Wall Street (1987)
Before he was making millions of dollars per episode on Two and a Half Men, and way before he ever claimed he had “tiger blood” running through his veins, Charlie Sheen had an impressive repertoire of films on his CV. One of these was arguably one of the most famous films on this list: Wall Street.
This film is a classic portrayal of a man that is a master of his craft (Gordon Gekko, played by Michael Douglas), and in this case, the craft being the business of the stock market. Gekko is a millionaire stock-market manipulator and extraordinaire whose thirst for money drives him into ever more illicit dealings in the stock market. He takes a young, naïve hopeful Bud Fox (played by Charlie Sheen) under his wing, with Fox discovering just how dark and sordid Wall Street can possibly be.
The film is really a classic morality tale at its core, where in the context of finances, the film makes one question when “enough” really is enough. The relationship between the ruthless Gekko and the initially-ambitious and unexperienced Fox is interesting enough, and though no new moral tales are explored in any depth here, it is a dramatic and thrilling peek into the windows of the offices boardrooms where serious stock market happenings take place, and Oliver Stone’s directing coupled with Douglas’ acting makes this a gritty, if somewhat predictable wall-street tale.
If Wall Street is the glitzy, polished depiction of the high end of the stock-market world from Hollywood, then the kind of trading taking place in Floored is much closer to the real-life world of stock and futures trading. This is no glossy depiction of boardrooms in the sky, however: Floored is a documentary that takes the viewer on a small journey into the world of futures trading, and is set in Chicago. The focus is on floor traders going about their daily jobs, which is somewhat of a relic if you’re watching in 2018 since most trading is now done via the internet.
If you’re expecting a truly unique take on the stocks or futures trading world, you likely won’t find it in Floored. However, it does do a good job of depicting some of the tremendous highs and potentially catastrophic lows that the stock market can produce for people caught up in its dizzying ether. It is also a great example of looking back at the impact that technological revolution can and did have on the trading world.
Wolf of Wall Street (2013)
If you didn’t know who Jordan Belfort was before watching The Wolf of Wall Street, you certainly did once the credits came rolling up. This is one of the most critically-acclaimed films on the list, with a dazzling cast ranging from a subline Leonardo DiCaprio to Jonah Hill and directed by none other than Martin Scorcese himself.
This film a 3-hour epic that feels like it barely lasts a single hour thanks to the fast pace, unbelievably good script, terrific acting, and some excellent comedic scenes (including that scene with DiCaprio high on Quaaludes trying to open the door of a sports car).
This film specifically focuses on Jordan Belfort’s perspective and is based on his autobiography. It tells his tale of making his dishonest fortune by trading on penny stocks, hilariously yet artfully setting a swift pace that intrigues the viewer from beginning to end. Depictions of the trading floor, the high life (in every manner of the word), as well as his eventual arrest, incarceration, and beyond can all be found in this movie, which is arguably one of the most impressive in this list overall.
Margin Call (2011)
Perhaps a contentious title for many thanks to it starring the now-disgraced Kevin Spacey, Margin Call follows the story of key employees of an investment bank before and during the 2008 financial crisis. The film was nominated for an Oscar, as well as winning many awards; it was also praised by many critics for its impressive acting, smart storytelling, and excellent delivery of an interesting subject.
The film concentrates on a 24-hour period during the time of the 2007-2008 financial crisis, and has central themes running through it that one would expect of a film about stock trading: greed, capitalism, and of course, illegal dealings such as investment fraud. This is arguably one of the best films about wall street made in the last decade, if not ever, in fact. It deals extremely well and with a high degree of accuracy the inside workings of investment banking (with the obvious Hollywood shine added for dramatic effect, of course). The film doesn’t specifically name the firm contained within, but it is most likely a hint at Goldman Sachs, given the similarities between the mortgage-backed securities dealings that take place within the film.
Trader is arguably one of the most accurate insights into the everyday happenings of wall street. This is a one-hour documentary that offers a fascinating insight into the trading world, filmed before the famous 1987 Stock Market Crash (also known as Black Monday).
The documentary follows Paul Tudor Jones II, and brings the viewer up close and personal to the actual ins and outs of futures trading, as well as into the life that his profession afforded him. Even scarier is the words of Paul Tudor Jones echoing the actual crash that followed not long after the film was made. In it, he posited that America was nearing the end of a 200-year bull market, a prediction that rang eerily true considering the crash in 1987.
Wall Street: Money Never Sleeps (2010)
Though this film didn’t receive the critical acclaim of the original, this sequel to Wall Street was directed by Oliver Stone, starring Michael Douglas and Shia LeBeouf. It is set 23 years after the original, this time having its focus squarely on the financial crisis of 2008.
The events follow a predictable course, with Gordon Gekko being released from prison and attempting to mend his relationship with his daughter. However, expect to see Gekko’s love for money take over as he dreams up a modern-day plot to commit even more illegal stock-market activity. The overarching theme of this film feels like it should be that excessive greed is a bad thing, however we never actually see any catastrophic consequences to the actions of the films’ main characters, despite the film being set around the time of one of the worst financial crises the world has ever seen.