How to Make a Good 'Great Gatsby' Movie: A Guide for Baz Luhrmann
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Deadline magazine started a new round of Hollywood gossip last week with the news that acclaimed director Baz Luhrmann—the auteur of Romeo + Juliet and Moulin Rouge!—was casting for an adaptation of F. Scott Fitzgerald's classic The Great Gatsby. Luhrmann has reportedly already chosen his two male leads, with Leonardo DiCaprio playing Jay Gatsby, and Tobey Maguire as narrator Nick Carraway. The role of Daisy—Gatsby's beautiful, spoiled love interest—however, is still up for grabs.
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According to Deadline's sources, the poised English beauty Rebecca Hall workshopped the part with DiCaprio and Maguire, and though she remains in the running, Luhrmann is "casting a wider net." Deadline provided a list of actresses under consideration by Luhrmann, and it's a who's-who of young female stars: Keira Knightley, Amanda Seyfried, Blake Lively, Abbie Cornish, Michelle Williams, Scarlett Johansson, and Natalie Portman.
Though Luhramnn's take on the classic is promising, let's be honest—other directors haven't fared so well as they've tried to re-imagine Gatsby for the screen. The book is forever a target for adaptations. It's one of those all-too-rare American classics; a staple of high school and college lit courses, but also a perennial favorite among American readers—intellectually complex, magnificently styled, and terrifically readable. As Time put it in their Best Novels Since 1923 list: "It's not only a page-turner and a heartbreaker, it's one of the most quintessentially American novels ever written."
But as beloved as the book is, the films have been mostly panned. Past adaptations watered down Fitzgerald's narrative. They missed the book's themes. Or they simply got basic details wrong: As I tried to imagine a blonde Rebecca Hall, for instance, I suddenly remembered that Daisy was dark-haired ("hair lay like a dash of blue paint across her cheek" and "he kissed her dark shining hair"), despite Mia Farrow's very blonde portrayal in Francis Ford Coppola's 1974 version. This adaptation, which also starred Robert Redford, is the most memorable of the Gatsby movies, but it's considered by many critics to be melodramatic and hollow, not to mention too liberal with the soft filter. (Having re-watched the movie this week, I'd agree.)
So where did other directors go wrong? And who didn't play a great Daisy? To help us answer these Gatsby questions, we're revisiting the four main movie adaptations, from the silent film era all the way to (believe it or not) Mira Sorvino and Paul Rudd.

Scribner
1926: The lost (silent) film
Only a year after the book's release, Fitzgerald sold the rights for the very first version of the film for $45,000. It was a silent film, based on a popular stage adaptation of the book that had opened on Broadway earlier that year. In this first iteration, Jay, Daisy, and Nick were played by rising stars of the silent era: Warner Baxter, Lois Wilson, and Neil Hamilton.
Film scholar Wheeler Winston Dixon has said that this may have been the most "authentic" adaptation, but alas, modern day viewers will never know: all known copies have been destroyed. Although a rare hardcopy of the movie trailer exists, even that is hard to come by. Nevertheless, critics in 1926 gave it mixed reviews, noting that the movie was more popular entertainment than thoughtful art.

Paramount
1949: Gatsby with sound
In 1949, the first Gatsby adaption with sound was released by Paramount, with Betty Field as Daisy and Alan Ladd as Gatsby. But that movie hardly resembled the novel. Here, as in later versions, Fitzgerald's thematically-complex narrative was reduced to a Romeo and Juliet love affair. As the New York Times wrote when the film came out, "[W]ith particular emphasis upon the aspects of the sentimental romance... most of the tragic implications and bitter ironies of Mr. Fitzgerald's work have gone by the board in allowing for the generous exhibition of Mr. Ladd.". Critics noted that Field was miscast—too self-assured and strong for Daisy—and that the ironically upbeat '20s vibe of the book had been replaced with an oddly dark, noir-like mood. Gatsby's bootlegging, much as it would be in the later two films, was also exaggerated for dramatic effect, so that he looks more like a gangster than the nonviolent character of the book. In short, Fitzgerald's work was remolded to fit what was popular at the time.

Paramount
1974: Coppola, Redford, and Farrow
With Francis Ford Coppola on the script, and Robert Redford and Mia Farrow—six years after her critically acclaimed turn in Rosemary's Baby—set to star, the 1974 version had all the makings of success. And, with multiple Oscar and Golden Globe wins, love it or hate it, the 1974 picture stands as the most memorable adaptation.
But many would agree with Vincent Canby's critical Times review of the film, in which he wrote that the film was "as lifeless as a body that's been too long at the bottom of a swimming pool."
While Gatsby is a fast-paced read, the movie drags; there are too many glamour-shot close-ups of flowers and champagne bottles and pretty, crying faces. ("It's frivolous without being much fun," Canby wrote.) Even more than its predecessor, the movie focuses on—and sentimentalizes—the relationship between Gatsby and Daisy, and yet, their connection feels more contrived than ever. Roger Ebert, as always, put it best:
Nor, to be honest, can we quite understand what's so special about Daisy Buchanan. Not as she's played by Mia Farrow, all squeaks and narcissism and empty sophistication. In the novel, Gatsby never understands that he is too good for Daisy. In the movie, we never understand why he thought she was good enough for him. And that's what's missing.
Perhaps Canby hit it on the head when he wrote, "Mia Farrow is lovely, eccentric and unfathomable as Daisy, which may be an impossible role, one that is much more easily accepted on the page than on screen." That's exactly what makes Daisy so hard to cast now—and why it's fun to discuss the possibilities, as Jezebel and others have. Daisy is a bundle of contradictions—charming; naïve; self-serving; confused; shallow; beautiful; childish—she exudes class, but she has a vulgar side (Fitzgerald famously wrote that "her voice was full of money"). It's a much more difficult, and thankless, role than Nick—played excellently here by Sam Waterston—and even Gatsby.

A&E
2000: Straight-to-TV
Produced by A&E to air on the network, the most recent film-length adaptation has the least production value of the four but still boasts a cast with a fair amount of name recognition. Yet despite its competent production and talented cast, the casting choices all seem off, and the performances are wooden or mannered. Though an odd choice for Nick, Paul Rudd is perhaps the most likeable. Toby Stephens, on the other hand, looks uncomfortable playing Gatsby—all toothy-grin and no depth—despite his success in other literary adaptations. And Mira Sorvino, so good in Mighty Aphrodite, is perhaps the most miscast of all. Her Daisy doesn't seem like Fitzgerald's Daisy at all—charming, yes, but too assured and one-dimensional; Sorvino plays her as if she's the heroine of the film, which she was never intended to be.

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201?: Leonardo DiCaprio, Tobey Maguire, and ...
So, what does this tell us when discussing who should play the next Daisy? He needs an actress who can charm—at least in the beginning—Gatsby and the audience more than Farrow's Daisy did; someone who's capable of displaying more vulnerability than Field did in her version; and an actress who naturally exudes class but is also willing to show Daisy's darker, manipulative side. And the director of Romeo + Juliet hopefully won't resort to the Hollywood fallback of reducing Fitzgerald's novel about class and the American dream into nothing more than a tragic love story.