest fares being upgraded first. So the average traveller who flies a few times a year (or less) and sticks with the cheapest ticket out there has very little chance of being upgraded. The only exception is, if you are scheduled to fly and your flight is overbooked, when the airline asks for volunteers, you can volunteer to give up your seat (which gets you a free flight later on) and ask if you can be rebooked into a first class flight— sometimes that works, sometimes there is not a first class seat available on a later flight.

It used to be that you could show up dressed nicely and give a story about how it was your birthday or anniversary or what-not and sometimes get upgraded but that doesn't happen any more.

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