Once Upon a Time in Hollywood (2019)

Fascinating comedy-drama written and directed by Quentin Tarantino. 

It’s 1969 in Los Angeles. Rick Dalton (Leonardo DiCaprio) is an actor famous for his role in a 1950s TV western. His best friend is his stunt double and personal assistant Cliff Booth (Brad Pitt). Times are changing and the pair are struggling to stay relevant in the film industry. Their next-door neighbours are actress Sharon Tate (Margot Robbie) and her director husband Roman Polanski. Also on the fringes of the scene is a young Charles Manson…

The film cleverly weaves together fact and fiction across multiple narratives, playing on what we know – or think we know – about the mythology of the Manson murders. It’s a kind of alternative history that finds humour and tragedy in the events, but not in the way that you might expect.

It’s visually rich and full of the iconography of the time, with Tarantino really relishing the period detail. Highly watchable stuff.

Gangs of New York (2002)

One of Martin Scorsese's lesser works. As a fan, I found this a big disappointment.

Fragmented and unfocused, it tells the story of the feuding Catholic and Protestant groups in the New York of the 1860s. At the same time, Amsterdam Vallon (Leonardo DiCaprio) seeks revenge from William "Bill the Butcher" Cutting (Daniel Day-Lewis), who killed his priest father (Liam Neeson).

Scorsese tries to tell too many stories and loses track of the multiple threads.

There's slightly naff Irish music running through the film, which drags on for 167 minutes.

DiCaprio doesn't get to act much, which is a missed opportunity, and Cameron Diaz (who plays his pickpocket girlfriend) doesn't bring a great deal to the role.

There was possibly a great film in here somewhere, but possibly it got lost in the edit.

The Wolf of Wall Street (2013)

The curiously featureless face of Leonardo Di Caprio works perfectly to represent the banality of ultra-greed in Martin Scorsese’s audacious biopic of non-legal trader Jordan Belfort. 

The aesthetic is bland and corporate, as it should be. Scorsese avoids the subtle layering of American Hustle and instead opts for relentlessness, brilliantly pushing the excess factor. Some of the speeches by the “wolf” are incredibly well done – a much more extreme twist on the “greed is good” theme of Michael Douglas as Gordon Gecko in Wall Street. 

Some critics complained that there’s no moral core, but surely that’s the point of this film. The book is even better. Jordan’s written account condenses certain episodes in his life. The film further combines and condenses, so inevitably drifts towards fiction.

A diverse cast also includes Jonah Hill, Margot Robbie, Rob Reiner, Joanna Lumley and Matthew McConaughey.

Marvin's Room (1996)

Touching family drama. 

Two estranged sisters (Diane Keaton and Meryl Streep) get to know each other in the context of an elderly, unwell father and a troubled teenage son (Leonardo di Caprio). 

It’s based on a play by Scott McPherson, and you can tell because the writing is so strong. Each of the characters is extremely well drawn and the relationships between them are explored with depth and empathy. Keaton is particularly strong as a woman with leukemia.

J. Edgar (2011)

Directed by Clint Eastwood, this is a surprisingly dull biopic given the rich source material. 

J. Edgar Hoover (Leonardo DiCaprio) looks back on his life and work as the head of the FBI. Along the way we learn about his repressed homosexuality and a series of world events as presidents come and go. 

Naomi Watts is wasted as a secretary with little to go on in terms of a fleshed-out character. Judi Dench is much better as Edgar’s domineering mother. Much of the story is told in flashback and the worst aspect is the prosthetics used to age the character. DiCaprio and Watts look OK, but Armie Hammer as Clyde Tolson looks comically awful in his rubbery “older” face, and it’s a major distraction. 

In a very brief appearance only, Adam Driver makes his film debut.

Blood Diamond (2006)

An engrossing drama directed by Edward Zwick. 

A diamond smuggler working in Sierra Leone (Leonardo DiCaprio) begins to examine his motives after meeting an American investigative journalist and a local man who has been separated from his wife and son. 

DiCaprio is compelling but not quite at his best. Maybe it’s his South African accent that makes him a little less convincing than usual. That said, his character development as the film progresses is extremely well done. I liked Jennifer Connelly as the journalist, too. 

The film makes some strong moral points about trading in "conflict diamonds", but because DiCaprio’s character is presented as amoral it’s not as heavy-handed or judgemental as it might have been.

Shutter Island (2010)

US marshal Teddy Daniels (Leonardo DiCaprio) is sent to a Boston Harbour island. With his companion (Mark Ruffalo), he is looking into the disappearance of a patient from the Ashecliffe Hospital for the criminally insane. But he’s quickly swept into a deeper mystery about what’s really going on at the asylum. 

Directed by Martin Scorsese, this is a genuinely terrifying psychological thriller. Leonardo DiCaprio is superb as a complicated character making a horrible discovery. 

It’s closer in tone to Cape Fear than anything else I’ve seen by Scorsese. What seems to be a noirish thriller acquires extra depths as it becomes stranger and even more disturbing. It’s difficult to say any more without giving away the big twist. 

The superb cast also includes Ben Kingsley, Michelle Williams and Max von Sydow.

The Beach (2000)

An adaptation of the popular novel by Alex Garland. 

A young American traveller called Richard (Leonardo DiCaprio) goes in search of a mythical island – and finds it. There, he joins an idealistic community led by Sal (a believable Tilda Swinton). But he soon discovers that this is far from the paradise he dreamed of.

DiCaprio is superb in the main role. His mixture of arrogance and vulnerability seems very real. 

I’m less keen on some of the stylings from director Danny Boyle, such as when Richard imagines he’s within a video game and the film becomes one. But the story and acting are so strong that you are swept along by the plot anyway.

The Departed (2006)

Directed by Martin Scorsese, this remarkable crime thriller is as good as any. 

In Boston. Irish Mob boss Frank Costello (Jack Nicholson) places Colin Sullivan (Matt Damon) as a spy within the police force. Sullivan quickly rises up the ranks, becoming a highly respected detective, and protects Costello by feeding him information. Meanwhile, the police assign undercover agent Billy Costigan (Leonardo DiCaprio) to infiltrate Costello’s criminal gang. And both of them end up dating the same police psychologist (Vera Farmiga as Dr. Madolyn Madden). 

It’s incredibly clever. The plot moves fast enough to make your head spin, but Scorsese’s storytelling gifts are such that it works. 

The all-star cast also includes Alec Baldwin, Martin Sheen, Ray Winstone and Mark Wahlberg. The soundtrack is terrific, although a repeat use of the intro to “Gimme Shelter” by the Rolling Stones in the same scene seems like an error. 

As usual with Scorsese, you get everything – a masterclass in film-making. The characters are richly fleshed out. It’s thrilling. It looks visually stunning. And the script is really sharp.

The Aviator (2004)

Biopic of billionaire entrepreneur Howard Hughes, directed by Martin Scorsese and starring Leonardo DiCaprio. 

It’s a sad and engrossing story that expertly details Hughes’ decline into paranoia, social reclusiveness and the crippling discomfort of extreme OCD. 

Scorsese’s usual tricks are all displayed, but it’s refreshing to see them used in a non-crime story. At times it all seems a little too stylised, but then Scorsese handles this visual flamboyance so well that he makes it work. Plus, it’s a film about the veneer of Hollywood success so that lavish styling serves to further underscore the subject matter. 

DiCaprio is absolutely superb as the visibly crumbling Hughes. Cate Blanchett is also at her best, capturing the quick-witted energy of Katharine Hepburn. 

Also popping up are Kate Beckinsale (as Ava Gardner), Ian Holm, John C. Reilly, Alec Baldwin, Jude Law, Gwen Stefani (as Jean Harlow), Willem Dafoe and Alan Alda (as Senator Ralph Owen Brewster).

Body of Lies (2008)

Intelligent Ridley Scott CIA thriller that’s extremely gripping. 

The CIA operative on the ground is Leonardo DiCaprio and his superior is Russell Crowe. They are attempting to track down a terrorist called al-Saleem. 

Mark Strong plays the head of Jordanian Intelligence. Oscar Isaac is a CIA field operative in Iraq. And Rahavard Farahani plays a nurse who DiCaprio falls for and thus endangers. 

All of these actors are superb in their roles. 

It’s a complex web of connections and locations. It’s extremely violent for a “15”, with scenes of torture and close-ups of shootings. The use of drone-sourced visuals gives it an appealing tech-heavy feel.

Romeo + Juliet (1996)

Modernisation of the Shakespeare play starring Leonardo DiCaprio and Claire Danes in the main roles. They are both excellent and their love scenes zing with energy and sensual yearning. But the film is directed in such a self-conscious manner as to be almost unwatchable. I really disliked the speeded-up sequences, and the awfully clunky opening moments in a gas station had me about to turn off the film and hurl the DVD across the room. It may have been deliberate to make the other characters grotesque and cartoonish, but it just doesn’t work. Are we meant to find them comical or endearing? In fact, the effect is oddly repulsive.

A less tricksy approach might have developed (rather than risked sabotaging) the romance narrative and allowed the DiCaprio/Danes chemistry to dominate. It’s one of the all-time great stories – source material this strong really shouldn’t be difficult to film – but Baz Luhrmann somehow manages to mess it up.

The highlight is the Radiohead song over the closing credits.

The Revenant (2015)

Unrelentingly grim and bloody tale of North American frontiersman Hugh Glass (Leonardo DiCaprio) trying to survive against all the odds. It’s 1823, and desperate, isolated communities of trappers and hunters battle it out in the frozen wilds. Everything horrible you can imagine happening to Glass happens to him. He witnesses his wife’s murder. He’s attacked and badly maimed by a bear. He’s nearly smothered to death by a crazed colleague. He’s buried alive. He witnesses his son’s murder. He’s swept away in river rapids. He’s shot at. He falls off a cliff into a tree. And he has to sleep inside his dead horse (after pulling out the innards). Plus, he’s intent on exacting his revenge – whatever the cost.

It’s not exactly cheerful. But the film has a primal intensity that keeps you hooked. The scenery is stunning. And DiCaprio is watchable, even beneath the beard, blood, filth and fur. Ultimately, though, it’s too harrowing and brutal to constitute entertainment. It’s unclear what you’re meant to take away from it. I was left feeling troubled and disturbed.

Revolutionary Road (2008)

This faithful adaptation of the 1961 novel by Richard Yates is a fairly bleak study of oppressive suburban conformity in 1950s America, and the perils of trying to dream your way outside of it. The Wheelers are played by Leonardo DiCaprio and Kate Winslet, who famously played the couple in Titanic. (Kathy Bates is also in both films.) In fact, it almost works as Titanic II, extrapolating how their lives might have evolved had Jack lived, married Rose and settled down to have a family. Suburban malaise is expertly depicted, with a sense of desperation and emptiness always at the edges of their wealthy, comfortable existence. From the outside, they are “special” – the “perfect couple” – but the rigid gender roles and social expectations of their time and place form an invisible prison they both rage against in different ways. Ultimately the unrelenting hopelessness of it all does become a bit overwhelming, even though that hopelessness is extremely well imagined.

Inception (2010)

Barnardo’s, Whetstone. Baffling Christopher Nolan thriller about espionage conducted within dreams – on multiple levels. Buried within a highly convoluted plot is a powerful film about loss and grief, but it fails on many levels. There’s no chemistry between the characters, despite the excellent Leonardo DiCaprio. Parts of the multi-level-dream plot don’t really make sense. Plus, the trial-run worlds created by the female dream architect were far more interesting than the actual ones in which the bulk of the film is set. So instead of her streets that bend and warp psychedelically (as "borrowed" for Doctor Strange), you get a hotel plunged into zero gravity (mildly diverting) and a bog-standard building in a snowscape (Bond film meets Hoth’s Echo Base in The Empire Strikes Back). I still don’t understand why the team were being constantly shot at, and the effect of all this is ultimately numbing. With hard-to-love characters and worlds within worlds that aren’t real, why should you care about any of it?

Titanic (1997)

I enjoyed this far more than I expected to. I have always found disaster stories fascinating, and this one is especially well done. The slow build is effective, setting up the theme of class inequality that is just as relevant now as it was in 1912. The scenes of the ship filling up with water are heartbreaking. James Cameron truly understands how to convey scale and spectacle.

I could have done without the “old lady looking back” aspect, which adds little and could have been cut entirely, but I suppose they wanted to make it a century-spanning epic.

Kate Winslet and Leonardo diCaprio are fantastic as the doomed young lovers.