Entertainment <\/p>\n
A version of this story appeared in Esquire\u2019s entertainment newsletter, t<\/em>he Cliff-Hanger<\/em>. Sign up here<\/a> to receive weekly criticism of the movie or television show of the moment shipped directly to your in-box.<\/em><\/p>\n Are you sitting down? You might want to grab a chair, because I almost passed out after reading that this year is Inception<\/a><\/em>\u2019s 15th anniversary. It\u2019s not easy to make a guy in his early 30s like me feel he\u2019s getting older [Editor\u2019s note: Speak for yourself, Josh<\/em>], but that one hit me right in the gut.<\/p>\n It\u2019s no secret that Inception <\/em>is an incredibly important film in the modern movie canon, not just for the ascending careers of both Leonardo DiCaprio<\/a> and Christopher Nolan<\/a> but for its impact on every brainy sci-fi<\/a> concept film<\/a> thereafter. We may have never suffered from our multiverse storytelling affliction if not for Inception<\/em>\u2019s journey through multiple layers of dreams. And without Hans Zimmer\u2019s booming score, trailers that began with cheery narrators explaining exactly what the movie is about might not have gone the way of the dinosaurs. I\u2019m not the kind of Nolan-obsessed Letterboxd bro to put Inception <\/em>in my top four films, but it\u2019s easily one of DiCaprio\u2019s most iconic roles.<\/p>\n The actor has a new movie out next month titled One Battle After Another<\/em>. It\u2019s his first with director Paul Thomas Anderson<\/a>, who claims that the film full of car chases, guns, and high-energy camera work is his first true action flick. Of course, it wouldn\u2019t be a P.T. Anderson joint if it wasn\u2019t also about generational trauma. DiCaprio and Anderson discuss One Battle After Another <\/em>in Esquire\u2019s latest cover story,<\/a> wherein the actor says that the inspiration came from how creatives of his age are \u201cliving in a completely different world than the next generation.\u201d That disconnect is at the heart of their new movie, out in theaters September 26. <\/p>\n So in the spirit of Esquire\u2019s cover story\u2014and Inception<\/em>\u2019s 15-year anniversary\u2014it felt right to look back on the five moments in Leonardo DiCaprio\u2019s career that made him, well, Leonardo DiCaprio.<\/p>\n The world was largely introduced to DiCaprio as a child actor in What\u2019s Eating Gilbert Grape (1993)<\/em>, but audiences didn\u2019t fall in love with the actor as a young heartthrob until Romeo + Juliet<\/em>. DiCaprio was 21 years old when he linked with Baz Luhrmann<\/a> and Claire Danes on this reimagined Shakespeare story, and his acting in this modern adaptation doesn\u2019t let up for a second. <\/p>\n Remember the scene where he looks at Juliet from the other side of the fish tank? Iconic. Plus, playing Romeo certainly helped him win his role in Titanic <\/em>just one year later. I\u2019ll never forget the interview DiCaprio did at the time when he said, \u201cI want to get to a place where I\u2019m just known as a really good actor who takes good choices.\u201d If anything, the slip-up of takes\/makes only proved just how young and earnest he really was.<\/p>\n There\u2019s something perfect about DiCaprio\u2019s rambunctiousness in Catch Me If You Can <\/em>paired with the more traditional Hollywood sensibility of Tom Hanks trying to pin him down. It\u2019s as if the plot of this inventive con man versus the seasoned detective was actually about the previous generation of actors looking at this young kid who charms his way into winning any role\u2014and still respecting the hell out of him for it.<\/p>\n When DiCaprio revealed in Esquire\u2019s cover story that his own regret throughout his career so far is that he turned down Boogie Nights <\/em>to work on Titanic<\/em>, he didn\u2019t mean that he wished he worked on Boogie Nights <\/em>instead of Titanic\u2014<\/em>he meant that he wished he figured out how to do both. That\u2019s how hungry and gifted DiCaprio already was at the turn of the century.<\/p>\n Of all the exceptional DiCaprio roles in the early 2000s that featured the actor spending the entire runtime of the film absolutely losing his mind\u2014The Departed, Shutter Island, Revolutionary Road<\/em>, and J. Edgar <\/em>among them\u2014The Aviator\u2019s <\/em>story of film producer and pilot Howard Hughes easily takes the cake. (As much as I love DiCaprio\u2019s turn in The Departed<\/em>, it\u2019s more of an ensemble success.)<\/p>\n DiCaprio would probably agree. According to the actor, he rewatches The Aviator <\/em>more than any of his other movies. \u201cIt was such a special moment to me,\u201d DiCaprio says in Esquire\u2019s cover story<\/a>. \u201cI had worked with Marty [Scorsese] on Gangs of New York, <\/em>and I\u2019d been toting around a book on Howard Hughes for ten years. \u2026 I was thirty. It was the first time as an actor I got to feel implicitly part of the production, rather than just an actor hired to play a role. I felt responsible in a whole new way. I\u2019ve always felt proud and connected to that film as such a key part of my growing up in this industry and taking on a role of a real collaborator for the first time.\u201d<\/p>\n DiCaprio may have won his first Academy Award for Best Actor for The Revenant, <\/em>but it\u2019s my opinion (and that of many others) that he should have won it for The Wolf of Wall Street<\/em> two years earlier. <\/em>It was his fifth film in collaboration with Martin Scorsese, and the two of them were displaying their full sets of skills. <\/p>\n And no shade to Matthew McConaughey\u2019s victory for Dallas Buyers Club<\/em>, but DiCaprio is an absolute force in this full-throttle biopic of stock-market fraudster Jordan Belfort. No one was more equipped to crawl to their car in a drugged-out panic than the guy who played countless deranged megalomaniacs in the aughts. Plus, in his characterization of a con man disguised as a master salesman, there\u2019s a hint of Catch Me If You Can<\/em>\u2019s Frank Abagnale Jr., all grown up.<\/p>\n It\u2019s a shame that Killers of the Flower Moon<\/a> <\/em>(2023) ended up losing money at the box office\u2014that near four-hour runtime probably didn\u2019t help\u2014because it\u2019s such an important film in this stage of DiCaprio\u2019s career. Still, I\u2019d argue that he transitioned into a Mount Rushmore figure (of the greatest living actors, of course) four years earlier in Quentin Tarantino\u2019s Once Upon a Time… in Hollywood<\/a><\/em>. <\/p>\n The plot is just too perfect. DiCaprio plays a washed-up actor stuck filming movies overseas despite the fact that he\u2019s one of the biggest actors on the planet in real life. After performing a little bit of revisionist history by fighting off Charlie Manson\u2019s followers and saving Sharon Tate from murder, he\u2019s metaphorically \u201caccepted\u201d by Hollywood when she invites him in for a drink. It\u2019s an insane ending, for sure, but it was proof that DiCaprio\u2019s talents will go down in Hollywood\u2019s history books.<\/p>\n<\/div>\n
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\nRomeo + Juliet<\/em> (1996)<\/h2>\n
Catch Me If You Can <\/em>(2002)<\/h2>\n
The Aviator <\/em>(2004)<\/h2>\n
The Wolf of Wall Street <\/em>(2013)<\/h2>\n
Once Upon a Time… in Hollywood<\/em> (2019)<\/h2>\n