During the development of Windows 95 (which released to the public ten years ago today), application compatibility was of course a very high priority. To make sure that coverage was as broad as possible, the development manager for Windows 95 took his pick-up truck, drove down to the local Egghead Software store (back when Egghead still existed), and bought one copy of every single PC program in the store.
He then returned to Microsoft, unloaded all the software onto tables in the cafeteria, and invited every member of the Windows 95 team to come in and take responsibility for up to two programs. The ground rules were that you had to install and run the program, use it like a normal end user, and file a bug against everything that doesn't work right, even the minor stuff. (Of course, you had to provide the program to the person investigating the bug upon request.) In exchange for taking responsibility for ensuring that Windows 95 was compatible with your adopted programs, you got to keep them after Windows 95 shipped. If you did a good job with your two, you could come back for more.
The cafeteria was filled with Windows 95 team members, browsing through the boxes upon boxes of software like bargain-hunters at a flea market. And there were the inevitable "What'd you get?" comparisons afterwards.
I picked up only one program, an English/German automatic translator. It ran fine but produced pretty bad translations. (Not that the quality of the translations was in any way the fault of Windows!)