Believe it or not: Leonardo DiCaprio has never won an Academy Award, despite incredible performances in What's Eating Gilbert Grape (1993), Titanic (1997), The Aviator (2004), The Departed (2006), and Django Unchained (2012). In 2013, the 39-year-old actor stars in two films—both of which have received Oscar buzz and see him playing a thirtysomething, money-making, super-tailored, party-throwing guy. With July marking the halfway point to the red carpet, it's the perfect time to ask: Which grand New Yorker do you think will play to the Academy—Jay Gatsby in The Great Gatsby or Jordan Belfort in The Wolf of Wall Street? See our handy comparative chart, below.
New York locale: West Egg, Long Island (Great Neck)
Era: The Roaring Twenties—right before the market crashed.
Book adaptation: The Great Gatsby by F. Scott Fitzgerald
Sidekick: Nick Carraway (Toby Maguire)
Net worth: $1 billion, according to Forbes, not including all the illegal champagne on the premises.
Wardrobe: Boating blazers and unnecessary canes.
Non-period music: Mash-ups of Jay-Z, Lana del Rey, and will.i.am.
Big-shot director: Baz Luhrmann
Academy appeal: Insider gossip suggests the nomination could go to Best Visual Effects, Best Cinematography, and Best Costume Design—not best actor.
Occupation: Entrepreneur/broker/con man
New York locale: Financial district
Era: The go-go nineties—right before the market crashed.
Book Adaptation: The Wolf of Wall Street by Jordan Belfort
Sidekick: Donnie Azoff (Jonah Hill)
Net worth: Possibly $100 million, according to the New York Times, not including all the cocaine that goes up his nose.
Wardrobe: Khaki pants, a gold watch, and unnecessary boat shoes.
Non-period music: "Black Skinhead" by Kanye West
Big-shot director: Martin Scorsese
Academy appeal: The Academy may punish Leo's antihero for not being an activiste like recent winners past (Lincoln, The Artist, The King's Speech, Milk), but if he's going to get a nomination, it will be for this film.
—Laura Delarato. Follow her at @lauradelarato.