Leonardo DiCaprio has long been considered one of the true greats in the film industry. In the past few years, there has unfortunately been too much attention put into his lack of Academy Award success rather than his lifetime of amazing accomplishments. DiCaprio, I believe, puts himself into the life of a film so conclusively that the role can be easily overlooked, as has happened a few times in the past. The true measure of the acting legend is in the success of his films. Leo has proven to be a lottery for filmmakers, producing amazing and marketable performance after amazing and marketable performance. His roles, and often by consequence his films, are more often than not, great.
So where does Leo measure up? Well, it’s difficult to say. He has shown to be one of the more versatile actors in the world, his career has been prolific—lasting now over 23 years—and he’s been a household name for nearly as long. One of the most talented actors in the game today, Leo is also one of the most beloved, both by film fans and his peers. But with such a monumental portfolio, how can we narrow down his best moments? Well, we’re going to at least try. Here are the best of Leo’s scenes over his glorious career.
14. Last Call – Blood Diamond
When Leo calls Jennifer Connelly’s character at the end of Blood Diamond, the scene seems to capture the quality of Leo’s entire performance—his character’s convictions, his acquired South African accent and his physical transformation are all put on display. One of the more emotional moments of the film, Leo showcases the little nuances in his character to perfection. While the film itself may not be as beloved as many others on this list, the role Leo plays was once, and still should be, considered one of his best.
13. Chiseler – Gangs of New York
The bar fight that Leo gets into with McGloin after he’s called a “chiseler,” well not actually, but after a back and forth it’s agreed upon that a “chiseler” is a good comparison for what he is actually called. The entire exchange gets to show Leo under the watchful eye of Bill the Butcher (Daniel Day Lewis), and when those two get to share the same screen, it’s going to be a good time. While Day Lewis may outshine DiCaprio a bit with a much more dynamic character, they both prove to be head and shoulders above the vast majority of their peers.
12. Jack’s Death – Titanic
Even though the scene has been satirized to death and mocked for the selfishness of Rose (Kate Winslet), even by Winslet herself, this scene is still one of the more recognizable and powerful scenes in Leo’s collection. As he freezes in the icy water, Jack Dawson (DiCaprio) speaks to Rose of her growing old and dying in her own bed. The role catapulted Leo into A-List stardom and he never looked back, literally; it’s now said that Leo is embarrassed of the performance.
11. Bar Scene – The Departed
The Martin Scorcese crime drama, The Departed, gave us a different side to Leo, a darker, grittier version that we had only seen glimpses of. There are really two bar scenes that show this side best. The first has Leo order a cranberry juice then smash a glass over his mocker’s head for his comments about it. The other has his cast ripped off and Jack Nicholson smashing his broken hand with a boot asking if he’s still a cop. The fresh-faced Leo is able to look tough and little crazy in this role, showing that he’s much more than just a pretty face.
10. Finally Caught – Catch Me if You Can
Spoiler Alert: When Tom Hanks finally catches Leo at the end of Catch Me if You Can, the discussion between the two legends is a display of masterclass acting. Both giants work off each other brilliantly, and it’s a nice conclusion for the incredibly dynamic character of Frank Abagnale (DiCaprio). With Frank, Leo really gets to showcase his acting chops. An actor playing the part of a young con man makes for an interesting performance, and one that deserves the recognition it got.
9. The Pep Talk – The Wolf of Wall Street
Another beloved DiCaprio role, Jordan Belfry is a character that works with Leo’s status; it almost feels like Belfry could be similar to DiCaprio in real life, if we didn’t know better (of course). “The Pep Talk” is the scene that most people talk about when they think about Leo’s role in The Wolf of Wall Street. His arrogance and insanity really powers through in his speech as he pumps up his team.
8. Mal’s Death – Inception
As much as Inception is a fan favorite, Leo’s own performance isn’t discussed as much as is usual in his films, potentially because of how the film is considered more of a whole than an individual piece. Leo’s at his best whenever Mal (Marion Cotillard), his wife, is on screen with him. Their chemistry is fantastic and their established relationship makes for some very interesting moments. When Cobb (DiCaprio) revisits her death, the exchange is heavy, ripe with tension and drama. Even with so many great moments in such a great film, this one really stands out because it shows DiCaprio’s ability to demonstrate frailty.
7. Domestic Dispute – Revolutionary Road
I don’t love this film. In fact, I don’t like it at all. But it’s impossible to deny how amazing both Leo and Winslet are in it. There are several moments in their dysfunctional relationship that amount to insane bouts of screaming and arguing, allowing them both to really go all out on each other. There are two fights in particular that stand out as Leo’s best. One is in the living room and one is outside by their car. I won’t choose between these two because they show off such different sides of Leo’s ability, so, instead, I’ll just combine them and bravo.
6. Dinner Scene – Django Unchained
The now famous dinner scene has made its rounds throughout the public and has become a common story for many. Leo’s ability to stay in character after cutting open his hand on a smashed glass has even begun to be laughed at, exaggerated and ridiculed, but it shouldn’t take away from the power of the scene. The way he so convincingly and seamlessly switches between tones and levels of excitement is really amazing in itself; add in the broken glass and bloody hand, and you have yourself a scene that will be recognizable for decades.
5. Letting Go – Shutter Island
The really stylish and beautiful scene between Michelle Williams and DiCaprio stands out in this film as the very best. They both get to demonstrate the range of their dramatic abilities in a potent goodbye. Overall, I think it’s actually one of the weaker films on the list for Leo, but the scene is excellent and deserves to be acknowledged. His ability to flawlessly move between emotions and incorporate it into his speech is like no other. Add in the great chemistry with Williams, and the magnitude of the performance is magnified.
4. The Bear Attack – Revenant
How hard is it to get ravaged by a bear? Well to have it look and feel as real as it did, probably pretty difficult. Leo’s skin-crawling screams of pain are made all the more important by his silences in the scene, his shaking breaths and sloppy facial expressions are really captivating and make the experience feel very virtual. While there were several moments from the film itself and from Leo’s award winning performance that could have made this list, I think the amazing effects of the bear attack often overshadow Leo’s performance in the scene, so I’ve taken it upon myself to clear that up.
3. Show Me All the Blueprints – The Aviator
There’s so much to Leo’s depiction of Howard Hughes in The Aviator that it is difficult to just look at one scene, but, for me, the most powerful scene is the anxiety attack his character suffers when looking at the steering wheels and the sweeping man. Leo is brilliant in showing how his attentions are split between multiple things and how his anxiety slowly builds. His expressions and speech change dramatically throughout the scene leading to a powerful mental and physical transformation. As he is walked out repeating “show me all the blueprints” over and over again, Leo’s words and his facial expressions appear as is they come from two different people.
2. At His Mother’s Door – The Basketball Diaries
The role of Jim Carroll is a really interesting one for Leo as it is his first major starring role and he absolutely hits it out of the ballpark. The best scene happens when he knocks on his mother’s door to get money for drugs after she has made the conscious effort to shut him out in order to help him. His pleas and cries for help are enough to make even the manliest of men turn into blubbering little children. If I was a mother, I’m positive that I would never be able to get through this scene without breaking into tiny little pieces.
1. Mama Wake Up – What’s Eating Gilbert Grape
In a role that got him his first ever Academy Award nomination, the then 19-year-old DiCaprio plays Arnie, a young boy with developmental disabilities. The scene in which his mother dies and Arnie is confronted with the lifeless body is one of the most difficult scenes of his to watch. His uncanny ability to capture and maintain little mannerisms while showing so many different emotions is unbelievable. Even today, over 20 years after the film’s release, this performance from Leo is one of his best, and this single scene might just be his best ever.
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