Top 5 Movie Guide: Leonardo DiCaprio

For this edition of the Top 5 Movie Guide, we take a look at some of our favorite films featuring Leonardo DiCaprio, star of this weekend's "The Great Gatsby". DiCaprio was born and raised in Los Angeles, son of a comic book artist (George DiCaprio). His parents signed him to a talent agency at a young age (at age 10 his agent suggested he change his name to a more "American friendly" Lenny Williams; thankfully for everyone, he chose not to), and he began work in commercials and television shows. After appearing in the final season of "Growing Pains", his career took a major upswing as he transitioned into film. Over the next few years, he'd go on to star in such films as "The Basketball Diaries" (1995), "Romeo + Juliet" (1996), and, the big one, "Titanic" (1997). (fun fact: the role of Dirk Diggler in "Boogie Nights" was offered to him at the same time as that of his role in "Titanic"; he had to choose between the two). As it was, James Cameron's epic made DiCaprio an instant A-list star, and one of the most notable teen heartthrobs of all time.

After "Titanic", DiCaprio became very selective with his roles. He's worked with a variety of great directors, including four times with his personal favorite, Martin Scorsese. One of the biggest efforts he makes when choosing his roles is not to fall into any typecast situations. He refuses to conform to any one type of character or genre, quietly becoming one of the most diverse actors working today.

There are few roles of note that DiCaprio has turned down over the years (aside from the aforementioned "Boogie Nights"), but a few of prominent ones are Neo in "The Matrix" (who in Hollywood didn't turn that role down?), Ed Norton's role in "Primal Fear", and River Phoenix/Christian Slater's role in "Interview with the Vampire". He's been nominated for three Oscars, but has some how managed to avoid a win to this point. He received nominations for his roles in "What's Eating Gilbert Grape" (1993), "The Aviator" (2004), and "Blood Diamond" (2006).

Hit the jump to see which of his films we selected as some of our favorites!

Alex Schopp -
Leo has been one of my favorite actors since he started taking on adult roles. Not that I disliked his earlier work, but it didn't generally stand out to me.

     1. The Departed (2006)

What's really interesting here is that I like Leo more than Mark Wahlberg, but "The Departed" was not at the top of his list. I think that's a combination of two things: 1) DiCaprio is easily my favorite role in this film. I'm so angry with Matt Damon at the end. 2) While Leo as a whole works better for me, there are a few select films of Wahlberg's I love more than any of Leo's.
     2. Catch Me If You Can (2002)
This is just an engaging character drama with lots of parts that fit together so well. Tom Hanks and DiCaprio have a really fascinating relationship in the film, and Steven Spielberg provides the story - based on true events, nonetheless - with his usual bit of charm. I love the time period, the soundtrack, and all of the supporting actors in the film.
     3. Inception (2010)
I need to give this movie more credit than I usually do. I always dock it major points for being more interested in its plot than most of its characters (I never feel connected to any of them), but at least they got part of it right. I analyzed this movie in my mind and discussed it with my friends more so than just about any other film I've seen in the last five years, so that has to be worth something, right? Plus, it's original sci-fi content, and I have to give that some love.
     4. Django Unchained (2012)
Depending on how this film works in subsequent re-watches over the next few years, I could see this climbing all the way to the top of this list. DiCaprio's role is smaller, which hinders it slightly on this list, but it's still one of the best in the entire film. This is the most unique role we've seen Leo in thus far, and it was a welcomed experience to see him exploring further challenges. I wonder if there's anything he can't do well?
     5. The Aviator (2004)
This film is so hard to judge. I think DiCaprio does a really good job in the film; his performance as Howard Hughes is quite intriguing. I enjoy the era that the film depicts, and it has a great supporting cast. But that being said, the film comes in just under three hours, which can be a bit daunting. Still, the craftsmanship all-around and the story it tells makes this one worth a watch.

Ben Foutch -

     1. The Departed (2006)

"Christ. I mean, a guy comes in here against every, every instinct of privacy and self-reliance he has and what do you do? What do you do, huh? You send him off on the street to score smack, is that what you do? You're fucking ridiculous!"
     2. Inception (2010)
"What is the most resilient parasite? Bacteria? A virus? An intestinal worm? An idea. Resilient... highly contagious. Once an idea has taken hold of the brain it's almost impossible to eradicate. An idea that is fully formed - fully understood - that sticks; right in there somewhere."
     3. What's Eating Gilbert Grape (1993)
"I'm having a birthday party, but you're not invited, but you can come if you want."
     4. The Quick and the Dead (1995)
" No no no no, you see it's a gun fight. We both have guns. We aim, we fire, you die."
     5. The Basketball Diaries (1995)
"First, it's a Saturday night thing when you feel cool like a gangster or a rockstar- just something to kill the boredom, you know? They call it a chippie, a small habit. It feels so good, you start doing it on Tuesdays... then Thursdays... then it's got you. Every wise ass punk on the block says it won't happen to them, but it does."

Derek Clem -
I'm putting performance on the back burner for this one. This list is based purely on Watchability. Had it been based on performance it would look 100% different.

     1. Titanic (1997)

The length probably makes its actual watchability pretty low, but my desire to always be watching this is high. It's just so hard to squeeze into a regular day. Plus I pop this in the player just to remind myself that Leo has the ability to smile.
     2. The Departed (2006)
I already liked this movie but I feel like it just continues to grow and grow on me. The tension and anxiety Leo brings to the role is coerced onto the viewer. Maybe this one would make my performance list after all?
     3. Catch Me If You Can (2002)
I think what the world needs is more Leo, Hanks, Spielberg collaborations. I don't know how we'd get there, but we need it. This movie is a lot of fun at every dynamic turn.
     4. Blood Diamond (2006)
Leo brings a great energy to the screen that we don't get to see too often anymore. Even though the movie is full of horrific scenes and scenarios, Leo's energy makes those scenes palatable for multiple viewings. Plus I dig his accent.
     5. The Aviator (2004)
I actually don't really care for Leo in this part. Physically, I don't buy him as Howard Hughes. But I do love putting this movie on to take a nice long nap. Those golden hues make for some cozy Z's.

Nathan Hinds -
For my money, Leonardo DiCaprio is the greatest actor of his generation. I don't really know who all fits in that generation, but it still feels right to say. I don't think there is a single role this guy couldn't play; there isn't a single weak spot in his game. Right now, I think I can say that DiCaprio is my favorite actor. You heard it here first folks! Can someone get this man an Oscar, please?

     1. Catch Me If You Can (2002)

I'm only one pick in and I feel like so many movies in DiCaprio's filmography could be deserving of the top spot. The reason this gets the top spot is 1) it's in my Top 10 Favorite Films, and 2) the film showcases the entire range of his acting abilities. We get to see everything from him in this movie - the serious side, the romantic side, the comedic side (a very underrated ability of his), and the emotional side. This role really allowed him to tap into his entire bag of tricks, and man is it a loaded bag.
     2. Titanic (1997)
This is one of the greatest films of all time, and one of the most notorious films that guys claim to hate, even though we all know they probably love it. It's the greatest disaster film ever, and features special effects that still look great today. It's a perfect example of how big of a spectacle a film can be. This was the first film I remember people talking about going to see multiple times in the theater. It was also one of my first instances where I perfected the art of having to cover my eyes, but slightly opening my fingers so I could still see, during a nudity scene. Take that, mom!
     3. What's Eating Gilbert Grape (1993)
This movie has the benefit of having another one of my favorite actors, Johnny Depp. If this had been the only film I'd ever seen Leonardo DiCaprio in, I would've fully believed he was just mentally disabled. Hell, I'm not convinced he isn't and has just been acting normal ever since; the role is that convincing! Anyway, this was the first example of a lasting trend that would see DiCaprio not earn an Oscar. This is the part where I deliberately break the rules and throw in a bunch of honorable mentions for some other films in which he should have won an Oscar: films like "Blood Diamond" (2006), "The Departed" (2006) (how did he make it through 2006 without an Oscar?), and "Shutter Island" (2010). In case you haven't figured it out, you should watch all of those films as well.
     4. Inception (2010)
2010 marks another year where DiCaprio had multiple films that could have garnered him an Oscar. "Inception" was one of the most ambitious and original films I've seen in years. Every time I watch it, my appreciation for it only grows. It has possibly the most epic soundtrack ever, and some of the most astounding visuals to ever be seen in a film. I'll also take this time to rip on the Academy some more for the fact that they have never given Christopher Nolan an Oscar for Best Director. Man those guys (and girls) suck. No offense Bigelow, but you were third in directing that year, and the gap between you, James Cameron and Christopher Nolan (who were #1 and #2 that year, respectively) wasn't even close.
     5. Django Unchained (2012)
This film broke a long streak of roles where DiCaprio only played serious characters. Like "Catch Me If You Can", it was another chance for DiCaprio to show his range as an actor, a range that I think many people had forgotten about. Even though you despise his character, he is fascinating. I love how he switches from joking around to being dead serious so smoothly (like when he wonders why slaves never killed their owners). It's such a hard thing to do, but he makes it look easy. Oh yeah, he should have won an Oscar for this as well. I love Christoph Waltz in this film, but he won for playing a character extremely similar in tone to the character he played in "Inglourious Basterds". For that reason, DiCaprio should have won.

Tracy Allison -

     1. The Departed (2006)

I've spoken about this movie several times before. It holds one of the esteemed spots on my favorite movies list (that exists only in my head, for now). It’s complicated and treacherous, and yet not too hard to keep up with. I love the casting -- of Matt Damon and Leo DiCaprio especially. It’s one of those perfect castings in that the actor matches the role so well, but since the ethics and character of these men are in major question and all twisted up the actors could almost switch roles and that would work too.
     2. Revolutionary Road (2008)
Before this movie came out, I was excited for another Winslet/DiCaprio team up, who wasn't And then, I heard Kate Winslet mention that they would only agree to do another movie together if their story was nothing like Titanic’s. It’s safe to say that was accomplished here. You know by now that I love movies set in previous decades and the set and costumes are great, they align perfectly with that stifling and yet sought after 1950’s suburban style. If you’re a fan of Mad Men, you might like this one. It’s along the same lines. After the war, people were ready to lead normal, boring, perfect lives. Sometimes the anxiety and stagnant feelings that this sort of life can create are enough to drive people to madness.
     3. Catch Me If You Can (2002)
There's a lot to love about this film. Firstly, a team up between Tom Hanks, Steven Spielberg, and Leonardo DiCaprio is sure to create some movie magic. Especially when the story of this mostly lighthearted cat-and-mouse fare is based in truth. What I love most about this movie is its ease of watchability, the great vintage inspired sets, DiCaprio’s effortless charm, and the relationship of the Tom Hanks and Leonardo DiCaprio characters. This lonely young conman has only the respect and friendship of the man trying to capture him. Compelling, indeed.
     4. Titanic (1997)
What can I say about Titanic that hasn't already been said? It affected everyone. I was in 4th grade when it came out and every single girl in my class started decorating her locker with pictures of Leo. I know that people take a lot of issue with the movie (the courtship lasted only three days, love doesn't work that way, etc.) but, I find myself drawn to this movie every time it’s on. It holds up well and it certainly thrust Leonardo DiCaprio into the world’s collective consciousness. It remains very important in that regard.
     5. Django Unchained (2012)
Leonardo DiCaprio is certainly a versatile actor, but have I ever seen him this evil before? It was enjoyable, in a sick Tarantino-esque manner. DiCaprio was sickly sweet and vicious with a calculating look and unpredictability that left you on the edge of your seat. There’s something truly phenomenal when you are watching a new movie intently thinking, “What the hell is this guy gonna do next?”.

There we have it, folks. Another week with plenty of variety for your viewing pleasures. Overall, 11 different titles were featured above, and seven in multiple variety. Still, no film appeared on all five lists, which is a bit surprising considering a few films in DiCaprio's filmography. The biggest winners were "The Departed" and "Catch Me If You Can", which each appeared on four lists. "The Departed" nabbed three first-place votes, while "Catch Me If You Can" grabbed one more. Both of these films double in high watchability as well as technical proficiency. If you're looking for an entertaining, well made film, you won't go wrong with either of these selections.

Three films hit on three different lists: "Titanic", "Inception", and "Django Unchained". That's an awesome trio of films that really does a great job showing some different genres DiCaprio can handle. "The Aviator" and "What's Eating Gilbert Grape?" were the only other films with multiple selections this week, each earning two picks apiece. Overall, just take a look at some of the directors in the two above paragraphs that DiCaprio has been able to work with over the years: Scorsese, Spielberg, Cameron, Nolan, Tarantino. That's quite the group. Obviously, when you're bringing directors of this caliber into the fold (and adding DiCaprio's acting talents, of course), you know you're going to get something pretty good.

As always, we hope that each of these selections helps you to expand your knowledge and appreciation of some of the best films that Leonardo DiCaprio has provided over the years, and guides you to better and more enjoyable all-around viewing experiences.

Happy watching!