The 20 films every gentleman should watch in his lifetime

There are certain films every gentleman should watch. Here's the definitive list.

There are a handful of films out there that have a place in history as defining moments of popular culture; true icons of style, story and substance. The right kind of films have the capability to completely transport a person into a different moment of time. Some of the greatest stories of all time have been told through the beautiful medium of film – but which are the ones that made the cut? Look no further, gentlemen, for 20 films that you absolutely must watch.

The Talented Mr Ripley, 1999

The 20 films every gentleman should watch in his lifetime

Anthony Minghella’s thriller is worth watching for the wardrobe alone. It’s one of the most stylish films of all time, and provides a stella lesson in off-duty summer dressing.

Fight Club, 1999

The 20 films every gentleman should watch in his lifetime

Brad Pitt shines in this dark, twisted tale of an underground street fighting club.

Annie Hall, 1977

The 20 films every gentleman should watch in his lifetime

Although the vast majority of Woody Allen’s filmography is worth watching, Annie Hall is arguably his finest work. It charts his up-and-down relationship with Hall (Diane Keaton), and features plenty of out-of-this-world imagery.

Taxi Driver, 1976

The 20 films every gentleman should watch in his lifetime

One of De Niro’s most striking performances ever, Taxi Driver is a haunting take on the decay of urban city life.

Apocalypse Now, 1979

The 20 films every gentleman should watch in his lifetime

The Vietnam War epic is one of Francis Ford Coppola’s finest. Marlon Brando and Martin Sheen put in some truly great performances, too.

Gladiator, 2000

The 20 films every gentleman should watch in his lifetime

Russell Crowe has starred in his fair share of epic films throughout his career. If you’re going to watch one though, Gladiator has to be it. Inspiring, emotional and perfectly executed, it really does have it all.

American Beauty, 1999

The 20 films every gentleman should watch in his lifetime

For those gents suffering the dreaded mid-life crisis, American Beauty should sort you out. Kevin Spacey delivers his trademark dry wit through the character Lester Burnham, who is fed up of his mundane suburban life.

The Italian Job, 1969

The 20 films every gentleman should watch in his lifetime

Few car chase sequences are as memorable as the one in The Italian Job. The film is a classic and well worthy of a spot on this list.

Rebel Without a Cause, 1955

The 20 films every gentleman should watch in his lifetime

The brooding James Dean defined a generation in Rebel Without a Cause, starring as a young troublemaker looking to make a name for himself.

Pulp Fiction, 1994

The 20 films every gentleman should watch in his lifetime

Pulp Fiction is Tarantino’s best ever film, having received lashings of critical and commercial success over the years. Its inter-twining stories, pin-sharp script and unforgettable characters ensure it won’t be forgotten any time soon.

Shawshank Redemption, 1994

The 20 films every gentleman should watch in his lifetime

If there’s one thing to learn from Shawshank Redemption, it’s to never give up. Andy Dufresne is wrongly convicted of murder, yet he accepts his fate, forging a legendary status in the process.

The Godfather, 1972

The 20 films every gentleman should watch in his lifetime

The Godfather is often heralded as the greatest American movie of all time – it’s practically faultless. Ensure you watch the second one shortly after.

The Godfather II, 1974

The 20 films every gentleman should watch in his lifetime

Often hailed as even greater than its predecessor, The Godfather II follows the early life and career of Vito Corleone in 1920s New York while his son expands himself at the helm of the crime scene throughout America.

To Catch a Thief, 1955

The 20 films every gentleman should watch in his lifetime

The Alfred Hitchcock-directed To Catch a Thief stars Cary Grant and Grace Kelly, and is set in the French Riviera. What’s not to love?

Dr No., 1962

The 20 films every gentleman should watch in his lifetime

This is the film that kicked off the most successful movie franchise of all time. It’s far more stripped back than later Bond’s, yet it features everything you could want from a 007 movie; multiple beautiful women, stunning locations and of course, Sean Connery.

The Thomas Crown Affair, 1968

The 20 films every gentleman should watch in his lifetime

The ultimate heist film. Steve McQueen is a calculatingly suave millionaire, who believes he’s pulled off the perfect robbery. He also demonstrates how to dress (and smoke) like a gentleman.

Goodfellas, 1990

The 20 films every gentleman should watch in his lifetime

Following the life story of Henry Hill, Goodfellas is a masterpiece of cinema. Martin Scorsese based the film on Nicholas Pileggi’s novel “Wiseguy”, and it perfectly encapsulates everything we love about the gangster genre.

Cool Hand Luke, 1967

The 20 films every gentleman should watch in his lifetime

Any film with Paul Newman is guaranteed to be a sartorial hit, and if you’re looking to learn everything there is about being a gentleman, look no further than Cool Hand Luke.

Deer Hunter, 1978

The 20 films every gentleman should watch in his lifetime

No list such as this is complete without an epic war movie, and Deer Hunter is the perfect starting point. Perhaps one of Di Niro’s finest pieces of work, Deer Hunter follows a trio whose lives change forever after they fight in the Vietnam war.

Rush, 2013

The 20 films every gentleman should watch in his lifetime

From start to finish, Rush is an exhilarating ride. It looks at one of Formula One’s most exiting rivalries, that of Niki Lauda and James Hunt, as they battle throughout the 70s.

Further Reading