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The Best Money Movies Ever?

I’ve been meaning to share this post for a while now.

Some of you will already know, I’m a huge film fan. There’s something deeply satisfying about watching a well-crafted film with a great story that draws you into a world created by someone’s imagination.

Or makes you laugh your arse off and forget all your troubles.

Well, whilst researching our last Excelerator, I discovered this absolute gem of an article by Andy Hart.

Andy runs a blog and podcast called Money Maven, which you can check out (along with the original article) here.

I couldn’t help emailing Andy to let him know I think he nailed…

…although I can’t believe he left out Trading Places & The Secret of My Success (Michael J Fox at the height of his powers!).

What do you think? Have we missed anything?


John Ndege made his third appearance on the Money Maven podcast, and in this episode, we discussed our favourite films, documentaries and TV series about money and business. It was a challenge for both of us, and as John said, films are designed to be entertaining, but rarely insightful or instructive, so picking a top five needed a bit of thought.

When I made my choices, I went off and Googled the shows, because while I have a memory of what happened in the film, it was interesting to read a plot description and refresh my memory.


We picked our top five each, which are listed below. We’d love to hear your thoughts, and if there’s anything you would add to the list, let us know. We’re always on the lookout for new things to watch. We didn’t tell each other what we’d chosen, which made the conversation a bit more interesting!


  • Only Fools and Horses – there weren’t a lot of entrepreneurial shows on British TV when I was younger, but this was one everyone watched. It teaches you the value of taking action.
  • Billions – the series about a federal prosecutor of financial crimes. It missed out on a place on the list in favour of more classic programmes.
  • Tony Robbins: I am Not Your Guru – the documentary of the motivational business mindset coach, a behind-the-scenes look at his annual five-day conference.
  • Casino – Martin Scorsese’s 1995 film based on the true story of running Mob casinos in the 70s and 80s.
  • Rogue Trader – Another true-story documentary, this time about Nick Leeson, who brought down Barings Bank through risky deals.
  • Betting on Zero – This is a new documentary, looking at Herbalife and the battle between two hedge fund managers.
  • Wall Street (and its sequel) –  the classic insider trading film from 1987.
  • Glengarry Glen Ross –  cult classic sales film.

While we picked five each, if I could include a sneaky sixth choice, it would be Glengarry Glen Ross, which is a cult film with a stellar cast – even the name sounds cool! It looks at a real estate firm trying to sell plots of land, with the staff hitting the phones and doing their utmost to make money.

It includes standout solo performances, with Alec Baldwin’s springing to mind immediately. Worth checking out if you haven’t seen it.


5. Office Space: Three company workers who work in an organisation with a terrible culture, famous for the so-called TPS Report. They decide to rebel against their boss to free themselves from a life of drudgery and wage slavery. The whole ethos of the film is that as an employee trying to make money, you should avoid a soul-destroying environment, those that are caricatures of the offices you see in Dilbert.

He thinks it’s instructive because it shows people that they have the power to take control of their life and not work somewhere like that. Since this film was made, companies have made an effort to at least pay lip service to the idea of having a good culture so that people aren’t completely demoralised by the challenges of working in a corporate environment – changing something stale into something vibrant.

It has been influential for knowledge workers, and it’s famous in tech circles, because it’s all about keeping your employees happy, and as businesses have moved towards being knowledge businesses, they realise that their most important asset is their people, and keeping them happy is essential to having a positive working environment.

Stu note: Absolute cult choice. Not sure it’s strictly a money film though?

4. Jerry Maguire: Tom Cruise plays the main part in another film about conviction. Jerry Maguire is a sports agent for a big firm, and he realises that the firm isn’t giving attention to the agents. He writes a memo which says: “this business would work better with fewer clients and less money”, which doesn’t go down well with the executives.

When he’s sacked, he challenges colleagues to come with him and form a company with fewer clients but better relationships – only one person joined him. The business struggled for a couple of years, but one client stuck with him and they formed a tight bond.

That client went on to become a star sportsman and many athletes wanted to join Maguire’s agency to have the same kind of relationship, which allowed him to be more selective about who he worked with.

It’s about conviction, and it was a moral issue because he believed that the business had been corrupted by money. What was needed to take care of agents wasn’t to have a large agency, but to work with fewer clients. Businesses can have a moral side to it.

Stu note: It may not be a popular idea, but Tom rarely makes a bad film and this was solid and strangely different from standard rom-com fare. The cut scenes of the Zig Ziglar character were great, with the final one telling how it is with balancing success in business with happiness in life.

3. Smartest Guys in the Room: The documentary about the collapse of Enron missed out on a place in my top five, but John included it. This was a great documentary because it exposed the fact that you can’t always trust so-called experts – Andersen’s accountancy firm continued to supply them with numbers even though they were incorrect.

The lesson here is to do your own research. When it comes to business, you can’t rely 100% on third parties; you have to educate yourself and find the facts out for yourself. There was a complete abuse of power by the employees and executives in the company, and it shows that money corrupts.

There were even blackouts in some of the places where they provided power, which was a deliberate ploy to then increase the prices of the energy services – Enron traded in utilities.

2. The Game: Michael Douglas plays the lead role of a reclusive, rich banker who lives alone in a mansion with his housekeeper. His brother disappears for years on end but turns up to give him a birthday gift – a roleplaying game. However, Douglas’ character thinks this is his real life – his business and life are threatened and he has to complete a series of challenges to try to get back to normal.

The moral of the story, of course, is that if you have the money you should use it for good and have some excitement, rather than being a recluse. It came out in 1997, and John would highly recommend it.

I’ve seen it, but I think I was too young because I didn’t understand or enjoy it much. It’s almost an elaborate prank played on his brother.

Stu note: One of those films that are oddly better when watched again?

1. For Love or Money: A bit of a strange one, but this is a personal choice because it impacted on John’s decision to pursue a career in entrepreneurship. Michael J Fox is a young man who works all day as a concierge at a luxurious hotel but has a dream of building his own hotel.

He doesn’t have the money to do this, but there’s a rich man in town who can finance his dream. Unfortunately, the woman he loves is dating this man, so he can’t ask for the money, because the woman matters more.

As you can imagine, in the end, he gets the girl and gets finance from another guest, and is able to build the hotel he wants. John’s lesson from this film is the importance of luck in money and business. The character persisted until he became lucky, and it really embodies the phrase: “The harder I work, the luckier I get”.


5. The Big Short: Based on the book of the same name by Michael Lewis, who’s written a number of books about finance and business. It focuses on the financial crisis of 2007, and Christian Bale plays the lead role of real-life hedge fund manager Michael Burry.

In the film, Bale’s character realises that house prices are overvalued and mortgage-backed securities are not what they appear under the bonnet, and he attempts to create a credit default swap market with some banks, believing that the market was going to go belly-up, essentially seeing a way to profit from this collapse.

He took big positions to short the market he’d created and used his hedge fund’s money to do so. His investors worried that this was a bad idea and urged him to pull out, putting pressure on him and obliging him to pay an insurance contribution to cover the shorting.

For years he held on, convinced that he was right, much to the disapproval of his clients. He froze withdrawals from the funds because he was sure he was right, and in the end, he made a profit $2.69bn (an increase of 489%), although he could have lost it all.

John felt that the lesson from the film is a conviction and the importance of holding onto that belief.

Stu note: Couldn’t agree more. Took what should have been a dry topic, and made it a character-driven masterpiece. Margot Robbie’s contribution was genius funny.

4. Brewster’s Millions: A bit of a curveball, but this film, from 1985, is one I’ve watched the most, and it’s got two great actors in it – Richard Pryor and John Candy. The loose premise of the film is that Brewster’s (Prior) long-lost uncle has died and left him some money.

Brewster is a broke baseball player in New York so the inheritance is welcome, but there’s a challenge: either take $1 million upfront or spend $30 million within 30 days to inherit $300 million. If he accepts the challenge he can’t tell anyone about it and he can’t own any assets, so no property or art, he can’t destroy valuable objects and he can only spend 5% on gambling or in donations.

I watched this as an eight-year-old and loved it. There are some great characters in it – shady lawyers, friends who are just hangers-on, and there are lots of subtle, deep and meaningful messages in it.

Stu note: Richard Pryor gave a free license to do Richard Pryor. It’s aged a little, but still awesome.

3. The Founder: This is a fairly recent film, where Michael Keaton plays the real-life, Ray Kroc, who worked for the oddball McDonald brothers, the founders of the fast-food chain of the same name.

Kroc had been a struggling milkshake salesman before he met the brothers when he was in his 40s, who placed an order for seven of his milkshake machines. He realised that McDonald’s were disrupting the entire process of selling food – they made preparation and service faster and more organised.

He wanted to get involved with the business and encouraged the brothers to expand and franchise, but the contract they signed wasn’t win-win for Kroc. A lawyer came up with a cunning plan to help him make more money – the money was in the properties, not the burgers.

Kroc then went all-in by setting up a property corporation and focusing on the franchise buildings. The corporation became so powerful it was then able to buy out the brothers. There’s a lot of controversy around the final deal, but the film shows that it’s hard to scale a business when you’re a perfectionist like McDonald’s. They weren’t open-minded enough to grow their restaurants.

Stu note: Michael Keaton on fire in a story that is frighteningly modern in moral.

2. Becoming Warren Buffett: A real-life documentary available on Netflix. It’s all about the mighty man and talks about where he’s come from, what he’s done and shares his typical day. He shares a lot of wisdom throughout the documentary.

I’ve watched a lot of documentaries about him and seen speeches he’s given, and this year’s Berkshire Hathaway annual meeting was turned into a podcast with about 10 episodes to listen to.

John said what stood out for him was the scene when he goes to the McDonalds Drive-Thru and has the exact change for his McMuffin. He has over $50m but counts his pennies to buy his food. He’d recommend people watch it, as it’s another example of conviction – so many people made him look stupid because of his idea of value investing until it finally paid off.

1. Boiler Room: It may be a cliché, and it’s very salesy and full of quotes and one-liners. It’s loosely based on the book “The Wolf of Wall Street” by Jordan Belfort, who is the poster boy for boiler room scams. In real life, he also has a great DVD series called Straight Line. Although he’s a bit of a rogue, he’s made a comeback and does a lot of public speaking and sales training.

The film focuses on a brokerage house J.T.Marlin, a company that sells stocks which may not actually exist, for inflated prices, essentially scamming people by focusing on their greed.

The term ‘boiler room’ originated when these companies sprung up and navigated between the rules and regulations of Wall Street. Unable to afford a Wall Street office, they had the cheapest office in the building – the boiler room.

The film follows the ups and downs of the company and the people who work there.

Giovanni Ribisi plays the main role, and Vin Diesel and Ben Affleck are also in it. It also has a great soundtrack!

The characters rip people off and sell them stocks and shares that don’t exist, which creates a whole culture around the boiler room and questions to ask. It’s a how-not-to-do, not a how-to! It focuses on people’s greed, and how easy it is to rip them off if you focus on that and manipulate human triggers.

John agreed that it’s a great film, and you learn a lot about sales and how to manipulate people into buying things by playing on their emotions and pressing buttons.

Manipulation sometimes gets a bad rap, because you’re not always doing it for yourself, and it’s hard to get people to things, whether they’re good or bad. It’s all about decisions and choices.

If you want to get in touch with John, you can visit his website or on Twitter @JohnNdege. Pocket Risk is a company that focuses on financial advisers and provides them with tools to improve the services with their end clients, and has customers all over the world.

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