The Tree of Life (2011)

An amazing film directed by Terence Malick. On one level it’s a story of an American family and how they deal with a bereavement. But the film is also designed as a work of art, constructed to operate on multiple levels of symbolism and philosophical exploration. 

Early on it detours into a history of life on Earth (perhaps influenced by 2001), showing dinosaurs and the meteorite that forced their extinction. It then returns to the story of the family. Brad Pitt and Jessica Chastain play the parents of three boys, while Sean Penn plays one of those boys as an adult in the present day and struggling to come to terms with his past. 

There are so many impressionistic elements that you’re often unsure what to think and what, if anything, is actually happening in narrative terms. That can be frustrating if you are expecting anything close to a regular drama. Indeed, the dinosaur segment borders on the ludicrous. 

If the job of the film is to take you on an emotional journey, then it’s too muddled to succeed. But if you embrace the sheer ambition of the project – in terms of its visuals, music, editing techniques and production – it’s unlike anything else you will see.

Carlito’s Way (1993)

Superb crime thriller.

Al Pacino plays Carlito Brigante, a Puerto Rican ex-con who is trying to make a fresh start. But his post-prison efforts to clean up are thwarted by a corrupt, drug-addicted lawyer friend (a suitably sleazy Sean Penn) and other remnants of his former criminal lifestyle. 

The story is told in flashback so we know what happens from the very beginning – which is a shame, in a way – but it’s fascinating to see how the plot winds back around to that point. 

Penelope Ann Miller is superb as Pacino’s love interest, who helps to redeem him. Brian DePalma’s direction is imaginative, utilising unusual angles and a fresh feel. Pacino as usual is hugely watchable – magnetic even – and oddly funny at the same time. It’s a masterful performance – one of his best.

21 Grams (2003)

Powerful and disturbing drama directed by Alejandro González Iñárritu and starring Sean Penn, Naomi Watts, Benicio Del Toro, Charlotte Gainsbourg and Danny Huston.

The plot interweaves the lives of several characters, told with extensive flashbacks. The mixed-up chronology can be challenging – it might have worked better in linear sequence – but the material is harrowing in any order. The relentlessly dark subject matter includes alcoholism, drug addiction, bereavement, born-again religion, relationship separation and terrible psychological anguish. 

Del Toro, Penn and Watts are all excellent, tackling extremely difficult scenes. It’s searing, gut-wrenching storytelling that is quite painful to watch. 

It’s visually striking, too. The colour and graininess of the film changes with the mood and tone of the events, but overall there’s very little lightness or hope offered.

Milk (2008)

Biopic of Harvey Milk, who campaigned for gay rights in California until his assassination in 1978. 

Sean Penn is superb in the main role, with a fascinating twitchy energy and a set of mannerisms that make him incredibly watchable. Josh Brolin is excellent as Dan White, a San Francisco city supervisor and political rival. 

The assassination is referenced right at the start, so you know what’s going to happen. As such it’s painful to watch the film proceed to its inevitable conclusion.

Gangster Squad (2013)

Gangster thriller set in Los Angeles in 1949.  

Sean Penn is Mickey Cohen, a brutal mobster. Sergeant John O'Mara (Josh Brolin) is a World War II veteran who leads a team of cops (including Ryan Gosling) to hunt him down. Emma Stone is Cohen’s girlfriend and “social etiquette teacher”, who becomes attached to Gosling, putting both of them in great danger. 

It’s exciting when there’s action taking place, and the chase and shoot-out sequences are exceedingly well filmed, but it's let down by a sub-standard script. The characters aren’t really developed, so you don’t see any of these excellent actors at their best. The group scenes are especially flat, with no one seeming to have anything to say. Even the Stone/Gosling pair-up – so potent in La La Land – fails to sparkle. 

There’s an interesting theme about the war not yet being over, and O’Mara not knowing what else to do but fight. Oddly enough, the most three-dimensional character is Connie (Mireille Enos), his pregnant wife, who goes from warning him about the dangers of what he’s doing to hand-picking the “gangster squad” who work with him.

Casualties of War (1989)

Directed by Brian De Palma, this tells the story of an American soldier in the Vietnam War (Michael J. Fox) who reports the other members of his squad for kidnapping, raping and murdering a Vietnamese woman. It’s loosely based on the 1966 “incident on Hill 192”, although names have been changed. 

Fox turns out to be fairly convincing as the squeaky-clean Lutheran who resists his sergeant (a believably on-the-edge Sean Penn). He just looks a little too fresh and healthy, even when he’s sent to hospital, and his hair never seems to get ruffled. In contrast, the war scenes are scary and realistic. 

The music is by Ennio Morricone and – despite its appeal – seems a little too prominent for certain scenes.

The Assassination of Richard Nixon (2004)

Based on a true story, this is a gripping and desperately sad drama starring Sean Penn. He plays Samuel Bicke, a furniture salesman who is suffering at work and in his personal life and who – amid a mental breakdown – decides to kill the president. 

Penn is absolutely superb, making you feel his utter isolation and his heartbreaking descent through a series of personal tragedies. He is estranged from his wife (Naomi Watts) and children, is bullied by professional colleagues and sees his plans to set up his own business rejected. 

Nixon himself is cleverly woven into the story through the use of archive footage shown on news broadcasts. 

When Bicke finally undertakes his assassination attempt we really feel for him. It’s not that you’re rooting for him to succeed – history already tells us that he will fail – but you yearn for him to be happier and to find peace.

The Interpreter (2005)

An interpreter at the United Nations (Nicole Kidman) overhears a conversation that suggests the leader of an African state is to be assassinated when he arrives to make a speech. A recently widowed Secret Service agent (Sean Penn) investigates and senses that she’s not telling the full truth, but the pair are drawn together by their shared losses. 

Directed by Sydney Pollack, it’s a smart and sensitive thriller that’s very nicely shot. Kidman and Penn are both excellently drawn characters and their relationship is subtle and nuanced. Catherine Keener is great as Penn’s professional partner, but doesn’t get given enough lines. 

The plot is complicated and there might be a few loose ends. For example, the phrase that the interpreter overhears doesn’t make sense in the light of what ultimately takes place. But that doesn't spoil an excellent thriller.

Mystic River (2003)

Compelling drama directed by Clint Eastwood. 

Three Boston-based childhood friends are reunited in unhappy circumstances. They discover how the events of their youth have shaped their lives and relationships, and continue to do so as events play out in the present day. 

Sean Penn is the gangster-like Jimmy Markum. Tim Robbins is Dave Boyle, who has become a damaged, haunted man after being abused as a child and now finds himself the prime suspect in the killing of Jimmy’s daughter. Meanwhile, Kevin Bacon is a detective named Sean Devine (assisted by a further detective played by Laurence Fishburne). 

The performances are hugely credible, leading to an unbearably tense couple of hours as this painful human tragedy plays out.

Fair Game (2010)

Superb thriller. Adapted from the memoirs of the two protagonists, it tells the story of CIA operative Valerie Plane and her diplomat husband Joseph C. Wilson. The pair were responsible for exposing the US government’s fabrication of the evidence about Weapons of Mass Destruction that was used to justify the invasion of Iraq. 

Naomi Watts and Sean Penn deliver remarkably convincing performances in the lead roles. There’s the political saga, but also the story of their marriage and family, and the strain that these events put on them. 

I admire the realism of it, such as the way that every scene featuring the couple’s children had them constantly asking questions and demanding attention. I also respect the film for delving into the moral ambiguities of the topic – should you tell the truth even if it puts loved ones at risk? – and not providing any simplistic answers.

The Secret Life of Walter Mitty (2013)

Walter Mitty (Ben Stiller) works at Life magazine as a “negative assets manager”. His world is humdrum but he daydreams incredible and heroic scenarios, often involving a colleague he has a crush on. When the magazine is threatened with closure and their jobs are endangered, Walter needs to locate a missing photographic negative for the image that will feature on the magazine’s final front cover. This takes him on a journey to Greenland, Iceland and Afghanistan in search of a photojournalist (Sean Penn), as his actual existence becomes as remarkable as his fantasy life. 

Stiller is charming as the “dull” worker who inevitably becomes a rugged hero. Kristen Wiig is hugely appealing as the woman he falls for (and she even gets to sing him David Bowie’s “Space Oddity”). Shirley MacLaine is a nicely rounded character as his mother. 

This rousing film is funny in places (such as Stiller’s ongoing conversation with a dating agency) and heartwarming in others (you root for him to keep his job and win over the girl). Often it looks like a mobile-phone advert (vivid colours, exotic locations, emotive music), but oddly that works because the idealised escapism of unreality is a central theme. 

It’s unusual, rewarding and refreshing.

Thin Red Line (1998)

Ensemble film about WWII adapted from the 1962 James Jones novel. It presents multiple narrative perspectives. Unlike The Longest Day, it actually works. The all-star cast includes John Cusack, George Clooney, Nick Nolte, Sean Penn, John Travolta and Woody Harrelson, although Clooney and Travolta are barely there beyond brief cameos. Jim Caviezel and Ben Chaplin are especially strong.

It can be confusing at times, as the interior monologue switches between characters depending on who’s being shown on screen. Plus, the signposting of the wheres and whens of certain scenes can seem muddled.

It’s epic and expansive, also demonstrating a strong love of nature: there are long, lingering shots of wildlife and the long grass blowing in the wind. The action sequences are harrowing. And it builds up a philosophical depth as it goes along.