10 films every gentleman should see at least once

We look to movies past and modern to compile the ultimate top ten

Who doesn’t love a good film? Something to take our minds off the day-to-day, transporting us to another world for a couple of hours and getting our minds racing and hearts thumping. Of course, some are better than others and, every once in a while, a truly great film comes along, and imprints itself so irreversibly on our minds and culture that we keep talking about it for years.

This list contains just those films. Obviously, there are great ones left out – 10 is but a drop in the ocean of cinematic greatness – but these are the best films you should watch at least once in your lifetime if you consider yourself, or aspire to be, a gentleman.

Rebel Without a Cause, 1955

Starring a brooding James Dean as a young troublemaker looking to make a name for himself, Rebel Without a Cause defined a generation with its story of rebellion, restlessness and misunderstood youth. 

Why should you watch it?

A tale about youthful defiance set in conformist mid-1950s America could easily have been exploitative, but Rebel Without a Cause never goes in that direction. Instead, we get a nuanced and stylised view into that world through the lens of a riveting male character, played to perfection by a true icon.

The Italian Job,1969

Another all-time classic, this deliciously British comic caper is a heist story that’s not really about the money or the loot, but focuses instead on betrayal and revenge among a motley crew of thieves.

Why should you watch it?

The Italian Job is worth your time for the climactic car chase sequence alone. And of course, there’s the stellar cast of top-of-their-game actors, led by the indomitable Michael Caine in his unflinching embodiment of Sixties cool.

Apocalypse Now, 1979

Raw, gritty and thoroughly nihilistic, Apocalypse Now is considered by many to be the greatest war movie ever made.

Why should you watch it?

This Vietnam War epic is one of Francis Ford Coppola’s finest (and weirdest) films, with Marlon Brando and Martin Sheen both putting in totally madcap – and utterly compelling – performances that deserve to be seen by every gentleman.

Wall Street, 1987

Director Oliver Stone’s depiction of 1980s corporate greed is one of the most celebrated and referenced pieces of financial cinema ever made.

Why should you watch it?

If you’re a trader, a banker or any kind of moneyman, you absolutely have to watch this film because it will, in some way, be relevant to you. For everyone else, Michael Douglas’ star turn as legendary corporate raider Gordon Gekko is itself worth the two hours and six minutes of your time. 

Groundhog Day, 1993

Directed by the late Harold Ramis and starring fellow-Ghostbuster Bill Murray, this fantastic story about a cocky weatherman living out the same day over and over thoughtfully touches on themes of time, life and, yes, love. 

Why should you watch it?

If it was good enough for Bill Murray to be in, then it’s good enough for all gentlemen to see. He really is that good.

The Shawshank Redemption, 1994

Way more than just a prison-break story, The Shawshank Redemption is arguably the best film ever made that looks into one of the most human of all drives: to never give up.

Why should you watch it?

Brilliantly shot, with a brilliant script and brilliant acting, the movie will entertain you and shock you at every turn. The ending is also one of the greatest fist-bump moments in cinematic history.

American Beauty, 1999

This at-once cynical, dark and uplifting story of suburban Americana is a true high point of late 90s Hollywood filmmaking.

Why should you watch it?

For any gentleman going through a midlife crisis, American Beauty should sort you out. Starring Kevin Spacey as Lester Burnham, a man whose boring straight-edge life leads him to become more and more unhinged, it acts as a showcase of what every gentleman should actively try to avoid.

Gladiator, 2000

Russell Crowe has starred in his fair share of epic films throughout his career, but if you’re going to watch just one, it has to be Gladiator.

Why should you watch it?

With its amazing fight scenes, costumes and world-building, Gladiator singlehandedly made the Roman Empire cool again. Inspiring, emotional and perfectly executed, the film really does have it all.

Rush, 2013

Rush is an exhilarating ride from start to finishing line, telling the story of one of Formula One’s most exciting rivalries, that of Niki Lauda and James Hunt in the 70s.

Why should you watch it?

At its core, Rush is a hauntingly moving tale of conflict and friendship between two very different – and very real – gentlemen, making it a must-watch for anyone.

Birdman, 2014

A dark comedy that wears its lack of self-seriousness like a badge of pride, Birdman tells the story of a former movie superhero who mounts an ambitious theatre production to revive his near-dead career.

Why should you watch it?

For Michael Keaton, plain and simple. Perfectly cast (remember he was Batman once upon a time), he delivers a truly stand-out performance that’s layered with poignancy and panache in equal measure.   

Dunkirk, 2017

Christopher Nolan’s epic combat thriller about Allied retreat at the start of the Second World War is both nerve-wracking and emotionally satisfying. One of the best films to come out in recent times, hands down.

Why should you watch it?

Films don’t get more immersive than this. Thanks to Nolan’s absolute mastery of the camera, you’ll be plunged straight into the action and come out of it feeling like you were actually there. An amazing movie, about men doing both terrible and amazing things.   

Further Reading