http://en.wikipedia.org/wiki/Wall_Street_Kid
The premise of the game was fairly ludicrous: if you could earn a decent return on a $500,000 loan, you stood to inherit a $600 billion (!) family fortune. But the stock market in the game, while randomized, was pretty innovative for its time. (It's been awhile since I've played it, of course, but I vaguely remember that there was some sort of internally consistent logic behind the stock pricing movements that seemed to be randomly seeded at the start of each game).
As far as I can tell, the entire game revolved around getting rich off of stocks, wining and dining an increasingly high-maintenance trophy wife, and making a series of very conspicuous consumptions (a yacht, a penthouse, and even a castle). But the mini game in GTA V seems very similar.