There's a new movie coming out at the end of this month, about the MIT Blackjack Team. Check out the trailer for 21.
The movie concerns a team of MIT students who learn basic strategy, card counting, money management, and other techniques that allow them to develop an edge when playing blackjack. The team was a reformation the original MIT Blackjack Team from the 1970's, but with the new '90s version being run as a business called Strategic Investments. The movie is largely based on the book Bringing Down the House: The Inside Story of Six MIT Students Who Took Vegas for Millions, by Ben Mezrich (whose character becomes Ben Campbell in the movie).
Documentaries have been made about the team, including a BBC documentary called Making Millions The Easy Way. The program itself isn't available online, but the BBC has provided an excellent program summary, question and answer column, and even a complete transcript of the documentary.
The History Channel's documentary on the topic was called Breaking Vegas, which was popular enough to be developed into a short series about people who tried to beat the casinos (both legitimately and otherwise). This special is shown here (complete with commercials):
From the look of the movie trailer and the official site, it looks like it's going to be a stylized version of the story, but adding some drama to it should be good for the storytelling. I like this kind of story not just because of the mathematical hero, but also the basic little-guy-vs.-big-guy aspect of the story. It's also a great story of people beating the odds by using their brains, but without the brains coming off as superhuman. As you'll see in the movie, documentaries or book, they still have to face their emotional sides, too.