5 Reasons Leonardo DiCaprio Should Win Best Actor Oscar This Year (And 5 Reasons Why He Won't)

4. It Feels Like He Has Already Won (He Shouldn't)

What differentiates DiCaprio from other well-known actors who surprisingly haven't won before (including Gary Oldman, Johnny Depp, Brad Pitt, Ralph Fiennes, and Joaquin Phoenix) is his willingness to kowtow towards the Academy. Aside from maybe Inception and Shutter Island, DiCaprio's main mode of film he has appeared in for the past fifteen years is commonly referred to as "prestige pictures" (or derisively referred to as Oscar-bait). The aforementioned J. Edgar and Revolutionary Road along with The Aviator, Gangs of New York, and even Django Unchained all had Oscar-tailored performances by Leo. And the internet's obsession with DiCaprio's obsession of getting an Oscar only furthers the idea that he is an actor held in the same esteem as Oscar winners. Ironically, pointing out how strange it is that he hasn't won an Oscar has made it feel like he retroactively has. Sometimes repeated brushes with the Academy fosters repeated success (Meryl Streep, Daniel Day-Lewis), but DiCaprio could become more like the late Peter O'Toole who was nominated for Best Actor eight times but never actually received the award (although he did win an honorary Oscar). Furthermore, Scorsese himself didn't win an Oscar until 2006's The Departed despite multiple nominations. Leo doesn't even have the same cache as his immensely talented favorite director, so it could be a long time before he gets a win too.