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2025 Heistmas Advent Calendar Day 18: ‘The Man Who Came To Dinner’

Brutal insult comedy meets Christmas hijinks in this brilliant 1941 film that absolutely slays today!

Monty Woolley
Photo: Tubi

Welcome to the 2025 Heistmas Advent Calendar, a daily drop of pop culture Christmas icons, oddities, and joy. Check back every day from now through December 25 for each daily entry!

Why isn't 1941's The Man Who Came To Dinner known the world over as a Christmas classic? IT IS!

The poster for The Man Who Came To Dinner, with a cartoon of a bearded man sneering at photos of two women and a large-nosed man.
The Man Who Came To DinnerPhoto: IMDB

This film came out of nowhere this December to rocket to the top of my list of must-watch Christmas films. It's SO GOOD. And, more importantly, it's SO FUNNY. I know Gen-Z kids don't care much about black and white films, but I have to say that the only reason this came on my radar was because of a Tik-Tok edit of the best lines. I'd heard of it by name for decades, but never had the chance to experience it. And believe me, you experience this film.

It's based on a play by George S. Kaufman, the hand behind some of the best Marx Brothers films, and Moss Hart, the hand behind A Star Is Born. The stage pedigree shows because most of it, like a play, takes place in a single location: a rich family's living room. Radio humorist Sheridan Whiteside, played by Monty Woolley who originated the role on Broadway, is doing a lecture tour through the Midwest, despite writing off all the people living there as idiots. He's reluctantly agreed to have dinner at the stately home of small-town Illinois notables Ernest and Daisy Stanley (Mr. Smith Goes To Washington's Grant Mitchell and The Wizard of Oz's Billie Burke), but when he slips on their icy stairs and breaks his hip, he's confined to a wheelchair and can't leave their house.

And people, Sheridan Whiteside makes their lives hell by being a cunty, cunty bitch. On one hand, he keeps getting more and more elaborate "get well soon" gifts sent to their house, including an octopus, penguins, and a sarcophagus. On the other, he just wants to be a cunty bitch to the Stanleys, because how dare he be trapped in their house! He insults them and their staff constantly (and creatively), convinces their daughter to elope with the labor agitator who's organizing a union at Mr. Stanley's factory, invites a gang of felons for a meal because they've formed a Sheridan Whiteside fanclub in prison, has his wisecracking showbiz friends (including Jimmy Durante as the lecherous comic "Banjo") visit to cause havoc, and insists on recording his Christmas Eve radio show from the Stanley's house, including a performance from a full children's choir.

Lobby card for the Man Who Came to Dinner, showing a man with a beard in a wheelchair and two well dressed women by a Christmas tree.
Monty Woolley's name should be first, he seriously runs away with this role.Photo: Warner Brothers

There's also a subplot where his long-suffering assistant, played by Bette Davis, falls in love with a local newspaperman, and Whiteside works behind the scenes to sabotage this relationship. After all, she's the only one who'll put up with his shenanigans.

Much like Kaufman and Hart's other comedic play-turned-film, You Can't Take It With You, everything is chaotic for 4/5th of the runtime, but turns out for the best in the end. The real star here is Monty Woolley, the fast-talking intellectual who hobnobs with royalty one minute and is absolutely devastating the Stanleys and their house staff (including Mary Wickes who played the nosy innkeeper in White Christmas) the next. It's Woolley's performance that elevates this film into the superstardom of Christmas comedies. Take a look at some of his best moments:

The whole debacle takes place before and on Christmas day, adding both a festive, wintry overlay and an added element of lunacy to the film. For all that it's about the characters screwing up each others' lives, it's also a Christmas movie because … uh … because it happens at Christmas. I'm going to level with you, no one learns any Christmas lessons or becomes a better person because of Christmas itself, but the whole thing has a background of ice skating, Christmas trees, presents, and snow. It's a Christmas movie as much as Die Hard is a Christmas movie, which it is.

The Man Who Came To Dinner is streaming on Tubi and is well worth the watch. It's the 1940's epitome of "oh damn, he went there" and a beautifully written insult comedy to boot. Well worth adding to the pantheon of Christmas comedies with Elf and Christmas Vacation!

Check back tomorrow for even more Heistmas Advent Calendar Goodies!

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