Our Air New Zealand Boeing 747 came with an in-flight entertainment system, including movies-on-demand and arcade games. A few rounds into Tetris, I managed to crash the system, complete with the classic Windows "application has performed an illegal operation and will be shut down" message.
I switched to chess, and beat the system on its "difficult" setting in about twenty moves. Apart from its opening book, the system was pathetic--it couldn't spot a simple fork or think more than a few moves ahead. During the rematch, I got it into a somewhat complex situation, likely a forced checkmate in about ten moves. It hung there with an hourglass for a good twenty minutes, then coughed up a dialog box asking me which part of the system it ought to shut down in order to conserve memory. Honestly, some are incapable of accepting defeat.
After I selected the default option, the entire operating system crashed hard into a black screen and began rebooting. Not surprisingly, the boot screen proudly proclaimed Windows CE circa 2004, then began loading up files using the ancient Xmodem serial protocol. Finally, it booted itself back into friendly pictures of New Zealand coastline. I spent the rest of the flight hoping Microsoft hadn't won the bid on the flight controls.