Nathan is a film critic and aspiring author with a true passion for the film industry who hopes his writings will help launch his career.
Leo started as a kid star and grew into one of the most talented actors in Hollywood. He specializes in characters with broken minds and terrorized hearts, and he makes the audience feel every moment. But every actor has their bad films. What's Leo's? Below I have listed the top five best and top five worst of Leo's films. As always, I have included a complete filmography with my ratings of each film.
Best #1: The Revenant (2015)
The Revenant is not only one of the most emotionally taxing films made in a long time, it also has some of the most intense sequences. One thing I love about director Alejandro G. Iñárritu is the fact that he has mastered the art of single continuous shot sequences. In fact, the first battle between the settlers and the Native Americans, the bear attack, and the final face off were just a few of the one continuous shot sequences. Leonardo DiCaprio is at his best in this film, in which he won his first Oscar for Best Actor. He definitely deserved it. I give the film a 4 out of 4.
Best #2: Shutter Island (2010)
Shutter Island is the type of film that you really need to pay attention to. It takes place in an asylum for the criminally insane, which is on Shutter Island. Leo DiCaprio and Mark Ruffalo play agents who have come to the island to investigate the disappearance of a patient. The film takes interesting and deep twists and turns, and pretty soon you find out that nothing is as it seems. The acting is fantastic and the directing by Martin Scorsese is spectacular. I give the film a 4 out of 4.
Best #3: What's Eating Gilbert Grape? (1993)
In What's Eating Gilbert Grape?, Leo plays a mentally disabled young man who relies on his brother Gilbert, played by Johnny Depp, to take care of him. This was Leo's first major role and he certainly deserved an Oscar for his performance, but unfortunately lost out to Tommy Lee Jones for The Fugitive. I give What's Eating Gilbert Grape a 4 out of 4.
Best #4: The Departed (2008)
The Departed is another film that you really have to pay attention to. It's almost Hitchcockian in a way but at the same time it's a gritty, edgy Scorsese thriller. Leo has done several films with Scorsese, including the aforementioned Shutter Island, but The Departed definitely needed to make the Top 5 Best List simply for how much it makes you think and makes you just as paranoid as the characters on-screen. You never know who to trust or who the real villain is until the very last moment. I give the film a 4 out of 4.
Best #5: Once Upon a Time in Hollywood (2019)
I can't help but admire Quentin Tarantino. The man has delivered one masterpiece after another, never pandering to the cliche that Hollywood has become. He does the movies he wants to do how he wants to do them and is unapologetic about it. Each one is always wildly different from the others too. He's almost like a whole new director each time.
That being said, he has done two films in particular that are similar in one sense: they're "what if" films. In other words, they take true stories and turn them upside down, making a whole new chain of events that could have happened. One of those films is Inglourious Basterds. The other is Once Upon a Time in Hollywood.
Obviously, from the title Once Upon a Time... you can deduce that this is a fantasy story. Tarantino actually did include things that really happened, but the ultimate payoff is wildly different from the true events. That's okay. This was never meant to be a biography or a true story. It was meant to get us wondering what could have— or even should have— happened.
The film follows Rick Dalton, an actor who believes his career is close to an end. His show was recently cancelled because he wanted to break into films and the film industry spit him back out. All he has to keep him going is his best friend and former stunt double Cliff Booth.
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The film focuses on Rick and Cliff, but also touches base on Charlie Manson's cult. We only see Charlie himself a couple times, but the cult is literally everywhere. It makes one wonder just how many people were actually involved with him.
The star of the film was Brad Pitt. He not only had some of the funniest lines in the film, but he also had some of the best moments. His chemistry with Leo DiCaprio was perfection and he stole the spotlight in every scene he was in. Leo has a knack for characters who are disturbed or insecure.
In this case, Rick Dalton was insecure. One could actually write an entire article on Leo's mannerisms alone in this film, from Rick's off-camera stutter to his self-deprecation, he was an 100% relatable character. Margot Robbie didn't have a huge part, so don't go into the film expecting a lot from her character. On the plus side, if a bio flick is made solely about Sharon Tate, give Margot the role!
In conclusion, this was a terrific film in full-on terrific Tarantino fashion that once again entertained while making us ask the questions no one's asked in 50 years. I give the film a 4 out of 4.
And now we come to the dreaded Worst section. Some of the following films are really not great at all and some were good but needed some improvement. There are a few on this list that aren't exactly bad per se but were just lesser than what we're used to seeing Leo do. Here are my picks for the top 5 worst (or lesser) of Leonardo DiCaprio's films.
Worst #1: Critters 3 (1991)
Now, you do have to give the kid some credit. This was Leo's first film job and he did his part well. The film itself, however, was just cheesy and overly ridiculous. Oh, well. That's early 90s horrors for you. At least Leo would go on to redeem himself in This Boy's Life just a few years later. I give Critters 3 a 1.5 out of 4.
Worst #2: Poison Ivy (1992)
Poison Ivy could have been a decent thriller, but the script was just not that great. What sounded like an intriguing thriller actually turned out to be exploitative and unremarkable. The acting wasn't too bad, but it wasn't great either. Overall, it's just an average film that needed a lot of work before being released to the public. I give the film a 2 out of 4.
Worst #3: Romeo + Juliet (1996)
There have been several modern movies based on Shakespearean plays, but I can't think of any other film that actually used the dialogue from the play itself word-for-word. It was an interesting idea, but it ultimately failed. Mixing Shakespeare's beautiful yet tragic dialogue with a modern brutish society just did not mix well. Leo gave a terrific performance but the clash of cultures killed the film. I give it a 2 out of 4.
Worst #4: Body of Lies (2008)
Body of Lies was a film that I had high hopes for. The casting was intriguing, the story seemed to be quite revealing, but the film itself turned out to be a bit of a let down. Instead of educating us on what really goes on within the CIA or what happened on a real mission, the film mixed outrageous circumstances with a reality-based plot which ultimately hurt the film. It almost felt like it tried to be an American version of James Bond, only much more intense and brutal. I give the film a 2.5 out of 4.
Worst #5: Revolutionary Road (2008)
Revolutionary Road had some incredible performances and it was wonderful to see Leonardo DiCaprio and Kate Winslet together on-screen again, but the film suffered mainly because of the plot. The whole film is basically one argument after another and another and after 30 minutes, you're wondering if there's ever going to be a resolution. It could have been such an incredible and emotional film but the audience was too busy trying to figure out what the point was. I give the film a 2.5 out of 4.
- Critters 3 - 1.5 out of 4
- Poison Ivy - 2 out of 4
- This Boy's Life - 3.5 out of 4
- What's Eating Gilbert Grape - 4 out of 4
- The Quick and the Dead - 3 out of 4
- The Basketball Diaries - 3 out of 4
- Total Eclipse - 3.5 out of 4
- Romeo + Juliet - 2 out of 4
- Marvin's Room - 4 out of 4
- Titanic - 4 out of 4
- The Man in the Iron Mask - 4 out of 4
- Celebrity - 3 out of 4
- The Beach - 3.5 out of 4
- Don's Plum - 3 out of 4
- Gangs of New York - 4 out of 4
- Catch Me if You Can - 4 out of 4
- The Aviator - 4 out of 4
- The Departed - 4 out of 4
- Blood Diamond - 4 out of 4
- Body of Lies - 2.5 out of 4
- Revolutionary Road - 2.5 out of 4
- Shutter Island - 4 out of 4
- Inception - 4 out of 4
- J. Edgar - 3 out of 4
- Django Unchained - 4 out of 4
- The Great Gatsby - 3 out of 4
- The Wolf of Wall Street - 4 out of 4
- The Revenant - 4 out of 4
- Once Upon a Time in Hollywood - 4 out of 4
- Don't Look Up -
Leonardo DiCaprio has had a successful and dynamic career. He's a kind and humble person, which is something you don't see in many big-name Hollywood actors anymore. He's certainly a gem, one we hope will continue dazzling us for many years to come.
© 2016 Nathan Jasper
Pat Mills from East Chicago, Indiana on October 18, 2017:
Good lists, though I'm not as down on Revolutionary Road as you are. The Wolf Of Wall Street would definitely get a place among the very best for me.