Planswell’s top 15 best movies about money and business

Let’s talk movies and money. Particularly movies about money.

As someone who holds no shame in living the sweat-pant life while binging on movie popcorn on a Friday evening, there’s something overly satisfying about watching movies that involve money.. Lots of money.

Narrowing down a top list of 15 movies from several hundreds was no trivial task. From documentaries and mobster films to fantasy lifestyles and films about perseverance, these films were selected based on popularity, relatability and rating.

It’s time to grab your popcorn and pour your sodas because here’s our list of the top 15 best movies about money and business:

Highlighting the late-2000s financial crisis and recovery stimulus in his typical controversial fashion, Michael Moore plunges into exploring whether or not capitalism can be considered a sin and whether Jesus would be a capitalist. If you’re interested in uncovering the many sides of the financial crisis, this film is for you.

It wouldn’t be an accurate list without at least one mob inspired movie. Casino takes place in the early 1970s Las Vegas scene, where an up and coming mobster (featuring Robert De Niro) eventually heads the Tangiers Casino. At first, he’s a great success in the job, but over the years, problems with his loose-cannon enforcer Nicky Santoro (Joe Pesci), his ex-hustler wife Ginger (Sharon Stone), her con-artist ex Lester Diamond (James Woods) and a handful of corrupt politicians put Sam in ever-increasing danger.

Based on the true story of Frank Abagnale, Leo DiCaprio stars in this film as his character successfully cons his way to earning millions of dollars before the age of 19 by posing as a Pan American World Airways pilot, a Georgia doctor, and a Louisiana parish prosecutor. He became so experienced in cheque fraud that the FBI eventually turned to him for help in catching other cons. If you haven’t seen this film yet and if you’re wondering what life would like as a con, you’re in for a treat.

Things really start to heat up in this NYC real estate office when the entire sales team is given news that only the top two performers will keep their jobs by the end of the week and everyone else will be let go. Shelley Levene (Jack Lemmon) and Dave Moss (Ed Harris) come up with a plan to steal better leads from their superior, which ends up making things overly complicated for the two. If you’re in real estate, sales, or just love competition, you’ll want to give this film the time it deserves.

Matt Damon shows us a different side as he narrates this documentary showcasing explicit details of the 2008 global financial meltdown. This recession was the cause of millions of job and home losses that ultimately plunged North America into a deep economic recession. The documentary highlights a wide range of interviews and traces the story from the United States to China to Iceland to several other global financial hot spots.

“Show me the money!” This movie highlights the career of a slick sports agent, Jerry Maguire (Tom Cruise). Writing a heartfelt company-wide memo that gets him fired leads to crisis and chaos. Desperate to hang on to the athletes that he represents, Jerry starts his own management firm, with only single mother Dorothy Boyd (Renee Zellweger) joining him in his new venture. Banking on their sole client, football player Rod Tidwell (Cuba Gooding Jr.), Jerry and Dorothy begin to fall in love as they struggle to make their business work.

This film reveals the fascinating and true story of Molly Bloom, a young Olympic-class skier who notoriously hosted the world’s most exclusive high-stakes poker games for ten years before being arrested by more than a dozen FBI agents. Molly’s players included professional athletes, Hollywood royalty, business titans, and unbeknown to her, the Russian mob.

Bound by a tight budget, Oakland A’s manager Billy Beane, played by Brad Pitt, is faced with the challenge of reinventing his team by outsmarting the richer ball clubs. Joining forces with Ivy League graduate Peter Brand (Jonah Hill), Beane makes strides to challenge the old-school baseball traditions. How does he manage this? By recruiting bargain-bin players labelled as flawed by the scouts, but have game-winning potential. If you’re into movies about statistics, odds, and pushing the envelope, this film has your name on it.

A money movie classic and childhood favourite of many, it would be shocking if Richie Rich didn’t make the cut. Richie Rich, played by Macaulay Culkin, has exactly what any little boy could ever wish for: all the money, toys, and love by his parents that the world offers. What he doesn’t have are friends. After his parents suddenly go missing, he suspects an executive in the family company is responsible. Setting out to solve the mystery, Richie hooks up with a group of kids who prove they just might fill the void in his life, while helping him save his folks.

In this film, Wall Street guru Michael Burry (Christian Bale) comes to the realization that a number of subprime home loans are at risk of defaulting. Burry bets against the housing market by throwing more than $1 billion of his investors’ money into credit default swaps. His actions attract the attention of banker Jared Vennett (Ryan Gosling), hedge-fund specialist Mark Baum (Steve Carell) and other greedy opportunists. Together, they make fortunes by taking full advantage of the impending economic collapse.

Growing up in the mob, a young man works very hard to get noticed and advance himself through the ranks. While he enjoys the lifestyle of money and luxury, he is also extremely oblivious to the horror that he creates around him. A few mistakes ultimately unravel his climb to the top of the ladder and put an end to his greed.

A tear-jerking, emotional film that sheds light on the struggles of everyday life which includes financial and family stress. Evicted from their apartment, Chris Gardner (Will Smith) and his young son (Jaden Smith) find themselves stranded with no place to call home. The two of them ultimately live in shelters and endure many hardships, however Chris refuses to give in to the despair and continues to fight and create a better life for him and his son. To some degree we can all relate to this film in the sense we’re always striving to build a better life for ourselves, especially when it comes to our personal finances.

Jordan Belfort (Leonardo DiCaprio) takes an entry-level job in the late 1980’s at a Wall Street brokerage firm. By the early 1990s, while still in his 20s, Belfort starts his own firm, Stratton Oakmont. Together with his trusted lieutenant (played by Jonah Hill) and a band of brokers, Belfort makes a huge fortune by defrauding wealthy investors out of millions. However, their party doesn’t last long as the SEC and the FBI close in on his empire of excess.

An upper-class executive, Louis Winthorpe III (Dan Aykroyd), and homeless street hustler, Billy Ray Valentine (Eddie Murphy), cross paths when they unknowingly become the subjects of an elaborate bet by successful brokers and brothers, Mortimer and Randolph Duke. Winthorpe, who also happens to be an employee of the Dukes, is framed by the brothers for a crime he didn’t commit. Meanwhile, the Dukes bail Valentine out of jail, install him in Winthorpe’s former job, and grant him use of Winthorpe’s home. When Winthorpe and Valentine uncover the scheme, they set out to turn the tables on the Dukes.

Bud Fox (Charlie Sheen) is a 1980s Wall Street stockbroker full of ambition, doing whatever he can to climb his way to the top. While admiring the power of the unsparing corporate raider Gordon Gekko (Michael Douglas), Fox entices Gekko into mentoring him by providing insider trading. As Fox gets himself involved in greed and questionable schemes, his decisions eventually threaten the livelihood of his father (Martin Sheen).


P.S. if movies aren’t your thing and you’re more of the literature type then you’ll want to check out our list of the top financial planning books for Canadians.