I like to think that longtime readers have picked up on my love for all things markets. I also love the movies and in honor of the Oscars last night, I thought that it would be fun to list the best (and worst) Wall Street movies of all time.

To make this list even more fun, I’ve included links to trailers and clips, but I have to warn you about two things.  First, there are often advertisements before the clips and, secondly, a lot of the clips have profanity.

Let me start with a few honorable mentions.

Although I wouldn’t characterize American Psycho as a Wall Street movie per se, the lead character, Patrick Batement, played by Christian Bale, is a stereotypical 1980s soulless investment banker. Although the movie is a black comedy, it’s also a gruesome horror movie.  I have mixed feelings about the movie, but I’m including it on the list because of a brilliant scene where a bunch of bankers play a game one-upmanship over business cards.  Click here for the clip; this scene includes profanity.

Speaking of profanity, one Wall Street movie that I didn’t like was The Wolf of Wall Street, directed by Martin Scorsese and featuring Leonardo di Caprio.  It also features the ‘f’ word 567 times in 180 minutes – the third most of all movies (and second place is a documentary about the ‘f’ word).  This movie is about a bunch of lousy brokers that cold call unsuspecting people and browbeat them into buy penny stocks. Unfortunately, it’s based on a true story. Here’s a clip of some of the cold calling; this scene includes profanity.

This was also the basic storyline of Boiler Room, which is another term for bucket shop.  It’s only a so-so movie, but there is one scene where all of the bad brokers go to an empty mansion in the suburbs of New York in their fancy cars and watch the movie Wall Street.  I once knew a guy who had worked at a boiler room in New Jersey and he told me that this was the most realistic thing that he’d ever seen in any movie ever.  Here’s the clip, which, not surprisingly, includes profanity.

Like American Pyscho, this next movie isn’t great, but it does include an important scene that really describes bond trading from the dealer’s perspective.  The movie, Bonfire of the Vanities, was based on a novel by the same name by Tom Wolfe.  This wonderful book didn’t translate well onto the big screen, partly because no one could believe Tom Hanks as a serious actor. In this scene, he and his wife (who are having problems) are trying to tell his daughter what daddy does for a living.  It’s so much better in the book, but it still works on screen.  Here’s the clip, and, for once, there is no profanity.

A few more honorable mentions include Arbitrage, which is kind of a rip off of Bonfire), Rogue Trader and Barbarians at the Gate.  Interestingly, the latter two are based on real stories.  Rouge Trader features the story of Nick Leeson, the currency trader that broke Barings Bank.  Barbarians is the story of the battle to buy RJR Nabisco.

Now, for the moment you’ve been waiting for – the best five Wall Street movies of all time!

Number Five: Margin Call

Margin Call is essentially a fictional treatment of the 2008 financial crisis.  A bunch of risk managers discover that their bank is about to go under, they tell senior management, who decides to screw their clients to stay in business.  It’s a troubling movie because it’s so right on the money.  Here’s the trailer.

The Big Short is also about the 2008 financial crisis, based on the book of the same name by Michael Lewis.  This story follows a few traders that saw the meltdown coming and profited handsomely.  There are a lot of great scenes in this movie, but my favorite scene uses the game Jenga to explain mortgage bonds.  Here’s the clip, and, yes, there’s profanity.  The portrayal of this banker in this scene is hilarious because he’s such a jerk and it’s so believable.

The only thing that I didn’t like about this movie is that Brad Pitt so blatantly stole my look and didn’t compensate me for it.

Number Three: Other People’s Money

This gem from 1991 stars Danny DeVito as Larry the Liquidator, a corporate raider that targets a small town cable company run by all around good guy, Gregory Peck.  The movie is excellent in so many ways, but I particularly like this scene where DeVito eloquently explains value investing.  It’s so brilliant and DeVito is awesome, but is crude and has profanity.  I didn’t remember this, but he refers to his talking computer, Carmen, long before any of us had contemplated Siri or Alexa.

Number Two: Trading Places

This is one of the funniest movies of all time, featuring Eddie Murphy and Dan Aykroyd.  Two rich brothers, Randolph and Mortimer Duke, are trying to answer the age old ‘nature versus nurture’ debate and bet that they can take a street hustler, Murphy, and turn him into a star trader.  At the same time, they strip everything from their employee, Aykroyd, to see if he can survive.  The movie is awesome and the climax takes place on the trading floor of one of the Chicago exchanges, which you can see at the end of the trailer.  This movie actually inspired two successful traders to try this in real life and the ‘turtle traders’ were born (more on that here).

Best Picture: Wall Street

It should come as no surprise that the greatest Wall Street movie of all time is Wall Street, directed by Oliver Stone and starring Michael Douglass in the role that defined his career.  Instead of summarizing the film, I’m attaching the trailer and the most famous scene where Gordon Gekko boldly states that ‘Greed is good.’  Amazingly, Oliver Stone didn’t write the line, but instead took it from a speech by arbitrager (and convicted insider trader) Ivan Boesky at a 1986 graduation address at Berkeley.  Be sure to avoid Wall Street 2: Money Never Sleeps, it’s awful in every way.

I hope you’ve enjoyed this list – if I’ve forgotten any great movies or scenes, let me know.  I have to admit that as I wrote this up, I was struck by how awful Wall Street can be from the boiler room brokers to ‘greed is good.’  As I said at the top, I love securities and markets, but now realize that I’m happy to be doing it as a fiduciary in suburban St. Louis.