Capitalism (PC, 1995)
Making money was never easier than in this stock market simulation game (that predated the tech bubble by several years). Capitalism allowed you to set up your own operations, and forced you to use your business savvy and acumen to perform hostile takeovers and corner markets in order to snuff out potential competition. And, when you eventually went bankrupt, getting back in the game was as simple as clicking the restart button. Bernie Madoff would be proud.