When I met my wife in 2008, she told me after a few months that “Tom Cruise is your man crush” because so many movies I enjoyed rewatching (as evidenced by my DVD collection at the time) featured Cruise as the lead. Undoubtedly, through the first half of my life, replays of Top Gun (my #2 all-time favorite movie), Cocktail, and A Few Good Men confirmed that Cruise was my favorite actor. In the mid-2000s, though, there was a shift in my movie tastes and with it the beginning of a shift toward a new favorite actor. Cruise eventually moved to second place to make way for Leonardo DiCaprio. Here are the five films that best describe why:
5. Shutter Island – Honorable mention to his Oscar-winning turn in The Revenant and his work with Christopher Nolan’s Inception, but Leo’s 2010 collaboration with Martin Scorsese is in my opinion his most underrated role. I’m a sucker for a movie about multiple identities. I switched majors in college from biology to psychology because I find the mind to be the most fascinating piece of the human existence. From a movie-loving standpoint, I think the challenge of playing two roles in one is daunting and I greatly appreciate those who perform it well; to me it’s the film equivalent of hitting the game-winning shot in a playoff game. Edward Norton, for instance, will always get a gold star from me for both Primal Fear and Fight Club. Leo similarly stepped up to the plate and knocked it out of the park in Shutter Island.
As proven in his 2006 performance in a Scorsese film to be discussed momentarily, Leo does an excellent job of portraying a man full of psychological tumult, walking the fine line between utterly stressed out but holding together by a thread and the bottom of his mind dropping out leading to insanity. He never crosses that line as Billy Costigan, but he does here as Teddy Daniels.
4. Titanic – C’mon dude. If you tell me that Titanic isn’t a ridiculously rewatchable movie and that Jack Dawson is a guy that, if you met him in real life, you wouldn’t go out of your way to help find his footing because of the potential you see in him as a person, I’m calling you a liar, Mean Gene.
Youngsters today would scoff at the notion of rewatching this like I did in the late 1990s, ejecting tape #1 to make way for #2 (the film’s epic length required it be a two-VHS set), but that’s what I did. I believe it was also the first movie that I saw in the theater more than twice. 13 year old me went to see it because of the Titanic sinking appeal, wanting to see the tragic story told in school manifest on the big screen, but that same 13 year old me went back to the theater again and the version of me at every age since has typically watched at least some of it each time Titanic was on TV because of the strength of the story, anchored by Leo’s Jack, the everyman who one-ups the system and saves the girl. Forbidden love ending in tragedy is timeless.
3. Catch Me If You Can – This was the game-changing Leo movie for me. As a child of the 1990s, I was often annoyed by female fascination with DiCaprio as Jack Dawson, so there was a bit of a stigma with that teenage association that Leo had to shed to work his way onto his current place in my actor hierarchy. When I was in college, a typical Time Warner Cable customer service debacle led to six months of free service, including HBO, during a time when this movie about young bank fraud expert, Frank Abignale Jr., was replaying consistently. The film is a blast to rewatch, flowing effortlessly across its run-time, so rewatch it I did. It would be very accurate to say I’ve seen it 25 times at least across the past two decades and it may not be a stretch to say I’ve seen at least bits and pieces 50 times or more.
Tom Hanks and Christopher Walken are excellent too, but it’s a DiCaprio movie through and through. He maintains a youthful and rather relatable charm, even as he makes his way in the world through increasingly cunning deceit. It is an odd type of anti-hero role, but Leo owns it in such a way that reveals the true silliness in looking at the world through a black-and-white lens. His hero-worship of his flawed father (Walken) informs some of the more powerfully emotional scenes, all of which add the kind of depth to Leo’s Frank Jr. that make you root for him.
2. The Wolf of Wall Street – Perhaps the most ludicrous three hours in film lore, spearheaded by the story of a guy who lived limitlessly at the expense of others. I mean, it’s almost weird to say you love a movie about one of my lifetime’s greatest financial villains, a true pirate of the modern age. Villains are more interesting, though, in an ironic sort of way. Scorsese illustrated that point well with Kyle Chandler’s protagonist character taking the subway home after getting Leo’s Jordan Belfort put away for three years and forcing him to spill the beans on Wall Street’s most illustrious. What do you get for arresting a notorious economic criminal and archetype of corruption in the late 20th century that continues to this day in various ways under our noses? Underappreciated financially, that’s for sure.
It’s dark comedy at its finest. Leo is part Gordon Gekko and part Jim Carrey, and it’s hard not to laugh at the insanity of all his vices and debauchery. Certainly, cheers to the supporting cast because they’re iconic too; Margot Robbie splashes onto the scene here and seems poised to become an all-time icon now, Matthew McConaughey has never been better (and he’s only in the movie for like three scenes and less than fifteen minutes), Jonah Hill is unreal as Belfort’s #2, and even Rob Reiner (the director of several classic rewatchables) as Jordan’s dad knocks it out of the park. But it’s Leo’s vehicle and he drives it like a lunatic to probably his best performance.
1. The Departed – After rewatching Catch Me If You Can so many times, the stage was set for Leo’s performance as an undercover cop trying to take down Irish mob moss, Frank Costello, to take him definitively out of the “Titanic guy” spot in my mind and move him squarely into the territory of being the actor whose career I would follow as an adult like someone would the career of Tom Hanks had their formative years been the 1980s.
It was a bit of a right place, right time scenario for Leo. The innocence of youth was still one of his hallmark traits and part of his on-screen likability, making it easy to buy into him as the smart kid who winds up dropped into a volatile situation, struggles mightily with the anxiety of it, and occasionally allows extreme bursts of anger to erupt. His plea to the psychiatrist for something to chill him out served as the scene that made me an unabashed Leo fan, apt in the years since to say, “Awesome, DiCaprio has a new movie coming out.” Considering that he shares the screen with Nicholson and gets strong competition for movie MVP from Matt Damon and Mark Wahlberg (whose show-stealing attempt is admirable) and further considering that he was acting in a really high profile and high pressure Scorsese mob film, Leo delivering arguably his career-altering performance was incredibly impressive.