5 Oscar-Worthy Leonardo DiCaprio Performances

django unchained_700x384Despite being one of Hollywood’s biggest stars for nearly two decades, there is one career milestone that continues to elude Leonardo DiCaprio: an Academy Award. First nominated as a teenager, DiCaprio has struck out all four times he’s been up for an Oscar, making him perhaps the most conspicuously snubbed actor of his generation. These five movies showcase just a few examples of his work that failed to bring home the gold—or, in many cases, even earn him an Oscar nomination.

1. Catch Me If You Can
Steven Spielberg’s warm-hearted caper required a star who could combine the effortless charm of a master scam artist with the bumbling innocence of an adolescent. DiCaprio pulled it off: As real-life con man Frank Abagnale, he made an incredible string of youthful frauds, forgeries and deceptions look plausible while portraying Frank as charismatic, sympathetic, sad and desperate all at once.

2. Django Unchained
Plantation owner Calvin Candie (DiCaprio) is a sadistic brat who forces his slaves into gladiatorial fights to the death. In this rare turn as an outright villain, DiCaprio plays Candie—one of the nastiest bad guys in Quentin Tarantino’s filmography—with mustache-twirling relish and rage. Although DiCaprio didn’t hold back, he also refrained from going too over-the-top.

3. Revolutionary Road
Although DiCaprio co-stars here with Kate Winslet, a glorified Titanic reunion this is not. Instead, the two play beautiful yet miserable suburbanites who fight with one another while fantasizing about breaking free from their mundane lives. DiCaprio is devastating as Frank Wheeler, a worker drone who longs to chuck it all.

4. The Departed
DiCaprio played it straight in this gangster masterpiece from Martin Scorsese, but the movie’s cat-and-mouse game between cops and criminals still gave him plenty of twists and turns to work with. As undercover cop Billy Costigan, and as with many of his performances, the chief pleasure comes from the strangely meta experience of watching DiCaprio embody a character who is himself a naturally talented and confident actor.

5. What’s Eating Gilbert Grape
The movie for which 19-year-old DiCaprio picked up that aforementioned first Oscar nom is a dark cult classic co-starring Johnny Depp. As Arnie Grape, DiCaprio serves as the brooding film’s heart and soul, playing the developmentally disabled little brother to Depp’s small-town grocery-store clerk. Though it underperformed at the box office, this is the performance that made audiences fall in love with DiCaprio.

You know who else has delivered scores of Oscar-worthy performances despite never actually winning an Oscar? John Cusack.