Some of the most famous roles from the career ofLeonardo DiCaprioare him showing up as a real-life figure, typically in the starring role. A couple of his collaborations with Martin Scorsese appear on this list, with other big-name directors to boot.
Sure, there are a couple of duds near the beginning of the list that you may not have even heard of. But for the most part, you’ll recognize the majority of these titles. And if you haven’t seen the list’s upper echelon, rest assured that they’re well worth your time. All that said, this is every time Leonardo DiCaprio played a real-life figure, ranked.
9Total Eclipse
By far the worst film on the list isTotal Eclipse(1995), directed by Agnieszka Holland from a script by Christopher Hampton. Appearing as French poet Arthur Rimbaud, the actor at hand actually received flack from pundits. Sure, certain film critics like Roger Ebert championed the film upon release, and audiences were for the most part pleased with the product.
But overall, it fails to hit any sort of qualitative nail on the head, with DiCaprio’s co-star David Thewlis also coming up emotionally short as another French poet named Paul Verlaine. It’s hard to call the dud of a film the fault of those performers, as their director and screenwriter counterparts also came up short with the content. But no matter the reason,Total Eclipseis the worst film in which Leo DiCaprioplayed a real-life figure.
8The Man in the Iron Mask
Although the titular role — named Philippe Bourbon in the film, though he was unidentified in real life — was played by Leonardo DiCaprio, he actually showed up inThe Man in the Iron Mask(1998) in a dual role. He also portrayed the villain, real-life Louis XIV, King of France from 1643 to 1715. To an extent, the actor of the hour performed in admirable fashion. But he was only given so much to work with from a perspective of qualitative scriptwriting.
No one truly had room to shine, in other words. Not Jeremy Irons, not John Malkovich, not Gabriel Byrne. Not even Gérard Depardieu could make any headway in front of the camera, and that wasn’t just due to the lackluster screenwriting efforts, but also the directorial work from the same name: Randall Wallace. He wrote the script and directed the product, but still couldn’t make the overall tone ofThe Man in the Iron Maskresonate with critics at all. Nor with audiences.
Following the American law enforcement administrator J. Edgar Hoover from his participation in the 1919 Palmer Raids, the plot lasts until his involvement in the Nixon administration. And aside from Leonardo DiCaprio in the starring, titular role, another name worth noting with regard toJ. Edgar(2011) would be its director, famous Hollywood icon Clint Eastwood.
But with a 43% approval rating oncritical consensus website Rotten Tomatoes, this is far from the best film of his critically acclaimed career as a director. In fact, it could very well be the worst. Up there, at the very least. Aside from the performance of DiCaprio and others from thespians such as Naomi Watts and Armie Hammer, there isn’t too much worth writing home about here from a qualitative perspective. In the end, theJ. Edgarbiographical drama lands at number seven on the list.
6The Basketball Diaries
This underrated sports film from director Scott Kalvert also goes down as one of the more overlooked performances of DiCaprio’s career. He portrays the protagonist Jim Carroll, a high school basketball player who finds himself with a devastating addiction to heroin. Carroll wrote the autobiography of the same name from which the film is based, and it was released to generally mixed reviews from critics despite its clear overall quality.
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It’s a seriously solid sports stint from start to finish that just doesn’t get the love it deserves, nor did it upon release.The Basketball Diaries(1995) made only $2.4 million atthe worldwide box office, and it holds a 47% approval rating on the aforementioned critical consensus website. Even if this isn’t the best movie you’ll read about today, those numbers are without a doubt unwarranted. But it does feature Mark Wahlberg, so, even if you don’t resonate with its style or plot, you at least have an early performance from Marky Mark.
5This Boy’s Life
AlthoughThis Boy’s Life(1993) falls short of the upper ranks, it still marks a relatively noticeable leap in quality compared to the previous entries on the list. Here, DiCaprio portrays an American author named Tobias Wolff, nicknamed Toby, and the film itself is based on the author’s memoir of the same name from 1989. Toby’s stepfather is played by Robert De Niro, while Ellen Barkin shows up as Toby’s mother. And speaking of the cast, it’s worth noting thatThis Boy’s Lifealso marks the on-screen feature film debut of American actor Tobey Maguire.
He and DiCaprio would collaborate twice more, once withDon’s Plum(2001) and again inThe Great Gatsby(2013). But perhaps more notable are DiCaprio’s futurecollaborations with De Niro: first withMarvin’s Room(1996), and again with the upcomingKillers of the Flower Moon(2023). They all performed wonderfully inThis Boy’s Life, with shining dynamics that led the quality of its emotional journey to new heights.
4The Revenant
Off the bat, it’s worth noting thatThe Revenant(2015) by Alejandro Gonzales Iñárritu finally garnered Leonardo DiCaprio his long sought after Best Actor win at the Academy Awards. He played American frontiersman Hugh Glass in a riveting, real-life story that was embellished for the sake of blockbuster spectacles. But relinquishing a bit of verisimilitude for a poignant performance and stunning camerawork was well worth it in the end.
Of course, many fans of DiCaprio felt his win was long overdue, and that he should’ve in fact won the award for an earlier performance in his career. He had been nominated for Best Actor three times before this entry was released, with another nod for Best Supporting Actor to boot. That shouldn’t take away from his performance here inThe Revenant, though. He drove the film’s quality through and through, ultimately landing it here at number four.
3The Aviator
Marking his firstcollaboration with Martin Scorseseto appear on the list,The Aviator(2004) was also his second time partnering with the American director overall. Their first outing together wasGangs of New York(2002), a period crime drama co-starring Daniel-Day Lewis. And with all respect to DiCaprio, there’s no doubt who stood out as the marquee performer in that particular project. But thanks toThe Aviator, the director-actor duo returned in grand fashion, with DiCaprio picking up an Academy Award nomination for Best Actor.
Well-warranted too, even if he came up short in the end to Jamie Foxx as the titular character inRay(2004). But as American aviator Howard Hughes, the actor at hand ran the gamut of emotion from start to finish. Hughes had a severe case of OCD all throughout his life, and DiCaprio depicted the disorder to an absolute tee. His efforts ultimately propelled the quality ofThe Aviatornot just to widespread critical acclaim, but also to the third spot on this list.
2The Wolf of Wall Street
Unforgettable plot points, memorable one-liners, and indelible performances — there are endless reasons whyThe Wolf of Wall Street(2013) lands in the penultimate spot. It features acting efforts from the likes of Jonah Hill, Margot Robbie, Matthew McConaughey, and of course Leonardo DiCaprio. The man of the hour portrays American stockbroker Jordan Belfort here inThe Wolf of Wall Street, and this may be the single most fan-favorite role ofhis acclaimed career.
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DiCaprio hits all of Belfort’s idiosyncratic nails on their head, with his work in the Quaaludes scene representing that notion entirely. The overall picture of Belfort attempting to enter his Lamborghini while practically paralytic goes down among the funniest efforts of DiCaprio’s career, and of course, he shares tremendous on-screen chemistry with all the aforementioned thespians. While he came up short for Best Actor at the Academy Awards here inThe Wolf of Wall Street, the movie nonetheless lands at number two.
1Catch Me If You Can
With the overall product having been directed by Steven Spielberg, it’s no wonder thatCatch Me If You Can(2002) turned out to be one of the greatest films from everyone involved. Of course, that includes the man of the hour in Leonardo DiCaprio, who played the protagonist Frank Abagnale Jr. here in the number one pick.
He shares tremendous chemistry with his co-star Tom Hanks, who plays Carl Hanratty — an FBI agent who himself is based on a real-life figure of a different name: Joseph Shea. The character is tasked with tracking down Abagnale, who executes cons worth millions of dollars in total by posing as esteemed figures of various occupations. And although the historical accuracy is commonly in dispute, there should be no doubt in the world thatCatch Me If You Cannonetheless makes for a fantastic film.
