Deciding what to watch with your family over the holidays is akin to playing Mario Kart. You can be in first place, cruising along when BAM! One of those pesky red shells hit you and now you’re in last place. One minute, you’re sitting down for dinner and everything’s running smoothly, then someone turns on the TV and it offends Uncle Fred, and before you know it everyone is screaming and someone brings up something you did ten years ago.
To avoid these snafus, we’ve created this handy list of what to watch for every generation.
The Silent Generation
Born and raised in the shadow of the Great Depression and World War II, the Silent Generation, now in their late 70s, 80s, and 90s, gravitated towards stability and harmony, a response to the tumult that defined their childhoods. To get them talking about their own memories of the holidays, we picked two films to watch with them.
It Happened on Fifth Avenue
An often forgotten Oscar nominee for Best Original Story, this is the film Frank Capra was planning to direct before he got pulled in to It’s a Wonderful Life.
The Story: A homeless man named Aloysius moves into the swanky Manhattan mansion of a business mogul after he heads south for the holidays, something he does every year — unbeknownst to the tycoon. This year, he invites a recently evicted World War II vet and a few of his war buddies to move in with him, and soon they’re joined by the tycoon’s daughter, who doesn’t let on who she is. There’s romance, reconnection, and a reckoning when the tycoon returns, as he comes face to face with the trespassers…and the plights of those living in the shadows of his wealth.
What it reveals about the Silent Generation: While it’s a comedy, It Happened on Fifth Avenue weaves in the realities of post-war America, including the growing gulf between rich and poor and the challenges that faced veterans. The film is also full of some of the language and cliches of the era, some cringe-y by today’s standards, but you’ll get a window into what the elders were raised on.
Where to stream it: Google Play, Amazon Prime, Apple TV, YouTube
Miracle on 34th Street (1947)
This perennial favorite actually won the Oscar for Best Original Story in 1947 over It Happened on Fifth Avenue, which might explain why it’s better known. Today, most younger people are more familiar with the film’s adaptations (1973 and 1994), but the original is the one to watch to be transported back to the era.
The Story: A man who goes by the name Kris Kringle (Edmund Gwenn) convinces the head of the Macy’s Thanksgiving Parade, Doris (Maureen O’Hara) to let him fill in for her intoxicated Santa. When Kris becomes a hit, he gets hired to be the regular St. Nick at the Macy’s store in Manhattan. Then he starts insisting that he really is Santa Claus, leading to a court case to determine his mental health.
The ‘Silent’ insights: With nods to the cynicism and commercialism of the post-war boom, Miracle on 34th Street digs into the tensions between those who believe in the importance of symbols and faith in “the intangibles” versus those who believe people (including children) need to face the harsher realities of life. Yet it’s ultimately a film about remembering the importance of kindness and the benefits of believing in something greater than yourself, whatever that might be.
Where to stream the original Miracle on 34th Street: Free with ads on YouTube.
For the Boomers
Christmas in Connecticut (1945)
Before there were endless Hallmark holiday movies set in Connecticut, there was this G-rated box office hit starring the legendary Barbara Stanwyck, which was filmed using the same set as Bringing Up Baby.
The Story: Elizabeth Lane (Stanwyck) is a writer for Smart Housekeeping magazine, where she presents herself as the perfect “homemaker columnist.” She has the perfect husband and baby, and she can cook! Bake! Craft! She’s like a post-war Martha Stewart—except she’s not. She has no idea how to do any of that, she just knows how to write about all of it. Alone and in her cramped apartment in Manhattan. Her ruse is about to be exposed when her publisher decides to bring a war hero and his fiance to his house for a traditional holiday dinner, forcing Elizabeth to “marry” her friend and head to his farm in Connecticut. Hijinks ensue as she tries to keep up her charade while hiding her percolating feelings for Mr. War Hero.
The Boomer appeal: While the film was released just before Boomers were born, they were more likely to watch this one on TV each holiday season as the first generation to grow up with a living room set. The film also offers a more idyllic look at post-war America, and it will resonate more with their generation as it introduces one of the first self-made women on screen. (Boomers went on to embrace the archetype of single career women with iconic shows like That Girl, Mary Tyler Moore, Rhoda, and Laverne & Shirley). The comedic scenes are also lighthearted enough not to offend their own parents, including an iconic disastrous sleigh ride.
Where to stream Christmas in Connecticut: Max
The Holdovers (2023)
A brand new release and a Golden Globe nominee in the Best Comedy or Musical category, The Holdovers were written and directed by a Boomer: Alexander Payne, best known for Sideways and The Descendants.
The Story:
The Watercooler’s Felipe Patterson describes it as “a cross-generation watch that will tug at your heartstrings as it nurtures your hope.” It also transports you back to the 70s with intention; the era contributes to each character’s deep-seated issues. Patrick Ryan, a critic for USA Today, compared Holdovers to It’s a Wonderful Life, as both films grapple with troubled pasts and shattered dreams at Christmastime.
The Boomer appeal: 1970 was an important year for Boomers. Still in the thick of Vietnam, they were becoming increasingly disillusioned with the war, and many watched as family members came home broken – or never came home at all. The Holdovers reflects this reality while avoiding the despair, and Boomers will relish the 70s fashion, slang, and music.
Where to stream The Holdovers: Apple+
For Gen X
Scrooged (1988)
A very 1980s retelling of A Christmas Carol that showcases all of the good and bad cliches of the era.
The Story: Frank Cross (Bill Murray) is a cynical TV executive who creates the most terrifying television ad for A Christmas Carol ever seen. In the wake of it, he visits three different ghosts, but they’re all amped-up 80s versions, like Carol Kane as the exuberant Ghost of Christmas Present. Unlike other holiday movie classics, Scrooged makes it clear that CEOs actually do love the holidays. Of course, it’s because they’re a cash cow. It’s also questionable how much Frank has changed by the end, but that will remind you of the arc of the 80s. You can also expect some throwback stereotyping, but it’s a film that will make you realize how far we’ve all come. And it unexpectedly sweetens, like a burnt gingerbread cookie.
The Gen X appeal: Beyond the sheer amount of 80s actors who pop up, including Carol Kane, Lee Majors, and Karen Allen, Scrooged captures the nihilism of the time, and it works as a satire of the Christmas entertainment that came before it. Parodies were at their peak during the late 80s.
Where to stream Scrooged: Paramount Plus, Amazon Prime
Babes in Toyland (1986)
There are actually three very different versions of Babes in Toyland, 1934 Laurel and Hardy classic, a 1961 film starring 
Annette Funicello, and the definitely-made-in-the-80s remake version starring a young Drew Barrymore and Keanu Reeves. For the Gen-X watch, queue up the latter. The Story: Eleven-year-old Lisa (Barrymore) is too busy taking care of her younger siblings to play with toys. But one day she ends up transported into a Disney-esque fantasy land, where she tries to stop a wedding between the mean old Barnaby Barnacle and a young Mary Contrary, who loves Jack Be Nimble. The Gen-X appeal: Watching baby faced Drew and Keanu appear in a movie that feels like watching your school musical, from the sets to the lines to the acting. Yet the “homemade” 80s effect is also what makes this one feel like “the end of innocence.”
Where to stream Babes in Toyland: Stream it for free on the Roku Channel or Pluto.
Less Than Zero (1987)
What I would loosely describe as “an expose on the hollow superficiality of the 1980s,” Less Than Zero is not your typical holly-jolly movie. It’s also not exactly relatable, as it’s about the decadence and overindulgence of wealthy, young Los Angelenos. But it stars three now iconic Gen X actors and captures some of the roots of “the lost generation.”
The Story: Based on the novel of the same name by Bret Easton Ellis, Clay (Andrew McCarthy), a college freshman, returns home for the holidays after a semester on the East Coast. Things aren’t quite as he remembered: his ex-girlfriend, Blair (Jami Getz) is now addicted to cocaine and sleeping with his high school best friend, Julian (Robert Downey Jr.), who’s also on drugs, and owes a lot of money to his dealer (James Spader). While Clay is technically the protagonist, the film’s story is mostly centered around Julian, who progressively deteriorates. The film’s seductive, lush world and upbeat dance-thump music contrast with the downward spiral of the characters, who, despite having everything, ultimately have nothing. Interestingly, Bret Easton Ellis did not care for the adaptation of his novel, but Downey impressed him with his performance. As Julian, Downey is far from the cocky likes of Tony Stark. This is Downey at his most raw, which we haven’t seen since, well, the 80s.
The Gen X factor: Less Than Zero captures some of the sharper changes of the 80s, a decade that became known for a collective obsession with money and all its trappings. This is when Gen-X was growing up, and while very few were living the life of these characters, the movie makes a point about how the rampant materialism of the era shaped the kids. It also throws into stark relief the “tough love” approach of Gen-Z parents and the spiraling that often occurred in their wake.
Where to find it: Starz
For Millennials
The Night Before (2017)
Let’s face it: we older millennials are now staring down the barrel of middle age, which means our holiday traditions are changing. Accepting change is one of the themes in The Night Before.
The Story: Three best friends — played by Joseph Gordon-Levitt, Seth Rogen, and Anthony Mackie — set out to find the elusive Nutcracker Ball. The trio have spent several Christmases together before this particular one, which marks the last time they’ll get into holiday shenanigans. While there are plenty of hijinks, including what may be the best karaoke scene included in a holiday movie, the heart of The Night Before is the idea that yes, getting older is hard and it forces us to change. But that doesn’t mean your friends have to fall by the wayside. You just may just do karaoke at home instead of a bar.
The Millennial appeal: Seth Rogen and Evan Goldberg wrote several millennial classics, including 50/50 and Superbad, and The Night Before incorporates their off kilter humor and oddball characters. At the same time, the film reflects concerns millennials are currently experiencing: how will our friendships look now that so many of us married and having children? As an added bonus, you’ll spot several actors who’ve become generational favorites: Look for Randall Park, Mindy Kaling, Lizzy Caplan, Ilana Glazer, and Michael Shannon in small roles.
Where to find it: Tubi
Christmas Comes Twice (2020)
As we face the prospect of middle age, we start to think about what could have been. In Christmas Comes Twice, our heroine literally goes back in time (only five years) to discover how, with a few changes, her life could have turned out.
The Story: Cheryl (Tamera Mowry) is an astrophysicist who, after taking a ride on a carousel, discovers she’s gone back in time. She reconnects with her beloved science teacher (Abbott Elementary’s Sheryl Lee Ralph, which makes me think this film takes place in the Abbott Elementary universe) and her frenemy, George (Michael Xavier). Is this a cheesy Hallmark that’s borderline cringe? Yes, but it also has a cute twist and a good lesson.
The Millennial appeal: As the generation that craves “do overs,” especially for the past five years, this will appeal to a generation worrying they’ve missed the boat. But it’s also a wakeup call that, hey, you’ve still got time to change your life!
Where to find it: Hulu
For Gen Z
Aggretsuko: We Wish You a Metal Christmas (2018)
If you worry that your Instagram isn’t getting enough likes or that you don’t have a date for the holidays, then this special based on the brilliant Japanese adult anime series is for you.
The Story: Aggretsuko is a red panda who takes out her aggression by singing death metal at karaoke. In the special, Retsuko learns that she has to work on Christmas Eve, and decide to try and fake the perfect Christmas. The pressure to appear to be having a wonderful Christmas time gets to her, and she quickly spirals. It may be one of the most relatable holiday specials ever made. If you’re feeling stressed about the holidays, maybe set your phone down for a bit and spend some time with your plants…like Retsuko’s coworker.
The Gen-Z hook: Retsuko’s life is a struggle to find work-life balance and channel the pressures she’s facing in her career as an accountant, and the prospect of her job going to an AI. Timely issues for everyone, but the focus on keeping up appearances while struggling with mental health will hit home with Gen Z.
Where to find it: Netflix
Ghosting: The Spirit of Christmas (2019)
Do more holiday movies need to have the protagonist die, become a ghost, meet up with their best friend, and try to track down the person they accidentally ghosted due to their death? According to Ghosting: The Spirit of Christmas, a wild holiday rom-com, that would be yes.
The Story: After an amazing first date with Ben (Kendrick Sampson), Jess (Aisha Dee) gets into a car accident and dies. Only Ben and her bestie Kara (Kimiko Glenn) can see her, and Jess and Kara assume the way to “ascend” is to find true love with Ben. Rather than relying on sugar, Ghosting has some bitters. But its macabre story and ending (no spoilers here!) give it a refreshing twist. And it still has plenty of cheeseball moments, like a hook up at a winter solstice. Oh, and we love a good literal ghosting theme.
The Gen Z hook: The mashup of the gothic and the romantic will appeal to the generation that helped make Addams family spinoff Wednesday such a hit.
Where to find it: Fubo (free)
Start a watercooler conversation: