Beyond 'Wolf of Wall Street': The Top 9 Movies About Finance and Trading

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Initial reviews are in for Martin Scorsese’s Wolf of Wall Street starring his longtime collaborator Leonardo DiCaprio. (If you don’t want to know, look away now.)

With the depiction of anything-goes, dwarf-tossing debauchery due to hit theaters on Christmas Day, it seems an opportune time to revisit past Tinseltown tales of low morals in high finance.

In 2012, my colleague Vincent Trivett examined 9 Financial Documentaries That Will Change the Way You Think About Money and Investing. It’s a fine list of fact-based films, one that has subsequently swelled with this year’s Money For Nothing: Inside The Federal Reserve, a Liev Schreiber-narrated release which features an appearance by our own Todd Harrison.

But what of cinematic big-business offerings that are less concerned with education than entertainment, even at the expense of occasionally  playing fast and loose with the facts? Here, with apologies to Michael Moore, are nine movies of this ilk.

1. Wall Street

Our Hollywood endings start with the finance film by which all others are measured. Oliver Stone’s Wall Street (1987) arrived a mere eight weeks after the Dow’s (INDEXDJX:.DJI) worst ever day had ended the era of ’80s excess so indelibly brought to the big screen by Michael Douglas. His Oscar-winning performance as corporate raider Gordon Gekko, a pastiche of Michael Milken and Ivan Boesky, was intended as a reptilian caricature by son-of-a-stockbroker Stone. In the ultimate irony, however, as author Michael Lewis later remarked, “To the director’s dismay, thousands of financial hotshots dreamed of becoming” the man with the “greed is good” mantra. The movie, which had a budget of $15 million, grossed $43.8 million in North America alone. Its cultural impact was incalculable, from finance to fashion — witness the power-dressing clones with contrast collars, suspenders, and slicked back hair who would populate Wall Street for many years after Wall Street.

S&P 500 Index (INDEXSP:.INX) that year: up 5.25%. Rotten Tomatoes rating: 78%.

2. Working Girl

Working Girl (1988) told the rags-to-riches story of Staten Island secretary Tess McGill (Melanie Griffith), who toiled away in the M&A division of an investment bank before getting her big break when her boss broke a leg. This Mike Nichols-directed vehicle also starred Sigourney Weaver, Harrison Ford, Alec Baldwin, and Joan Cusack. It contained some memorable lines from the titular character (“I have a head for business and a bod for sin.”) and an earworm song (“Let the River Run”), which won Carly Simon an Academy Award. Very much a product of its time, the film featured unbelievably big hair atop shoulder-pad-sprouting yuppies. While no one would confuse Working Girl with Casablanca on artistic merit, the movie made a more than respectable $102.9 million worldwide and took home the 1989 Golden Globe Award for Best Motion Picture — Musical or Comedy.

S&P 500 Index that year: up 16.61%. Rotten Tomatoes rating: 84%.

3. The Bonfire of the Vanities

The Bonfire of the Vanities (1990) was based on Tom Wolfe’s book of the same name published in October 1987. (Yes, the very October 1987 in which Wall Street suffered the most cataclysmic one-day crash in its history. Popular culture is unerringly always one step behind the times.) That ode to Reagan-era extravagance unleashed unforgettable phrases like “master of the universe” and “social x-ray” upon the lexicon. Millionaire investor Sherman McCoy, so memorable on the printed page, shriveled in this box office bomb, however. It again starred Melanie Griffith, plus Tom Hanks (post-Big yet pre-big, before he went on to win two Oscars in quick succession), Bruce Willis, and an emerging Kim Cattrall. Novel adaptations of the moneyed set are notoriously tricky to pull off on the silver screen; see several not so Great Gatsby’s. Released in a recession, it gave off an instantly mildewed appearance, suffered from serious production problems, and endured a succession of A-listers passing on lead roles. Moreover, literary purists were severely critical of several liberties taken with the plot. Brian DePalma’s brainchild was never going to win Cannes’s coveted Palme d’Or, but perverse consolation arrived in the form of five Golden Raspberry nominations for the worst film of the year. A rainy day rental, at best.

S&P 500 Index that year: down 3.11%. Rotten Tomatoes rating: 16%.

4. Barbarians at the Gate 

Barbarians at the Gate (1993) was another flick that had its foundations in a book: the eponymous tale of the legendary leveraged buyout battle for RJR-Nabisco, published in 1989 and written by Bryan Burrough. (A fine year for finance literature; Michael Lewis’ Liar’s Poker was published almost simultaneously and is another prime candidate for the film treatment.) It featured James Garner as Nabisco’s CEO and Jonathan Pryce playing his billionaire nemesis Henry Kravis. Fred Thompson, later to run for president, made a cameo. This was strictly small-screen fare, appearing only on HBO, but it received the ultimate industry accolade of “Two Thumbs Up!” from Siskel and Ebert.

S&P 500 Index that year: up 10.08%. Rotten Tomatoes rating: 67%.

5. Rogue Trader

With rogue traders in the news anew, suddenly Rogue Trader (1999) feels freshly relevant. It starred Ewan McGregor (after Trainspotting, before Obi-Wan Kenobi) as Nick Leeson, a 27-year-old whose catastrophic $1.4 billion loss brought 233-year-old Barings, Britain’s oldest investment bank, to its knees overnight. The movie’s reviews were decidedly mediocre but Leeson’s life since being sentenced to six-plus years in a Singapore prison cell is surely sequel-worthy. His wife swiftly filed for divorce. Then came a diagnosis of colon cancer. And this year, after a spell as CEO of an Irish soccer team, a by now bald and bespectacled Leeson amusingly made partner in a financial advisory firm.

S&P 500 Index that year: up 21.04%. Rotten Tomatoes rating: 33%.

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