Leonardo DiCaprio is one of our generation’s greatest actors, and if he’s popping up in a film, chances are it’ll be a bit good - he’s a safe pair of hands, basically. But which pair of his hands is safest? Certainly not a question that makes sense, there, but one I think you understand all the same.
Look, what I’m trying to ascertain is: which of Leo’s films is the best? How do they order in terms of quality? To find out, I looked to Metacritic, because if it were up to me, we’d have Critters 3 up top (a film so ‘bad’ that it doesn’t even have a Metascore).
So here they are, from worst ta best:
Disclaimer: I have only included films that star DiCaprio as an actor, so put down that rolling pin
Here’s Leo, two years before he hit the big time with Titanic, doing a poet and getting involved in a forbidden romance, like you do. All based on a true story too, much like Titanic.
“Unfortunately, the mad romanticism of Rimbaud’s exploits has been made to look preposterous here, despite a cast that should have been magnetic in its own right.” - Janet Maslin, The New York Times
DiCaprio using a secret map to find a hidden beach - sounds boring, but isn’t really. There’s even a computer game bit. The ‘90s eh? ¯\_(ツ)_/¯
“The opening reels here promise something big, but the movie settles for a sour, predetermined funk – Lord of the Flies as imagined by a Nintendo junkie.” - Robert Horton, Film.com
The Basketball Diaries
DiCaprio plays a basketball playing poet, but then ruins it with heroin. Heroin, is not conducive to playing a good game of basketball - really hard to get it in the net.
“It’s more of a pastiche, a montage of brutality, a slow descent into Dante’s Inferno until we reach the subbasement of a boy’s soul.” - John Petrakis, Chicago Tribune
The Man in the Iron Mask
This film is the famous story about a man in an iron mask, or more specifically, the iron mask. But who is it under there? Well, to tell you would be to spoil the film, and I only do that if you’ve personally wronged me in some way - if that’s the case, expect a spiteful DM stating his identity.
“There is nothing worth getting steamed over or particularly excited about.” - Desson Thomson, Washington Post
The Quick and the Dead
This is about cowboys, and Leonardo DiCaprio plays one, in this movie, the one about cowboys, which he is in. So does Sharon Stone, and Gene Hackman, and Russell Crowe - in fact most of them do. A big bunch of gunslingers, the lot of them.
”Quick and the Dead plays like a crazed compilation of highlights from famous westerns. Raimi finds the right look but misses the heartbeat. You leave the film dazed instead of dazzled, as if an expert marksman had drawn his gun only to shoot himself in the foot.” - Peter Travers, Rolling Stone
The Great Gatsby
Leo is Gatsby, a very rich man who likes to throw big parties to impress his ex, and who isn’t impressed by big parties? I know I am! Take me now!
“More often, Gatsby feels like a well-rehearsed classic in which the actors say their lines ably, but with no discernible feeling behind them.” - Scott Foundas, Variety
Body of Lies
CIA big dog field-operative Leo on the hunt for an elusive terrorist this time, with ‘Russell Crowe in tow’, which is a nice rhyme, isn’t it? I like to have fun.
“A mostly formulaic approach that becomes more disappointing as the yarn unwinds.” - Todd McCarthy, Variety
Biography time, and in this case we’re not looking at the exciting life of the man who invented the vacuum cleaner, we’re actually all about the director of the FBI in the 1920s, in this case. All under the watchful eye of Clint Eastwood, and what a watchful eye it is.
“Most disappointing, Eastwood’s decades-spanning portrait reveals little about the man himself.” - Steven Rea, Philadelphia Inquirer
Romeo + Juliet
“Romeo, Romeo, Romeo, where are you then, oh Romeo? That is the question.” A modern retelling of Shakespeare’s famous play about star-crossed lovers, this is the second Baz Luhrmann film on the list, after The Great Gatsby.
“Mr. Luhrmann’s frenetic hodgepodge actually amounts to a witty and sometimes successful experiment, an attempt to reinvent “Romeo and Juliet” in the hyperkinetic vocabulary of post-modern kitsch. ” - Janet Maslin, The New York Times
This Boy’s Life
It’s time for some 1950s-set teenage rebellion now, with a smattering of evil stepfather thrown in. Also, if you’re in the market for a dumb new haircut, and need some inspiration. See above.
“Despite its admirable strengths and the fact of it being a true story, there is somehow a failure to completely connect with the fierce boy, giving his unhappy and alienating youth an unfortunate air of unreality.” - Angie Errigo, Empire
Hitchcock-esque Spooky time with Leo directed by Marty Scorsese in a strange psychiatric facility on a creepy island with twists and turns galore that you absolutely will positively not see coming. Probably.
“This quasi-horror film has the great director’s usual craftsmanship and a stellar cast, but ultimately it’s an infuriating trick that makes its most provocative ideas disappear.” Joe Williams, St. Louis Post-Dispatch
You know when you really just want to find this one particular diamond, but there are other people that want to find it, and you’ve got to race to beat them? Well, DiCaps does too, because that exact thing happens in this film. He also does a South African accent, which is incredibly distracting for at least the first 45 minutes.
“The combination of DiCaprio’s soulful, self-effacing work in Scorsese’s The Departed, and this unexpectedly complex portrait in a simple-minded movie, make it the best year of his career since the big boat crash of 1997.” - Liam Lacey, The Globe and Mail
Get your tissues out, everybody! Estranged sisters, ill fathers, bone-marrow transplants and a troubled son played by our boy - so obviously it won an Oscar. Have you ever heard of a more Oscar-worthy film? NOPE, NOPE YOU AIN’T.
“Tony Award-winning stage director Jerry Zaks’ debut feature is a gentle, surprisingly funny film about dying that manages to tug a few heartstrings without the usual emotional manhandling.” - TV Guide Magazine
Metascore: 69 (nice)
Fancy a lovely romantic drama about the perils of suburbia? Here’s one for you - set in the 1950s, it’s the Kate-Leo dream-team back again, doing what they do best: snogging. But this time around they have added another string to their bow: struggling to afford a house and be a married couple.
“Revolutionary Road isn’t a great movie – it lacks the full, soul-crushing force of the novel – but what works in it works so well, and is so tricky to pull off, that you can’t help but admire it.” - Scott Foundas, Village Voice
Gangs of New York
Gang bosses, big fights and revenge on the streets of 1863 New York, all because Daniel Day Lewis is shouting his mouth off again. Out of all DiCaprio’s films, I think this one is the one in which he sports the most terrible beard.
“Though never dull and often visually beautiful, this work of operatic sweep doesn’t fulfill its own ambitions.” - Jonathan Foreman, New York Post
What’s Eating Gilbert Grape
DiCaprio was only 18 when he starred in this drama, two years after Critters 3, which I have already mentioned is my favourite Leonardo DiCaprio film. I feel it necessary to remind you of this intermittently. Anyway, we’ve got an early Johnny Depp number here - lots of family drama, troubled relationships and the addition of a ‘free-spirit’ - bet she’ll shake things up!
“Leonardo DiCaprio, the vibrant young star of This Boy’s Life, gives an audacious and technically amazing performance as Arnie, the retarded 17-year-old whose soul, for all its anarchic buoyancy, remains trapped inside a compulsive network of grunts, guffaws, and grimaces. This is one nowhere boy who commands your attention.” - Owen Gleiberman, Entertainment Weekly
Jumping into other people’s dreams and stealing their secrets? Planting ideas in people’s minds? That’s Inception! All very serious though, this one - it’s Chris Nolan, remember? He made those really sincere movies about that bloke who dresses up as a giant bat.
“As engrossing and logic-resistant as the state of dreaming it seeks to replicate, Christopher Nolan’s audacious new creation demands further study to fully absorb the multiple, simultaneous stories Nolan finagles into one narrative experience.” - Lisa Schwarzbaum, Entertainment Weekly
Catch Me If You Can
The true story about the FBI’s hunt for master con-artist Frank Abagnale, Jr.. Can they catch the wily Leonardo, zipping around like a cat, putting on hats and doing accents? You’ll have to watch Catch Me If You Can to find out. If you’d rather not watch it for some reason or another, then I’d suggest Googling “Do they catch Leonardo DiCaprio in Catch Me If You Can?” - that will provide you with a similar answer, without nearly as much of the investment.
“What lingers in the memory is the impression of having experienced a frolic, a ride through the park on a bright winter day.” - Mick LaSalle, San Francisco Chronicle
The Wolf of Wall Street
This was not what I thought it was about. Disappointment doesn’t even begin to cover it. It’s actually about shifty traders, being illegal and doing drugs while making loads of money and standing on boats doing a ‘cheers’. It’s actually quite good to be fair.
“A delirious, manic, push-the-limits comedy of gaudy amorality that tests the audience’s taste. But it’s a gamble that works, since you leave this adrenaline trip wasted, but invigorated.” - Joe Neumaier, New York Daily News
Everyone’s favourite bit in this is when that man hits the propeller and can you please stop lying about it because it is.
“It’s a powerfully ersatz experience, but at least it’s powerful. There’s a lot to like here: At three hours and 14 minutes, the film takes longer to watch than the Titanic took to sink.” - Peter Rainer, Dallas Observer
This brilliant survival flick follows DiCaprio’s frontiersman as he survives in the wilderness after a harrowing near death experience. I give it nine bears-almost-killing-Leonardo-DiCaprio out of ten.
“While the style may outpace the substance, that doesn’t make the style any less magnificent. And when it comes to sheer customer satisfaction, The Revenant checks nearly every box, up to and including the man vs. wild throwdown. It just makes a jarring, memorable statement about how often the wild is likely to win that uneven fight.”
This biopic follows the life of director Howard Hughes, who harboured a number of debilitating conditions behind closed doors. Out of all of Leonardo DiCaprio’s films, the circumference of his head is smallest in this one.
“The Aviator has a hole in its center, and Scorsese fills it the only way he can, with spectacle. He makes The Aviator colorful and entertaining from beginning to end. There are worse things.” - Mick LaSalle, San Francisco Chronicle
This follows a freed slave who embarks on a revenge rampage, whilst wearing an impressive number of lairy suits. Also, shout out to Christoph Waltz for playing Christoph Waltz again. Leo plays a big ol’ racist.
“Django Unchained doesn’t merely hit its marks; it blows them to bloody chunks. It’s manna for mayhem mavens.” - David Edelstein, New York Magazine
So here it is, everybody - the best Leonardo DiCaprio film according to Metacritic. Scorsese’s remake of Hong Kong thriller Infernal Affairs, starring Leo, Jack Nicholson, Matt Damon, Martin Sheen, Ray Winstone and Vera Farmiga - a pretty fancy line up I think you’ll agree. Lots of double crossing, iffy accents, undercover police and shock deaths like SPOILER: that bloke who dies.
“A new American crime classic from the legendary Martin Scorsese, whose talent shines here on its highest beams.” - Peter Travers, Rolling Stone
So there you go - now you know which Leo film to watch next, providing you want to listen to real-life film critics and not some internet goblin that won’t stop banging on about Critters 3. Watch Critters 3, is what I’m trying to say, here.
The best Leonardo DiCaprio film, bar none.
“Really recommend watching this, and I’m not just including it to get a cheap laugh on an internet article” - Gary Ogden, Shortlist.com