deansy.exe
One Christmas the IT staff at the Department for Work and Pensions had a Secret Santa. One of the lads, Mark Deans got the latest issue of gentleman’s top shelf magazine Razzle as from his mystery (presumably female; it’s a softcore mag) gifter, and as he opened it to take a peek, someone else, (it might have been me) snapped a glorious trophy of him donning an exaggerated, pervy smirk while peering into it.
I’d been messing about with the Win32 API at the time, wondering how Clippy could exist in a non-rectangular window. The answer was the “region API” which conveniently came with functions for shaping a window to a bitmap.
So I made an EXE that hides in the background for a few minutes, then Mark pops up in business suit and tie, Razzle in hand, his eyes turn red in an act of MS Paint, focus on the pages, then he sinks back down to whence he came.
As you can imagine, it got added to the start menu of almost every machine in the office.
If I ever find the binary I’ll put it here. Pretty sure it’s on an old hard drive somewhere.