Ever wonder who some of the best actors to never win an Oscar are? Sure, there is Brad Pitt (nominated for Benjamin Button and Moneyball), Johnny Depp (Pirates of the Caribbean, Sweeney Todd, and Finding Neverland), and Harrison Ford (Witness) among countless others. However, there’s that one name that always leaves me puzzled; Leonardo DiCaprio.
Leo got his first nomination at the ripe age of 19 playing Arnie Grape alongside Depp. Although he looked like he didn’t belong alongside Ralph Fiennes (Schindler’s List), John Malkovich (In the Line of Fire), and the eventual winner, Tommy Lee Jones (The Fugitive), he was praised by critics as a stand out playing a mentally handicapped adolescent. I don’t think he even knew what kind of career he’d be in for over the next 20 years.
His first big screen blockbuster was Titanic and it was one of the highest grossing films of all time. Although he received a nomination for a Golden Globe for his role as Jack Dawson, there was no such love from the Academy. Note about this movie: Rose totally lied when she told Leo she’d never let go. Probably why Leo has trust issues now. We’re here for you buddy.
With the new millennium came a turning point in Leo’s career. He was no longer taking any role he could get and was now able to be more selective with his movies. It started out with Catch Me If You Can. One of my all time favorite DiCaprio films, it surprises me that he didn’t get nominated for this film. Granted it would have been tough to beat out Daniel-Day Lewis in Gangs of New York.
Speaking of Gangs of New York, Leo also starred in that alongside Lewis. In it, he played Amsterdam Vallon, a young man that returns to the Five Points neighborhood in NYC during the 1860s to avenge his father’s death against “Bill the Butcher.” It received mixed reviews, some touting it as a magnificent portrayal of the a gang-lord in the 1800s, while others said that it strived to be great, but only came out as good. The most important part of this role for Leo seems to be the relationship he formed with director Martin Scorsese.
Scorsese and Leo joined back up two years later in The Aviator. If you need more proof of Leo’s devotion, he spent a year and a half in preparation for this role. It paid off for him as he earned his second Oscar nomination, this time for Best Actor. He lost out to Jamie Foxx, playing Ray in the self-titled movie about the music legend, but it wasn’t time for Leo to give up just yet.
Two years later the two met up again, this time in The Departed. This may be one of the best movies that I’ve ever seen. I won’t spoil the ending for you, although if you haven’t seen this I don’t want to talk to you, but it is one of the most mind blowing scenes in a movie to date. You have to catch it.
Anyways, he somehow didn’t even get nominated for an Oscar in this film. Yes, I know he was nominated for his role in Blood Diamond, but they really couldn’t have nominated him twice? I mean his roles in both films were way better than anyone else in the field. He went up against Ryan Gosling before he became Ryan Gosling. Will Smith in The Pursuit of Happyness was fine, but he wasn’t in the same league. Any movie that spells the words of their title wrong is automatically taken out in my book. Peter O’Toole is a phenomenal actor, and I’m sure Venus was great, but the movie isn’t even listed in his IMDB known for section. He couldn’t win the award. And then there was the actual winner, Forest Whitaker. Listen here Forest, I’m sure your movie was great and all, but could you please give Leo his deserving award. We’ll even let you choose which movie he wins it for, how does that sound? To this date, I don’t know how Leo got so screwed. Someone must have been jealous.
Taking a break from Scorsese in 2008 wasn’t the greatest life decision Leo ever made, but you can’t be good all the time. Body of Lies was decent, and Revolutionary Road was good, but they weren’t in the same league as his other films. He must have known what was coming up next because 2010 sure didn’t disappoint.
Shutter Island, another Scorsese collab, was fantastic, so I’ve been told. Looks great. Definitely need to see it. It just has to be two in the afternoon with all of the lights on and my door locked so no one can come in and out to surprise me. Enough about that though. Lets go into my favorite Leo movie and possibly just straight favorite movie of all time; Inception.
Four score and seven years ago, err I mean three, Adam was still in Iowa and he thought this was a movie we actually should pony up the arm and leg that the movie theaters charge at this point. It turned out to be a fantastic decision. Walking out of the theater, I was left with so many questions. Mainly, what the F just happened? How could someone come up with such a concept? A dream within a dream within a dream? I have a tough time remembering a dream, let alone many dreams. Limbo? Totums? If this wasn’t the best movie of the year I don’t know what was*. And Leo’s performance as a man just wanting to get home? He played it perfectly. Excuse me while I go watch this movie on repeat and still try to figure it all out.
J Edgar was over-hyped and could never live up to it’s potential so we’ll just brush past that one and move on the Django Unchained. Alright, confession time. This is awkward, but, uhh, I’ve never seen this before. Yeah, I know. What am I doing with my life? Leo as a plantation owner? Christoph Waltz? Jamie Foxx? I will watch this soon, I can promise you that. If only Netflix had it on their instant queue.
Next is Gatsby. Sorry, didn’t mean to sell him short. The Great Gatsby. We’ve all read the 1925 book by F Scott Fitzgerald, and maybe seen the Robert Redford 1970s version of this (it wasn’t that good), but this one lived up to the bill. The soundtrack. The vibe. The allure of the parties. It was just perfect. The 1920s never looked so good. The critics and fans weren’t as excited about it, maybe because it doesn’t have a Disney happily ever after ending, but Leo played Gatsby so well that I’d be shocked if he didn’t receive his 4th nomination for an Oscar. If you haven’t picked it up yet, I may be a little biased, but to each his own.
Finally we have his newest film, The Wolf of Wall Street, being released November 15th December 25th. Now this is a movie that will probably not win him any acclaim from the academy, but have you seen the trailers?! Hmm, Leo playing a wealthy man? Check. Crime? Check. Corruption? Check. How could you not love it? It’s basically a cross between Jay Gatsby and Frank Abagnale Jr. And if that is any indication of how great this movie will be, it is going to be a must see.
Leo DiCaprio will win an Oscar. One day. He’s been close. He will get closer. But I do believe that he will eventually win an award, hopefully before the Cubs do. And when he does, he will go down as one of the greatest actors of all-time.
*It was The King’s Speech. Damn you Colin Firth.
Editor’s Note: And this one.. is just because I found it. And what is happening here?