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

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In its depictions of the Street, Hollywood has given us a few hits and many misses. Here are some of the former.

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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.


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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 (afterTrainspotting, 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%.
6. Boiler Room
Boiler Room (2000), with its seriously shady college dropouts selling schlock to unsuspecting investors in illegal pump-and-dump schemes, may be the closest kin to penny-stock-pushing Jordan Belfort of Wolf of Wall Street infamy. The film, starring Giovanni Ribisi, Vin Diesel, and Ben Affleck, paid homage to pre-tech wreck day traders at the end of the millennium. (The movie opened on February 18, 2000. Right on cue, Nasdaq topped out on March 10.) In a hall of mirrors scene, these latter-day GlengarryGlen Ross Gordon Gekkos actually watch Wall Street while reciting its best bon mots. This compelling tale of cold-calling criminals peddling shell companies clocks in at an even two hours and earned $16,970,581 domestically. The Wall Street Journal movie critic Joe Morgenstern was won over, declaring, "Ben Younger's debut feature has dramatic energy -- and money hunger -- to match the giddy heights of the Dow at the time it was made."

S&P 500 Index that year: down 9.11%. Rotten Tomatoes rating: 67%.
7. Capitalism: A Love Story
Including Capitalism: A Love Story (2009) on this list is admittedly a little like waving a red flag in a bull market but, hey, I wasn't about to inflict this year's unwatchable Assault On Wall Street upon you. Michael Moore's movie, a Weinstein Studio offering, is indeed nominally a documentary. Yet, as ever with the Michigan auteur, some of the material isn't exactly of the unimpeachable just-the-facts variety. Variety did, however, call it "One of his best films to date" and the reviews were mostly favorable, even if it couldn't quite recoup a $20 million budget. Moore's ambush tactics aren't for everyone, but Elizabeth Warren, in particular, makes for gripping viewing in this depiction of the post-Lehman landscape. The title is, suffice it to say, intended as ironic. Although with Wal-Mart (NYSE:WMT) - an especially acute object of Moore's ire - now selling Occupy Wall Street posters, satire is itself surely beyond parody.

S&P 500 Index that year: up 26.46%. Rotten Tomatoes rating: 75%.
8. Money Never Sleeps
Wall Street, arousing from a 23-year slumber, suddenly stirred with its sequel Money Never Sleeps (2010). By this time, a considerably grayer Gordon Gekko, sprung from his cell at Sing Sing, had long since swapped limos for subways. It's a rare follow-up that does justice to the original, and Oliver Stone was unable to catch lightening in a Cristal bottle twice. Lingering nostalgia for the first film saw this one do decent, but not boffo box office business. A brick-sized 1987-era mobile phone made a funny early appearance, and David Byrne again supplied much of the mood music. Yet this version, which briefly reunited Michael Douglas with Charlie Sheen in an ensemble cast that also included Shia LaBeouf, Josh Brolin, Carey Mulligan, and Frank Langella, was oddly unfocused. A detour to London (demonstrating how genuinely global the financial world had become in the interim) competed for air time with a convoluted estranged-daughter narrative.

If nothing else, the movie was a paean to product placement. Carey Mulligan's character ran her news website on a ubiquitous Apple (NASDAQ:AAPL) laptop - all the while railing against unfettered capitalism to her prop trader boyfriend. And Gordon Gekko had a fake Twitter (NYSE:TWTR) feed. (Like many Twitter accounts, it has remained untouched for over three years. No wonder such user disengagement was a key reason behind this week's rash of rating reductions.) Alas, even Gekko's on-screen appearance at Borders to promote Is Greed Good? in 2010 failed to prevent the bookseller from going belly-up in 2011.

S&P 500 Index that year: up 15.06%. Rotten Tomatoes rating: 55%.
9. Margin Call
Margin Call (2011), an indie production featuring MIT PhD graduates in the mortgage backed securities milieu, was never going to be a bona fide blockbuster. Yet this portrayal of multi-billion dollar bets gone badly wrong in the era of the Great Recession, made on a shoestring $3.5 million budget, debuted to high praise at Sundance. Its stellar cast included Kevin Spacey, Jeremy Irons, Stanley Tucci, and a rail-thin Demi Moore. Screenwriter and director J. C. Chandor recently told the New York Times magazine, "Always remember that the person (character) probably doesn't think that they are evil in any way," a propos of Margin Call. Such an honest approach was a hit with audiences. Indeed this critically acclaimed darling was hailed by The New Yorker's David Denby as "…one of the strongest American films of the year and easily the best Wall Street movie ever made."

S&P 500 Index that year: up 2.11%. Rotten Tomatoes rating: 88%.

No positions in stocks mentioned.
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