It would be unfair to say that Wall Street: Money Never Sleeps "almost" works; for one thing, that's not actually true - it does work. It might not work the way audiences were expecting it to, but as impossible and presumptively unnecessary sequels go, the film is pretty close to successful. It shouldn't work, and there are a handful of tiny things that keep Money Never Sleeps from being a great movie, but Oliver Stone pulls off the impossible more or less by continuing the Gordon Gekko saga and bringing it into the stock market collapse of 2008.
Out of prison after serving 8 years for insider trading, Gordon Gekko (Michael Douglas) sets about rebuilding his life by writing and lecturing about the dangers of sub-prime loans and toxic assets, largely falling on deaf ears. What he really wants to do is reconnect with his estranged daughter Winnie (Carey Mulligan), a left-wing blogger engaged to Jake Moore (Shia LeBouf), an investment banker / day trader and Green energy enthusiast. When Bretton James (Josh Brolin) sets about the collapse of the firm Moore works at - and the subsequent suicide of its owner, Louis Zabel (Frank Langella) - Jake turns an encounter with Gekko into an opportunity to get even with James. Winnie's increasing discomfort with her father's presence puts a strain on her relationship with Jake, and it Gekko's intentions may not be so pure, either. Meanwhile, the housing bubble inches closer and closer to bursting, and the Federal government may have to bail everyone out...
Honestly, that shouldn't work. Most people heard that a sequel to 1987's Wall Street was in the makings and said "really?" The Cap'n was one of them, although I don't think I ever bothered writing about it here. Wall Street: Money Never Sleeps starts with Gekko's release in 2001 and then jumps forward to 2008, right before the collapse. It hits all of the major beats regarding the "why" of the market downfall: Jake's mother (Susan Sarandon) is a former nurse turned realtor that makes risky investments she can't pay off, Bretton causes the collapse of a major bank by leaking information about their toxic holdings, then makes money betting against its own interests. There are two board room scenes set in the Federal Reserve. This movie shouldn't work.
But it does, and that's kind of amazing. The key is that, although Wall Street was about the mentality that allows this film to happen, Money Never Sleeps is about the people. And the people carry the movie, even through a story we already know the ending to. Whether it was serendipity or not that a sequel to Wall Street began development right before the failure of major banks, Oliver Stone is merely using real life as a backdrop to logically extend the story of Gordon Gekko and the stock market mentality, and in that he succeeds.
The success of Money Never Sleeps, in large part, comes from an excellent ensemble cast, anchored by (and this surprises even me) Shia LeBouf. I haven't been too kind on the man in the past, but LeBouf's Jake Moore keeps the whole film running. Everything in the film is told from his perspective, and he stands toe to toe with some of the best in the game and holds his own. Despite appearances, Michael Douglas' Gordon Gekko isn't all over Money Never Sleeps; he's a major character, but Gekko is frequently relegated to the background. That being said, his character development doesn't get the short shrift; as (one of) the only returning cast members from Wall Street, Gekko has evolved since we last saw him, in expected and, frequently, surprising ways. When he takes over as Jake's mentor, there's a sense that more is going on than strictly manipulation, and Gordon genuinely regrets the rift with his daughter.
Speaking of which, Carey Mulligan takes what could be a thankless role and really brings humanity to Winnie Gekko. The part could easily be a cipher: daughter of the main "bad guy," liberal blogger who distrusts wealth and those who chase it, but Mulligan gives her an emotional core that keeps you invested in her relationship with Jake. Better still, there's a fantastic scene with Douglas and Mulligan outside a benefit that really sets up the stakes for how the rift happened, and how they see its outcome differently. Josh Brolin is also excellent as Bretton James, a wholly unscrupulous investment banker that takes an interest in Jake but who seems to lack any semblance of basic human interaction. It could be a one-note "villain" role, but like so many other actors in the film, Brolin takes one scene (a lake-side discussion with LeBouf) and elevates the character beyond stereotype.
While they aren't in the film as much, it is worth noting that Frank Langella, Eli Wallach, Jason Clarke, and Susan Sarandon are also fantastic, and each finds something to stand out with in a film swimming with roles. Austin Pendelton makes the most of a thankless role as the director of the Hydro Fusion project Jake is funding, and there's another cameo I'll get to below, which is interesting, although I'm not convinced it was necessary, and I'm not talking about Oliver Stone's small part as an art dealer.
The trailers are a little misleading, in that they set up a more sinister tone for Money Never Sleeps than the film actually delivers. Yes, there is a degree of cynicism and a hint of the cautionary tone of the first film, but Wall Street: Money Never Sleeps is an overwhelmingly optimistic film for an audience that isn't expecting that. Gekko is arguably the protagonist of the film, although his role is secondary to Jake's, and even though Gordon hasn't changed as much as he pretends, I still think you're going to be surprised at how Money Never Sleeps ends. It shouldn't be terribly surprising, considering that the mood of Stone's films have been more optimistic since World Trade Center, but I suspect many of the negative reactions have something to do with the fact that Money Never Sleeps is less of an indictment on Wall Street than, well, Wall Street was. Greed isn't good anymore, and while Gekko suggests it's "legal" at the outset, that's very much not the case by the end of Money Never Sleeps.
The reason that Money Never Sleeps only "almost" works is that there are small, but persistent, touches in the film that are a little too "on the nose." Stone has a fondness for visual metaphors, but he pushes it too far by including lingering shots on actual bubbles floating above the New York skyline more than once. If that weren't enough, a shot descending one of the skyscrapers is accompanied by the sound (and eventually a split-screen shot) of dominoes falling, tied to the stock market crash.
Stone is also quite attached to the soundtrack, which consists largely of songs from David Byrne and Brian Eno's Everything That Happens Will Happen Today, and has a bad habit of playing songs where the lyrics are perhaps too literal in describing character arcs and plot points. I understand why he chose the songs, and why Stone gravitated towards them, but they may be a little too perfect over the course of a two hour film. There's also a scene where Gekko bumps into Bud Fox (Charlie Sheen) at a benefit that doesn't really go anywhere. It's interesting, in that it provides a bridge from the Gordon Gekko in the first film to the Gordon Gekko in the sequel, but the presence of Fox is largely superfluous to the story, and considering that Gekko has plenty of other opportunities to establish growth, it's really more of an excuse to bring another character from Wall Street back.
Of course, not all of Stone's choices fall flat: there is a consistent intertextual connection to The Good, the Bad, and the Ugly (literally played out as Jake's ringtone, although it works more than it should) in Money Never Sleeps, although it remains up to the viewer to decide who's who (hint: Eli Wallach could still figure into it, if you so desire). Stone uses a myriad of split screens within split screens to mirror the dizzying pace of stock market jargon and floor-level dealing, as well as a clever misdirection involving an iris transition. Honestly, the things that keep the film from being great don't tend to dominate Money Never Sleeps; they simply appear in small doses throughout the film in such a way that you remember them while you're leaving.
The overall impression, however, is that Stone (and writers Allan Loeb and Stephen Schiff) crafted a film that defies nearly every negative possibility one could expect from a sequel to Wall Street. The film never feels superfluous or exploitative of the original and, more to the point, logically extends the themes of Wall Street into the twenty-first century. The acting is top notch across the board, and even if the positive tone is disarming at first, there is something to be said for Stone's lack of persistent cynicism in the face of financial crisis.
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