The Top 10 Best Money Movies Ever Made

Long before I wrote a blog (and before we had two kids), I was an avid movie watcher — Maybe one movie a week.  These days, with a family, and a blog to babysit, my time is much more limited.  Now, I only watch a couple movies a month… so I tend to make absolutely certain they’re really good movies to watch before I invest my time watching one.

Usually I write about serious stuff here on this blog, and not a whole lot about the really fun stuff (like movies).  For today’s post, I’ve decided to relax that oh-so-serious format a little and write about a fun topic — The best money movies ever made!  Use it as a guide to find the really good money movies that are totally worth your time!

Let the movie list begin!

1. Brewster’s Millions (1985) – IMDB rating: 6.5

Brewster’s Millions is a classic 80’s comedy about a minor league baseball player (Brewster) who receives a $1 million dollar inheritance from a recently deceased great-uncle.  Most people would be thrilled to inherit money from a long-lost uncle, but there’s a big catch to this inheritance.

Brewster can take the $1 million dollars, or he can try to win the whole estate of $300 million by spending $30 million in 30 days. (That’s $70 million in 2019 dollars.)  While spending that much money might sound easy (just buy a bunch of houses, right?), he actually has to be flat broke at the end of those 30 days to win the $300 million.

That’s a lot harder than it sounds, and some of the ridiculous things Brewster spends money on get big laughs.  I think the hardest part of the spending challenge is that he can’t tell anyone.  All his friends and over-paid advisers just can’t understand why he keeps spending money so stupidly.  They try to give him good money advice, but they also enjoy his lavish lifestyle.  Does he win the $300 million in the end?  You’ll have to watch the movie to find out!

The most important lesson Brewster discovers in this epic journey, is that money can’t buy happiness.  After awhile, spending all the money ceases to be fun for Brewster.  In the end, he learns a powerful lesson about what’s really important in life.

The move is based on a 1903 novel by the same name, so if you enjoy reading more Project Gutenberg has the book for free.

2. MoneyBall (2011) – IMDB rating: 7.6

MoneyBall is a sports movie (based on a true story) about the general manager of the Oakland A’s baseball team, named Billy Bean (played by Brad Pitt).  As general manager, Bean needs to put together a competitive baseball team on a very limited budget.  By focusing his hiring process on hard statistics rather than scouting intuition, Bean finds overlooked players that have large perceived weaknesses.  Using traditional methods those players would never would have been hired.

At first, the strategy called sabermetrics appears to be a failure, but Bean convinces his boss to stay the course.  Eventually Bean’s team of misfits goes on to win a record breaking 20 games in a row.

On the surface the movie doesn’t appear to have much to do with money, but it absolutely does.  If you think of the team as Bean’s portfolio and the players as his individual assets, you realize the movie is very much about value investing and putting together a winning portfolio from undervalued assets.

The book on which the movie is based, is also excellent.

3.  The Money Pit (1986) – IMDB rating: 6.3

The Money Pit is a comedic tale of two first-time home buyers that stumble onto a large mansion for sale in out the countryside.  The home appears to be a very good bargain.  The house and grounds look extremely beautiful and the widow-owner appears to be a motivated seller.

The young couple gets easily sucked into buying the mansion.

After buying the house, they subsequently discover the home needs major renovations… just to be livable.

Arguments with contractors, a disastrous home renovation, and big cash flow problems lead to serious tensions in their relationship.  This is an absolute classic home buying/renovation comedy.  If you’ve ever owned a home before, this is a absolute must see movie that’ll make you laugh away the pains of home ownership.

Even if you don’t own a home, this hilarious movie will serve as a cautionary tale of buying too much home and getting in over your head.

4. In-Time (2011) – IMDB rating: 6.7

It’s been said many times — that time is money.  Quite literally when you think that most people have to trade their time for money.  In-Time takes this idea to its extreme — money literally is time.  Characters in this science-fiction film quite literally pay for things with time.  Each person in this world has a clock on their arm counting down, and when that clock reaches zero they die instantly.  By working, they can add time to the clock, but most people struggle to make ends meet.  Many have to ‘borrow time’ just to stay alive and pay rent.

The main character of the film, Will Salas (played by Justin Timberlake) lives that struggle daily, until one fateful evening when he saves a man with over 100 years on his ‘clock’, but is tired of living.  The man gives Will all his time, which allows Salas to travel to other Zones and see how the truly wealthy people in his society live.

The wealthy in this world are essentially immortal because they never run out of time.  They control all the businesses and inflation, making it nearly impossible for the little guy to get ahead, which makes Will Salas a very unusual person.  He sees the societal inequity for what it is, and decides to pull a “Robin Hood” move.  But the ‘time keepers’ are close behind, desperate to keep the time only in the hands of the rich.

In my opinion this is a great “money” movie that really deserves to be seen.  The struggle and difficulty with which people live in this society mirrors many of our real-world struggles today.  I guarantee if you watch this movie you won’t look at time the same way again!

5. The Big Short (2015) – IMDB Rating: 7.8

The Big Short is a movie that looks at the 2008 housing crisis through the eyes of three hedge funds that shorted the housing market when every big bank was calling it rock-solid and stable.  These hedge funds knew that when adjustable rate mortgages began to rise 2007 from the teaser rates initially offered, mortgage bonds would eventually collapse.  They saw the corruption, stupidity, and flaws in the mortgage market before anyone else did.  They shorted mortgage bonds and everyone thought they were crazy.  Along with it, they realized some of the big banks complacent in the fraudulent mortgage market would eventually fail.  They shorted those banks as well, and made huge sums of money doing it.

It’s worth saying that this is not a “feel good” kind of movie.  It ends on a depressing note (The Great recession), I but I feel this might just be the most important movie on this list.  Why? The movie goes to great pains to explain things like what a Mortgage Bond is, Credit Default Swaps, and CDO’s to the average viewer, and they do a good job of it.

If you ever wondered why the Great Recession happened, this movie does a great job of explaining why.

6. Wall Street (1987) IMDB Rating: 7.5

Wall Street is a place where dreams are made and lost.  I haven’t seen this movie in years, but it’s an absolute classic money-movie.  The movie tells the story of Bud Fox (played by Charlie Sheen), a stockbroker who wants to work for a ruthless corporate raider named Gordon Gekko.   Yes, this is the movie that spawned the phrase, “Greed is good!”.

Ultimately it’s greed that causes Gekko to hire Bud, because of insider information that Bud collects (which is of course illegal).  Bud and Gekko become weathy because of this illegal information, and the two ultimately hatch a plan to buy Bluestar Airlines.  Gekko plans to dissolve the company to profit from the pension fund, but Bud would rather save the company because his father works there.

Ultimately Bud hatches a plan to save Bluestar Airlines, but will he escape jail time?

I won’t spoil the rest of the plot, but this movie really shows off just how far a Wall Street raider-type will go just to make a buck — at the cost of decent people’s lives.  Ultimately the main character, Bud, learns the importance of living by the rules and the importance of running an honest business through hard work.  We also get to see the evil and uncaring attitude from which Wall Street operates to find short-term profits.

There’s also a sequel to this movie that wasn’t half bad either!

7.  Office Space (1999) IMDB rating: 7.8

OK, if you haven’t seen Office Space before, this is an absolute gem.  Go see it.  Right now!  This fantastic dark comedy satires the everyday work-life of a computer programmer named Peter Gibbons.  What makes the movie so fantastic is how realistic it is.  If you’ve ever worked an office job in front of a computer, you’ll be laughing your head-off at this movie.  From co-workers with a “case of the Mondays”, bad commute traffic, irritating bosses, downsizing “experts”, and smash worthy office printers — this movie pulls absolutely no punches when making fun of corporate office culture.

Peter (the main character) gets burned-out by his job, and seeks out a occupational hypno-therapist to help him with his lack of motivation and enthusiasm for his job.  The hypno-therapist puts Peter into a super-relaxed state without a care in the world, and then suddenly dies of a heart-attack while Peter is still hypnotized.  Hilarity ensues as Peter stops caring about work in his new “relaxed” mode.

Meanwhile the company is planning to lay-off Peter’s friends, which are some of the hardest workers at the company.  Together, the three hatch a hilarious plan take-back from an uncaring company, which almost does the main characters in because of a software bug.

Thankfully it all goes up in flames at the end, and the movie reminds us that life is too short to spend your entire life working at a job you hate.  It’s a great movie!  Check it out!

8. Trading Places (1983) – IMDB rating: 7.5

As the oldest film on this list, Trading Places might seem a little dated, and indeed it is.  The cars, computers, and telephones in this film are all good for a retro-laugh, but the core tenants of the movie still stand tall — What money does to a person is ultimately timeless.

Trading Places is the tale of poor man (Valentine played by Eddie Murphy) turned into a rich man, and a rich man (Winthorpe played by Dan Aykroyd) turned into a poor man — quite literally overnight.  The change is masterminded by the antagonists of the film, the brother-owners of Duke & Duke commodities brokerage firm.  They decide as an “experiment” to make a faithful hardworking employee into a poor man, and then take a homeless man off the street and turning him into a model employee at their firm.

Money quite literally shapes these two individuals and the actions they take throughout the film — ultimately cutting Winthorpe down a peg and lifting Valentine up a peg or two.  The two eventually catch onto this big scheme, and are understandably upset.  They also discover some illegal insider trading by the Duke brothers, and decided to get revenge by destroying them (and make themselves a bundle of money in the process).

9. Fight Club (1999) – IMDB rating: 8.8

At first glance, Fight Club doesn’t seem like a movie about money.  It’s a movie about anti-consumerism, loneliness, and insanity.

The unnamed-narrator of the film originally starts his life seeking out consumerist perfection, as directed by his parents.  Only to find this consumer life made him completely unhappy and unsatisfied.  Returning home from a business trip one day, he meets a “soap salesman” named Tyler Durden that changes his life.  With Tyler, the narrator starts a “fight club”, and quits his job.  Together, the two introduce the new fight club members to their anti-materialist, anti-consumerist ethos.

This “club” eventually becomes an anti-consumerist terrorist group, but the important part of the film is really the narrator’s journey as he escapes a world of mindless consumerism for… something else.  A different kind of life.

If you ever get tired of collecting “nice things” and wonder what life should be all about — this movie is definitely a great movie to watch!

10. The Wolf of Wall Street (2013) – IMDB rating: 8.2

Rolling in at number 10 is The Wolf of Wall Street.  The movie is a true story, based on the life of Jordan Belafort when he was a stock broker back in the 80’s and 90’s.  If there’s one single movie that showcases the excessive and disgusting behavior of Wall Street during that time, this is it.

The main character, Jordan Belafort, starts a boiler room securities firm called Stratton Oakmont.  It was a basically a pump and dump shop (yes, it really existed), that profited by selling penny stocks the firm owned to mom ‘n’ pop retail investors through hard sell techniques.  This was securities fraud, and clearly illegal, but Jordan Belafort became immensely wealthy… for a time.

Of course you don’t get that wealthy doing illegal stuff without spending some of it — so the excess to which he took to spending his wealth is undeniably entertaining.

This one is definitely NOT a movie for the kids.  Definitely watch it after they’ve gone to bed.

I don’t know how true all of it is, but the excesses to which Stratton Oakmont and Jordan Belafort went were legendary enough to inspire a second money movie called Boiler Room.  That’s also a good movie, but the Wolf of Wall Street is probably the more factual of the two.

The movie serves as a very strong warning to anyone who hands their money over to Wall Street.  Be very careful you aren’t handing your money to charlatans like Jordan Balafort… and never trust a salesman when buying an investment.  Do your own research first.

If ever there was a showpiece for why individual investors should stick to index funds and avoid stock brokers — this is it!

Bonus Round!

Well, these are just my favorite picks for the all-time best money movies ever made.  Opinions on movies always vary, so I’d like to ask your thoughts on the subject matter.  Have you seen all these movies?  Am I wrong?  Is there a better money movie I’m missing?  What are your favorite money movies?

For bonus points, try to answer the following questions in the comments below:

• Which actor plays in a total of three of these top 10 films?
• Which movie had the largest (inflation adjusted) budget?
• Which movie was the most financially successful (also adjusted for inflation)?
• How many of these films are based on books?

[Image Credit: Flickr]