Best Finance Movies About Trading & Investing Reviewed

Trading makes great movies because the stakes are so high, in some cases, the entire World is at risk of being bankrupted. In others, it’s just plain stealing, scamming, lying and greed. This is fine if it’s make-believe and escapism, but not so fine if it’s real life. Here, I review some of the best films about Wall Street, trading and investing. Some of which are alarmingly based on real life…

Trading Places (1983)

John Landis cannot be beaten here. Sterling performances from Eddie Murphy, Dan Aykroyd, Jamie Lee Curtis, Don Ameche, Ralph Bellamy and Denhold Elliot make it not just one of the best movies about trading, but one of the best films ever made. However, you could say that it has not aged well, as I recently rewatched it to film a video explaining how it ended.

An excellent satire on greed, insider trading and how the brokerage industry actually works. Many of the scenes filmed on location in New York Exchanges are very realistic, with lots of real traders used as extras.

Wall Street (1988)

Oliver Stone captured New York perfectly in Wall Street, from Sinatra’s “Fly Me to the Moon” in the opening credits, to “Greed is Good”, to the salesmanship of stock brokers trying to land whales, or “bag an elephant”. It’s another tale of how insider trading and taking shortcuts will get you unstuck in the end.

The irony, of course, is that insider trading is still a regular occurrence and works pretty much in the same way as the film depicted. Which is leaky lawyers, tell their broker mates what deals are in the works down the pub, who then tip off their clients, who then place massive trades, and the broker take a bit more commission.

Rogue Trader (1999)

This was one of the first DVDs I ever owned, and along with Trading Places, it was my inspiration for getting my first job on the NYMEX trading floor in New York. Peak Ewan McGregor playing Nick Leeson, who was an excellent example of the types of traders you would see in the pit.

Shockingly, even though he brought down Barings Bank by hiding loss-making trades in their “error account” even to this day, I don’t think the industry has learnt its lesson, and there are still no proper risk management tools in place at prime brokers.

When I was a broker, for example, we had no limits on our house trading account, and errors were generally not picked up until the “check off” the next day. And look what happened to MF Global. If you don’t know, you can read about it in The Money Noose.

Leeson himself even complains about how banks are “too scared” to hire him for in-house consultancy, even though he quite often does after-dinner speaking at banking events.

Boiler Room (2000)

Vin Diesel and Giovanni Ribisi’s finest rolls, with an “Act As If” Glengarry Glen Ross-esque scene steal from Ben Affleck. I once interviewed for a job as a stockbroker when I was first starting out over 20 years ago, the senior broker was trying to be just like him. Although, being English, it didn’t work and just made him look like a wally. I walked out, not expecting a call back, and thankfully didn’t get one.

It’s got a similar feel to George Jay Huang’s Swimming With Sharks starring Kevin Spacey (I saw the play of Swimming With Sharks with Helen Bexendale and Christian Slater, which was excellent. I wish Spacey had done it at the Old Vic, but that doesn’t look like it’s going to happen now👀).

I’d always assumed that Boiler Room’s writer Ben Younger, had been a stock broker himself, but actually he just went for an interview and had the same experience as me.

It feels (now) as though it’s an original version of the Wolf of Wall Street. But a version where you only get a glimpse of the Jordan Belfort type brokerage boss, Michael Brantley, played by Tom Everett Scott. Even the firm’s name, JT Marlin, which was supposed to sound like JP Morgan, emulated Stratton Oakmont’s supposed legitimacy.

Wolf of Wall Street (2014)

The book is better than the film, and that says a lot because the excellent film directed by Martin Scorsese is a modern-day Goodfellas. Big budget, big scenes, big crimes and is amazingly based on the real life of Jordan Belfort.

Or to be more accurate, the life the Belfort wanted you to see. However, Scorsese does an excellent job of portraying the brokers as thieves rather than financial experts. Belfort claims in one of his many social media appearances that the only bit that was inaccurate was where he was violent towards his wife.

The scene where Matthew McConaughey takes a young Belfort out to lunch is hilarious, but I think many miss the point. You see young bucks chest thumping on social media talking about trading. But it’s actually a sad depiction of young innocents being corrupted by perceived wealth.

Case in point: I saw a contestant on The Apprentice yesterday about kids banking apps gleefully accepting praise that he was “looking a bit Wolf of Wall Street” today, when actually he was being told he looked like a criminal.

That scene though, is fairly typical of a broker lunch where you always have to listen to someone more senior than you drone on about absolute rubbish whilst they get drunk before noon on a Wednesday.

Margin Call (2012)

An excellent performance from Zachary Quinto (the serial killer from Heros), as the financial analyst that uncovered some overleveraged subprime mortgage debt trades during the 2008 financial crisis.

The complexity of the trades is slightly washed over, but it is quite realistic in that the entire financial stability of one of the largest institutions in the world can sometimes rest entirely on the shoulders of one trader.

But it’s a cold, dark, realistic movie, and despite everyone turning up to a board meeting in the middle of the night suited and booted, is a fairly good example of how banks don’t care what they trade or who they sell worthless investments too as long as they are off their risk book.

The Big Short (2015)

More of a finance film for Christian Bale, that American Physco where they didn’t really talk about investing, The Big Short is a quasi-documentary about a hedge fund that predicted the financial crash of 2008 as depicted in Margin Call, and placed a series of best on the housing market crashing.

It’s based on Michael Lewis’s book of the same name: The Big Short: Inside the Doomsday Machine. The sort of thing that you Gary Stevenson made all is money on and writes about in The Trading Game.

The film does a better job than most of explaining how the trades and markets work by having Margot Robbie explain it in the bath, but if you want the details read the book. It’s excellent, as are all Michael Lewis books about trading.

Wall Street – Money Never Sleeps (2010)

I was so happy to see Wall Street return, and I thought it was better than most critics did. But, almost sad to see how Gordon Gekko had become a relic and aptly too small time to be considered a major character as trading had moved on from making millions to billions.

To quote Gekko from the original, “At the time I thought that was all the money in the world. Now it’s a day’s pay”.

Shia LaBeouf does a good job as the new Charlie Sheen, whose cameo was cheekily true to life, plus it introduced the world to Tulipmania, which is more relevant than ever with meme stocks FOMO and cryptocurrency booms.

Dumb Money (2023)

Dumb Money is really just a pump and dump story of a guy on social media with a big following ramping a stock. I don’t see it as a David versus Goliath story at all. Yes, some small investors made a bit of money on the way up, but a huge amount also lost money as the GameStop share price fell after the hype.

I watched this on the plane home from Vegas once, which was apt because all people were doing was gambling on sentiment rather than fundamentals.

I’ve included it in this list because it’s too topical to ignore, and the GameStop saga is far from over…