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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.

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.