December 10, 2021
I’m going to go out on a limb and guarantee that as long as I continue to do this little hobby of mine, that this will be the only post that will include any reference to the 1980s television show Growing Pains. If you were hoping for a Kirk Cameron career retrospective at some point, I’m sorry, but you’ll have to look elsewhere. Or if I do end up writing about that topic, maybe it’s time to shut it down (in more ways than one.) OK, where was I? Oh, yes.
In case you didn’t know it, Leonardo DiCaprio got an early break on that 1980s sitcom, playing a homeless boy who comes to live with the Seaver family. It was one of those classic sitcom movies where they try to bring in a new character to spice things up when the show is on its last legs. Remember cousin Oliver on The Brady Bunch? Same strategy. DiCaprio joined the show in its seventh and final season, right before the time of death was declared on Growing Pains. That’s ok, though – we quickly saw that he had bigger things planned with his career.
Leo has now been acting for over thirty years, building an impressive resume of roles and performances, including six Oscar nominations, with one win. The film that delivered his only Oscar, The Revenant, was not one of my favorites and won’t be on my list of my top ten movies he has made. I thought his performance was excellent, and despite beautiful cinematography, I found the picture itself a little boring for my taste. I think the Oscar win was more of a career recognition / “It’s time for Leo’s Oscar” than an award for that specific film. That being said, throughout his career, he has made very interesting choices in the roles he takes, focusing on original stories and not franchise / IP movies. Despite those risks, he rarely makes a bad film.
What is also impressive is the variety of top tier directors he has worked with throughout his career – check out this list, most of whom are Oscar winners: Ridley Scott, Christopher Nolan, Clint Eastwood, Baz Luhrmann, Sam Raimi, James Cameron, Sam Mendes, Danny Boyle, Alejandro Iñárritu, Quentin Tarantino, Steven Spielberg, and his most famous collaborator, Martin Scorsese. The two are in production on their sixth picture together, Killers of the Flower Moon, which will be released next year. In the meantime, later this month we’ll see Don’t Look Up, Leo’s first film with Adam McKay, the Oscar-winning writer and director of The Big Short and Vice. The movie is a dark comedy with a star-studded cast led by DiCaprio and Jennifer Lawrence as astronomers tasked with warning the world about a comet that will destroy the planet. You can watch Don’t Look Up on Netflix on December 24th (Merry Christmas – the world is ending. Feels about right for the pandemic world we’re still living in). But for now, we’re going to take a look at my top ten Leo movies. We’re starting with the film that earned him his first Oscar nomination and showed the world that we were seeing an incredibly talented actor with a long career ahead of him.
10. What’s Eating Gilbert Grape? (1993)
I’ve always known about this film, but had never seen it. There was no particular reason – I just never got around to it. When I set out to write this piece, I decided to revisit as many of Leo’s movies as I could, to do a full examination of his career and decide on my top ten. His career can be defined by two timeframes – the first ten years when he was largely playing teenagers / young adults, including the role that launched him into superstardom (which we’ll get to next week), and the latter part of his career when he took on more adult roles, including his most recent role as someone facing a midlife career crisis.
Considering how many child actors burn out at some point, it’s quite impressive that he has continued to work consistently since the early 1990s. In 1993, he was hand-picked by Robert De Niro to play opposite him in This Boy’s Life, about a young boy stuck with an abusive stepfather. De Niro is a menace as the stepfather, and DiCaprio, in his first major film role, showed that he had the acting chops to play opposite such a talented actor. Later that year, we saw DiCaprio in a completely different role.
When I finally got around to watching What’s Eating Gilbert Grape?, I had this strange experience. Throughout the movie, I knew that I was watching Leo, but I kept saying to myself, “I can’t believe that’s DiCaprio!” It’s not just because he was only 18 at the time – you can still tell it’s him. It was because the performance is so atypical from anything else we’ve seen from him. He played Arnie, the intellectually disabled brother of Gilbert, played by Johnny Depp. Gilbert is juggling a lot in his life in a small town – taking care of his brother, his two sisters, his homebound overweight mother, holding down a job at the local supermarket, and carrying on an affair with a married customer who frequently visits him at work. Depp is great in the role, during his heyday of strong performances, but Leo is a revelation. He plays Arnie with a sweetness and sadness as he can’t help but get in trouble, including frequently climbing the town’s water tower, much to the police’s frustration. DiCaprio received an Oscar nomination for Best Supporting Actor, losing to Tommy Lee Jones for The Fugitive. At that stage of his career, it wasn’t important to get the win – the nomination gave him significant recognition, which put him on the map.
9. Revolutionary Road (2008)
When the details of this film were announced, much was made about the reunion of its two leading actors, DiCaprio and Kate Winslet, who previously starred in a little movie about a boat that you probably remember. But this was decidedly not a whirlwind romance, despite the actors playing a married couple. I admire the two actors for trying something completely different in their first film together since that blockbuster a decade earlier. It shouldn’t have been a surprise, since they are two of the best actors working today.
Revolutionary Road is based on a 1961 novel by Richard Yates, and is considered a defining novel about the suburban lifestyle of the 1950s. DiCaprio plays an aspiring sales professional, trying to move up the career ladder and support his wife, played by Winslet, and their two children. They met and married when they were young, quickly having kids and facing the inevitable crisis of “Where is my life going?” Both DiCaprio and Winslet play these roles perfectly, demonstrating that precarious time in life when you are faced with real-world adult problems and potentially seeing your life’s dreams slipping away.
The couple has very few friends, but interact with their neighbors and their adult son, who was just released from a psychiatric hospital. The son is played by Michael Shannon (an underrated actor who received an Oscar nomination for his performance) and he sees right through the façade that the couple display as a “perfect, happy couple.” Revolutionary Road is a very different movie for DiCaprio, Winslet, and director Sam Mendes (the husband of Winslet at the time), and as a domestic drama exploring themes of happiness and the definition of success, it’s very well done.
8. The Aviator (2004)
I’ve written many times that biopics are tricky. If you try to aim too high and tell the full “cradle to grave” story, you can gloss over a lot of events to cram everything into a two hour movie. I tend to prefer biopics that focus on a few specific events of a character and not go too deep across their whole life. While Leo has played a number of real-life characters, including our next two films, I think he has only done two true biopics. The first one was The Aviator, the Martin Scorsese-directed portrait of Howard Hughes, the aviation pioneer and film producer, who poured every nickel of his company’s profits into his passions and obsessions. I won’t spend too much time on his second venture, the disappointing J. Edgar, the 2011 film about FBI director J. Edgar Hoover, directed by Clint Eastwood. That movie was a bit of a slog, with my main memory being Leo buried in a bunch of makeup hamming it up in a performance that was kind of “over the top.”
On the contrary, The Aviator finds DiCaprio portraying Hughes’ radical transformation from a visionary with bright ideas about the future to someone who is completely overcome with his obsessive-compulsive disorder, jeopardizing his future and his health. DiCaprio is magnificent in this role, never losing the paranoia and idiosyncrasies of his condition, all while pushing himself and his employees forward on his ventures. Ironically, his obsession to detail is what made his film projects and his airplane designs so effective, even if they went wildly over budget and were delayed extensively due to his constant tinkering.
Scorsese directed a fantastic film led by DiCaprio’s performance and a strong supporting cast, including Alan Alda, Alec Baldwin, John C. Reilly, and in an Oscar-winning performance, Cate Blanchett as Katherine Hepburn, who was Hughes’ partner and friend during his heyday. This was a very tricky role to play, as Hepburn is considered one of Hollywood’s legends who (obviously) was on screen for decades. So, we naturally had a wealth of comparisons to make to Blanchett’s performance, which comes across as genuine and not in any way cartoonish, which would have been a risk with a lesser actress. While the film does have a few of the tropes you see in a biopic, the strength of Leo’s portrayal of Hughes makes it a worthwhile watch.
7. Catch Me If You Can (2002)
Shortly before Leo partnered up with Martin Scorsese for the first time with Gangs of New York (a decent movie with a phenomenal Daniel Day-Lewis performance), he teamed up with Steven Spielberg, in their only collaboration to date, Catch Me If You Can. He portrayed Frank Abagnale, Jr., a con man who took on numerous identities in the 1960s and maintained his lifestyle through a check forging scheme that netted him quite a bundle of money. He was eventually brought down by an FBI agent, played by Tom Hanks. I wrote about this film as part of my look at Steven Spielberg’s best movies, noting that it was heavily influenced by the family dynamic that Abagnale experienced when his parents divorced. In addition to Spielberg’s talents as a master storyteller, what makes this one such a fun watch for me is the dynamic between DiCaprio and Hanks.
It’s kind of ironic that at this stage in Leo’s career, he was trying to move past the roles of teenager / young adult, and he plays someone who started his check forging scheme when he was just 15. While DiCaprio has the youthful look of someone that age, the schemes that Abagnale was running were quite sophisticated – he posed as a pilot for Pan Am Airlines, a doctor, and a lawyer. Along the way, he dupes many people with his charms and kind words to get what he wants, all while banking more money to maintain his lifestyle. And anytime he starts to feel the FBI closing in, or his lies starting to fall apart, he packs up his suitcase of money and forging equipment and runs for a new city. Hanks is the Wil E. Coyote to Leo’s Roadrunner, always just a little too late to catch him, or not realizing the person he is looking for is right in front of him. While I found Hanks’s accent a little annoying (I still don’t understand accent decisions from filmmakers), he’s great in this role and a perfect foil for Leo’s criminal. In another actor’s hands, I’m not sure how well this movie would have worked. It takes a lot of charisma to charm not just the victims of his crimes, but to make a career thief likable to the audience too. A good old-fashioned crime caper comedy from three of the best – Spielberg, Hanks and Leo.
6. The Wolf of Wall Street (2013)
Of all of the movies on my list, I had the hardest time figuring out where to rank this one. I know I’m one for hyperbole in my writing style, but this has to be the biggest disconnect between the impressive performance of an actor and the disgracefulness of the character he is playing. DiCaprio plays Jordan Belfort, a disgraced former stockbroker who started with the goal of making money on Wall Street and ended up serving time in prison for committing many crimes during his career. Now, we’ve seen some pretty nasty Wall Street characters over the years, but Belfort (a real person) makes Gordon Gekko (a fictional character in Wall Street) look like a saint. Belfort’s actions give new meaning to the word “deplorable.” Throughout the movie, we see him (and his band of idiots) not only commit crimes, but abuse drugs, treat women in the most horrible ways possible, and basically demonstrate incredibly bad behavior. So, why on Earth did people like this movie, including the Academy, which gave it five Oscar nominations, and the Golden Globes, which gave DiCaprio an award for Best Actor? Well, it’s a dark comedy, with emphasis on the word “dark”, directed by Martin Scorsese, a master storyteller.
I had a hard time figuring out where to rank this movie because there are parts of this film that are fantastic and hysterical, including Jonah Hill as DiCaprio’s right hand idiot, Margot Robbie (in a breakout role) as Belfort’s second wife, Rob Reiner as his father, and Matthew McConaughey as a mentor in a small role early in the movie. When we see the lengths that Belfort and his firm will go to in order to make more money (there is never enough, as we see as the story progresses), aspects of it are pretty funny. The way Leo inhabits the mannerisms of a deplorable scumbag selling stocks to unsuspecting customers, and rallying his troops at employee meetings demonstrate acting brilliance.
What left me a little lagging in recently rewatching the movie is that sometimes there can be “too much” of something in a film. As much as I love Scorsese, I think he could have cut some of the scenes where we see how bad the behavior was among Belfort and his cronies – we get it, they’re deplorable assholes. We got it the first ten times. You can cut out the next five examples. And maybe, we could have cut down on the uses of the word “f*ck” throughout the picture – in fact, The Wolf of Wall Street set the record for most uses of the word in film history. A dubious record, for sure.
Don’t get me wrong – I’m by no means a movie prude, but there were times where I thought the crudeness went overboard. I had a similar problem with Django Unchained, the Quentin Tarantino revenge film about a slave (Jamie Foxx) who gains his freedom and goes on a mission to rescue his wife from a nasty plantation owner, played by DiCaprio. While I admire Leo’s portrayal as the worst kind of human being, the violence and ugliness of the movie was too much for me to “recommend.” So, as much as I love the performance from Leo in The Wolf of Wall Street, it fell just short of making my top five. If you decide to check this one out because you like dark comedies and are not easily offended, buyer beware – you might need earmuffs (and a blindfold) a few times.
That’s all for this week. I hope you enjoyed part one of my look at one of the best actors working today. I’ll be back next week for part two and my five favorite films from Leonardo DiCaprio, including one of the biggest movies of all time, two very different crime movies, a suspenseful thriller, and one of my favorite movies of the last ten years. Thanks for reading and if you’d like to be notified of future posts, you can subscribe here.