This would be more along the lines of "The Silliest Raises Our Sims Have Gotten," but I once had a sim in a custom career that, by design, paid a negative wage for the first three levels or so. Meaning the sim was actually paying a few simoleons an hour for the privilege of working there. The benefits, such as they were, for being in that career came later on.
And somewhere along the line at least a couple of times at the lower levels my hardworking always punctual sim got a wonderful announcement of a -§2 raise (sure, negative wages will kick up negative raises as it's done by percentages). Whoopdie-doo, happy days are here again. :/ :p
