Seven Christmas Films for the Discerning Gentleman

Seven Christmas Films for the Discerning Gentleman

By Chris Cotonou

As we approach the depths of the holiday season, you’re probably starting to get into the habit of sitting back, taking some time off, and enjoying a few warm evenings indoors. There’s some obvious ways to pass the time. Since you’re here with us, it’s very likely you’ll be opening your humidor and grabbing a good Cuban cigar. Then, soon after, you might pour a glass of something strong and get into the groove of the festive season. But what better way to accompany these delights than switching on a merry Christmas movie? We’re not speaking about the gratingly cheesy cookie-cutter stuff that gets churned out every year, but thoughtful, heartwarming flicks – longtime favourites – that are sure to get you into the festive spirit.

Here are seven of our picks to stream now. The perfect accompaniment to those winter nights of deep, cosy hibernation.

The Apartment (1960)

The Apartment

The Apartment, 1960

Bud Baxter (Jack Lemmon) has a problem. His boss wants to host his secret affairs and parties at his apartment, and if Baxter disagrees with letting him use the place, it could cost him his job. This is the brilliant premise of Billy Wilder’s Christmas favourite, set against the bright lights and tenement buildings of New York City in the holidays. The romance that unfolds is made more spectacular as the spirit of goodwill, with a Mad Men office backdrop of tungsten lights that contrast with the festive decorations. The Apartment is a classic, and sure to put a smile on your face.

Metropolitan (1990)



Metropolitan, 1990. Credit: Criterion

A simple, witty tale about a regular young man trying to fit in with New York City’s social elite. Tom Townsend makes his move in the holidays – as posh teenagers visit private dinner parties, shop their silk foulards and tuxedos from Brooks Brothers, smoke, drink, and debate their vacuous philosophies. It offers a glimpse into an era that we often look back on with some nostalgia today, and as preppy fashions (and attitudes) resurface again, Metropolitan seems as relevant as ever.

It’s a Wonderful Life (1946)

It's a Wonderful Life

It's a Wonderful Life, 1946. Credit: AP Photo

The definitive Christmas film. You’ve probably already seen It’s a Wonderful Life countless times. But just in case you missed it, this is the story of George Bailey, who gives up on his dreams and plans to end his life on Christmas. At least, until divine intervention plays its part. Featuring a never-more-charming James Stewart, this is an uplifting ode to life, and a reminder to appreciate what we already have. Just as Clarence says: “No man is a failure who has friends.”

The Santa Clause (1994)

The Santa Clause

The Santa Clause, 1994. Credit: Amazon

While so many iconic Christmas films are from over half-a-century ago, there are still a recent few that serve up festive nostalgia. The Santa Clause, starring Tim Allen as ‘Scott Calvin’ (see where we’re going?), is one of them. It’s the story of a man who ‘kills’ Santa, and thus, must take over the job. Somewhat of an adult’s Christmas movie, it depicts humorous segments on North Pole legal issues, an elf Special Forces, and more. At its core, this is a heartwarming Santa story about a father and son. It also includes a pair of the smoothest silk pyjamas in celluloid history. Really.

Kiss Kiss Bang Bang (2005)

Kiss Kiss Bang Bang

Kiss Kiss Bang Bang, 2005. Credit: Amazon

As with the Die Hard debate, is it truly a Christmas film simply because it’s set during the holiday season? We say, yes. Die Hard, much like Kiss Kiss Bang Bang, is made more memorable because of the Christmas setting, providing a strange contrast to the violent murder-mystery. Filmed in Los Angeles, and featuring great turns by Robert Downey Jr and Val Kilmer, the Raymond Chandler-esque vibe and dark humour has become a cult favourite. One we think you’ll appreciate if you’re in the mood for something other than the usual sentimental family fables.

A Christmas Tale (2008)

A Christmas Tale


A Christmas Tale, 2008. Credit: Criterion

We’re going to France now, and spending time with one very, very dysfunctional family. The Vuillards are typical ‘bourgeois-bohemes’ who gather around Christmas to unpack some of their festering drama. One of acclaimed director Arnaud Desplechin’s most beloved films, there’s enough humour here to stop it from being overly-tragic. The season is all about family, and A Christmas Tale delivers a look into one that may, or may not be, rather familiar.

The Holiday (2006)

The Holiday

The Holiday, 2006. Credit: Amazon

Here’s one for the romantics (or perhaps when your other-half is joining you.) The Holiday is a crowd-pleasing rom-com set between Los Angeles and England, featuring Kate Winslet, Cameron Diaz, and Jude Law. Sure, it’s not the deepest film on the list, but it comes with plenty of heart – as well as a charming turn by the legendary Eli Wallach. And with so many of us wanting to be whisked away on holiday, the film offers just enough escapism so that the cross-cultural cheesiness is bearable. At the very least, she’ll be happy you chose it.

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