For Hemingway's first wife, Hadley Hemingway, we can think no one could better counterpart for Gyllenhaal than Natalie Portman (Gyllenhaal actually interviewed her in our August 2009 issue). Portman has played her fair share of empowered women (Closer, V for Vendetta), but we know she is capable of absolutely anything, so it would be interesting to see her play a more understated character. Though Hadley and Hemingway divorced in 1927, we'd like to watch Portman and Gyllenhaal portray the couple in their glory days.
Arguably one of the most incoherent yet brilliant writers of the 20th century (see the end of Finnegans Wake if you want proof), Irish novelist James Joyce was an influential figure in the 1920s Parisian literary scene. We like seeing Scottish actor James McAvoy in daredevil mode as much as the next person, but it's time for him to take a break from his X-Men superhero pursuits. He could even just do an Irish version of Robbie from Atonement and that would more than pacify us. McAvoy is busy filming a film adaptation of Frankenstein, but we humbly suggest he continue on the novel-to-film adaptation spree and follow that up with A Moveable Feast.
Nobel Prize-winning author Ernest Hemingway produced some of the most renowned novels of the 20th century, and his years as a young writer in Paris provided a crucial foundation for his literary career. A larger-than-life personality, Hemingway was a war hero and gun-slinging womanizer with an enthusiasm for hard drinking and a talent for modernist prose. Jake Gyllenhaal has the dramatic gusto and range of experience to portray Hemingway as a newlywed, recent expatriate and budding writer. Gyllenhaal has done his fair share of blockbusters, but his performance in 2005's Brokeback Mountain proved he is capable of portraying a tormented and impressionable character.
Catherine Keener is no stranger to embodying literary legends, having been nominated for an Academy Award for her portrayal of Harper Lee in Capote (2005). Though Keener is well versed in playing slightly oddball and humorous characters, she has the versatility to tackle the role of beyond experimental writer Gertrude Stein. Kathy Bates did a great job as Stein in Midnight in Paris, and it would be interesting to see another talented actress's interpretation of the character. We could see Keener's take being less perennially cheerful and more focused on the mentor aspect of Stein's role in the Paris literary scene.
We can't help but let our perception of Zelda Fitzgerald be influenced by Alison Pill's enthusiastically unstable portrayal in Midnight in Paris, but—fictional representations aside—F. Scott's wife was, by all accounts, quite a handful. Dubbed by her husband to be "the first American flapper," she and F. Scott were celebrities on both sides of the pond. Anna Kendrick is more than capable of Zelda's bubbly, Southern belle personality, and her darker, schizophrenic elements would be just the right kind of challenge for Kendrick. Plus, it's time she leaves all things Twilight and Pitch Perfect behind her and tackles a period role.
With that impish smirk and penchant for innocently delivered wisecracks, we'd like to suggest Joseph Gordon-Levitt for the role of The Great Gatsby author F. Scott Fitzgerald. We know he's more than capable of playing the lovesick puppy (as evidenced throughout the entirety of 500 Days of Summer) but we're interested to see what he can bring to the table in the passionate but volatile relationship that he reportedly had with his wife, Zelda. Plus, he would look unbearably cute with Anna Kendrick... how has no one thought of this before?!