Each year, as the air turns cold and the music merry, comes the inevitable debate about the best Christmas movies to stream during the holidays. There are those who insist their yuletide entertainment be staunchly seasonal—think the candy-coated North Pole of The Santa Clause franchise or Will Ferrell’s Buddy the Elf skipping through a department store. Others prefer films that take a more unconventional approach to the festivities, such as the action-packed Die Hard or erotically existential Eyes Wide Shut. Enter Vanity Fair’s Christmas favorites, 65 offerings that span from certified classics of the 1940s to new holiday movies destined for a yearly rewatch—a little something for everyone under the tree.

The Holdovers

• Release Year: 2023
• Director: Alexander Payne
• Noteworthy Cast: Paul Giamatti, Da’Vine Joy Randolph, Dominic Sessa, Carrie Preston

“I just don’t see it as a Christmas movie,” filmmaker Alexander Payne told Vanity Fair of his latest, which stars Paul Giamatti, Da’Vine Joy Randolph, and newcomer Dominic Sessa as three lost souls stranded at a New England prep school over the holidays. “It’s a movie that could take place only at Christmas because of the nature of it,” sure—but when the director sees “some early reviews like, ‘Oh, people will watch this every Christmas,’ I’m like, ‘Really? Great.’ But I didn’t think about that.” Nevertheless, it’s difficult to watch The Holdovers, written by David Hemingson, without sinking into its seasonal setting—complete with snow-covered windowpanes and 1970s holiday needle drops.

Santa Camp

• Release Year: 2022
• Director: Nick Sweeney

Leave any preconceived ideas about a Santa-centric documentary at the door. Centered on a New Hampshire campsite where professional Santas, Mrs. Clauses, and elves train to be experts in jolly, the film is actually all about how these mystical creatures get packaged and sold in society—in an upbeat, cheerful sort of way. Much of the doc confronts Santa’s diversity problem, told through the lens of a Black Santa, a transgender Santa, and a Santa with special needs who all attend the training program in hopes of disrupting a mythology that has largely embraced just elderly white men.

Falling for Christmas

• Release Year: 2022
• Director: Janeen Damian
• Noteworthy Cast: Lindsay Lohan, Chord Overstreet, George Young, Olivia Perez

Sure, it’s a fairly by-the-numbers tale in which a hotel heiress recovers from head-injury-induced amnesia at a cozy but struggling lodge owned by a charming widower. But this Netflix rom-com featuring Glee’s Chord Overstreet has one important factor working in its favor: the long-awaited return of Lindsay Lohan as leading lady. It’s best to just lean into the plot’s lunacy and let its smoothing seasonal magic take hold. You won’t be alone—the movie became a certified hit on streaming, earning more than 31.2 million views in its first four days of release.

Three Wise Men and a Baby

• Release Year: 2022
• Director: Terry Ingram
• Noteworthy Cast: Paul Campbell, Tyler Hynes, Andrew W. Walker, Margaret Colin

Determining which of Hallmark’s many, many holiday offerings are worth watching is an art form in and of itself. But cornball title aside, this Christmas-themed take on the hit 1987 comedy is one of the network’s best in recent years. Resident Hallmark hunks Andrew W. Walker, Tyler Hynes, and Paul Campbell (also a cowriter with fellow network regular Kimberley Sustad) play the Brenner brothers, who must put aside familial discord to raise a baby who gets unexpectedly placed in their path. Everyone, including their mother—played by the original film’s Margaret Colin—is playfully aware of how outlandish this premise is. That allows the audience to have fun with it too, so much so that it became cable’s most-watched movie of 2022 upon debut.

Single All the Way 

• Release Year: 2021
• Director: Michael Mayer
• Noteworthy Cast: Michael Urie, Philemon Chambers, Luke Macfarlane, Jennifer Coolidge

When Luke Macfarlane booked this film, following dozens of leading roles on Hallmark but before the release of his R-rated Bros, which features multiple Christmastime scenes, he found himself in hot water. As Macfarlane told Vanity Fair, people behind both Bros and his Hallmark titles were “not happy” that he had dipped his toe somewhere in between the two. Perhaps that’s the best way to describe the delicate tone of Netflix’s queer rom-com, which toes the line between raunchy humor and sentimental realism. Michael Urie’s Peter and Philemon Chambers’s Nick are longtime friends whose relationship teeters on the edge of romance just before they pose as real-life partners to smooth things over during a trip to visit Peter’s overbearing family. It also includes a star turn from Jennifer Coolidge as scene-stealing Aunt Sandy, who has a far more copacetic dynamic with these gays than the ones she (correctly) accused of trying to murder her in season two of The White Lotus.

Love Hard 

• Release Year: 2021
• Director: Hernán Jiménez
• Noteworthy Cast: Nina Dobrev, Jimmy O. Yang, Darren Barnet, Harry Shum Jr., James Saito

Catfishing during Christmastime serves as the focal point for this R-rated holiday rom-com starring Nina Dobrev as a writer who learns she’s being scammed when she flies 3,000 miles to visit her online paramour (posing as Darren Barnett, though he’s actually Jimmy O. Yang). 

Jingle Jangle: A Christmas Journey 

• Release Year: 2020
• Director: David E. Talbert
• Noteworthy Cast: Forest Whitaker, Madalen Mills, Keegan-Michael Key, Anika Noni Rose

Jingle Jangle: A Christmas Journey offers a little something for everyone under the tree—there’s sweeping gospel and R&B musical sequences, dazzling visual effects involving toys for the kiddies, and truly staggering performances from the likes of Forest Whitaker and Anika Noni Rose. 

Holidate

• Release Year: 2020
• Director: John Whitesell
• Noteworthy Cast: Emma Roberts, Luke Bracey, Kristin Chenoweth, Frances Fisher

Only some of Holidate’s chaotic premise takes place during Christmas. Sloane (Emma Roberts) and Jackson (Luke Bracey) actually spend a full calendar year as each other’s decoy dates, attending St. Patrick’s Day pub crawls and Fourth of July barbecues as each other’s plus-ones. But during their deal to spend big holidays by each other’s side, the prospect of keeping things platonic quickly begins to dwindle. 

Happiest Season

• Release Year: 2020
• Director: Clea DuVall 
• Noteworthy Cast: Kristen Stewart, Mackenzie Davis, Dan Levy, Aubrey Plaza

After reaching the pinnacle of blockbuster fame with Twilight, Kristen Stewart retreated into smaller indie dramas. But the tides began to shift back in recent years, with her high-profile role as Princess Diana in Spencer and her leading role in this upbeat holiday rom-com. She stars as Abby opposite Mackenzie Davis’s Harper. The pair are newly engaged and happier than ever when Harper drops the bomb that her family—whose home at which they’re spending the holidays—doesn’t know that she’s gay. Acting as roommates leads to inevitable conflict, featuring standout comedic performances from Dan Levy, Aubrey Plaza, and Mary Steenburgen.

Hustlers

• Release Year: 2019
• Director: Lorene Scafaria
• Noteworthy Cast: Constance Wu, Jennifer Lopez, Keke Palmer, Lilli Reinhart

Loosely based on a real credit card scam that exotic dancers ran on strip club patrons in New York, Hustlers tells the story of Ramona (Jennifer Lopez) and her mentorship of new dancer Dorothy (Constance Wu). A Christmas celebration featuring gifts acquired through the robbery of horny Wall Street guys is a peak moment.

The Princess Switch

• Release Year: 2018
• Director: Mike Rohl
• Noteworthy Cast: Vanessa Hudgens, Vanessa Hudgens (again), Sam Palladio, Nick Sagar

If you’re going to watch a far-fetched Netflix romantic comedy, why not go for the one in which Vanessa Hudgens stars as identical women—one royal, the other a baker living in Chicago—who switch lives and fall in love during the holiday season. Naturally, Hudgens upped the ante for subsequent films—playing three different characters in both 2020’s The Princess Switch: Switched Again and 2021’s The Princess Switch 3: Romancing The Star. 

The Man Who Invented Christmas

• Release Year: 2017
• Director: Bharat Nalluri
• Noteworthy Cast: Dan Stevens, Christopher Plummer, Jonathan Pryce

A Christmas Carol is one of the most frequently revisited and reinterpreted holiday stories of all time; but how did it come to be? The Man Who Invented Christmas follows Charles Dickens (Dan Stevens) as he tries to bounce back from several recent creative and financial failures. While writing A Christmas Carol on a tight and inflexible deadline, his characters appear to interact with him, including his protagonist, Ebenezer Scrooge (Christopher Plummer).

A Bad Moms Christmas

• Release Year: 2017
• Director: Jon Lucas and Scott Moore
• Noteworthy Cast: Mila Kunis, Kristen Bell, Kathryn Hahn, Christine Baranski, Cheryl Hines, Susan Sarandon

Jon Lucas and Scott Moore’s 2016 comedy Bad Moms was a surprise runaway hit, grossing more than $113 million on a $20 million budget. A holiday-themed sequel was rushed into production for release 17 months later, and features double the maternal star-wattage. Amy (Mila Kunis), Kiki (Kristen Bell), and Carla (Kathryn Hahn) have to navigate the most stressful season of the year for mothers while juggling the arrival of their own mommies dearest: Amy’s mother, Ruth (Christine Baranski); Kiki’s mother, Sandy (Cheryl Hines); and Carla’s mother, Isis (Susan Sarandon).

Almost Christmas

• Release Year: 2016
• Director: David E. Talbert
• Noteworthy Cast: Danny Glover, Kimberly Elise, Gabrielle Union, Romany Malco, Nicole Ari Parker, Mo’Nique

Retired widower Walter (Danny Glover) is hosting his first Christmas since the death of his wife. His goal is to put on a traditional holiday celebration, but his fractious adult children—played by Kimberly Elise, Gabrielle Union, Romany Malco, and Jessie Usher—may scuttle his plans with their bickering.

Office Christmas Party

• Release Year: 2016
• Director: Josh Gordon and Will Speck
• Noteworthy Cast: Jennifer Aniston, Jason Bateman, T.J. Miller, Kate McKinnon, Olivia Munn

Most holiday gatherings among coworkers contain stilted conversation, stale passed appetizers, and an unspoken agreement about how many trips to the spiked punch bowl are too many with the boss close by. But the cinematic version of this time-honored tradition is a far raunchier, more inebriated ode to the corporate pastime that features an all-star cast of employees led by Jennifer Aniston, Jason Bateman, T.J. Miller, Kate McKinnon, and Olivia Munn. 

The Night Before

• Release Year: 2015
• Director: Jonathan Levine
• Noteworthy Cast: Seth Rogen, Anthony Mackie, Joseph Gordon-Levitt, Lizzy Caplan

Three lifelong friends (Seth Rogen, Anthony Mackie, Joseph Gordon-Levitt) venture to spend one last rollicking Christmas Eve in New York City together before adult responsibilities intervene. Their holiday wish comes true—and then some, thanks to the antics of Michael Shannon, Ilana Glazer, and a pre-Rehearsal Nathan Fielder.

Carol

• Release Year: 2015
• Director: Todd Haynes
• Noteworthy Cast: Cate Blanchett, Rooney Mara, Jake Lacy, Kyle Chandler, Sarah Paulson

Aspiring photographer Therese (Rooney Mara) is spending the Christmas of 1952 working in a Manhattan department store and dating Richard (Jake Lacy). She’s already been putting off his suggestions that they get married when the elegant, bewitching Carol (Cate Blanchett) walks up to Therese’s counter at the store and changes her life forever.

Krampus

• Release Year: 2015
• Director: Michael Dougherty
• Noteworthy Cast: Adam Scott, Toni Collette, Emjay Anthony

The chaotic Engel family assembles for Christmas, primarily to fight and ruin the holiday for Max (Emjay Anthony)—the only member young enough still to believe in Santa Claus. When his frustration leads him to tear up his letter to Santa and scatter it to the winds, he summons Santa’s antithesis: Krampus, a demon that proceeds to terrorize the family. If you feel like watching a holiday movie but your favorite film of 2019 was Midsommar, give Krampus a look.

The Best Man Holiday

• Release Year: 2013
• Director: Malcolm D. Lee
• Noteworthy Cast: Taye Diggs, Morris Chestunt, Terrence Howard, Regina Hall

In this sequel to 1999’s The Best Man, Mia (Monica Calhoun) and her husband Lance (Morris Chestnut) invite their old college friends to spend Christmas with them at their lavish home—the first time they’ve all been together since the events of The Best Man. Some old tensions resurface, which may be why only Harper (Taye Diggs) notices that Mia has lost a lot of weight and doesn’t seem to be feeling well….

Arthur Christmas

• Release Year: 2011
• Director: Sarah Smith and Barry Cook
• Noteworthy Cast: James McAvoy, Bill Nighy, Jim Broadbent, Hugh Laurie

Aardman Animations, of Wallace and Gromit fame, is one of the studios that brings us this take on North Pole operations. Sitting Santa Malcolm Claus (voice of Jim Broadbent) supervises while his son and presumed successor Steve (Hugh Laurie) runs deliveries with military efficiency. Steve’s younger brother Arthur (James McAvoy) answers letters. But when Steve and Arthur argue over whether one missed gift is an acceptable screw-up, Arthur goes rogue, determined to make it right despite his total lack of experience.

In Bruges

• Release Year: 2008
• Director: Martin McDonagh
• Noteworthy Cast: Colin Farrell, Brendan Gleeson, Ralph Fiennes

Nearly 15 years before they’d reunite—and earn Oscar nominations—as former best friends in The Banshees of Inisherin, Colin Farrell and Brendan Gleeson took cover in Martin McDonagh’s feature-film debut. Set during Christmastime, Farrell is Ray, an amateur hit man who accidentally kills a child while purposely killing a priest. His far more experienced partner is Gleeson’s Ken, with whom he hunkers down in the historic Belgian town of Bruges to shelter while their boss Harry (Ralph Fiennes) decides their fate.

Four Christmases

• Release Year: 2008
• Director: Seth Gordon
• Noteworthy Cast: Vince Vaughn, Reese Witherspoon, Sissy Spacek, Robert Duvall

Because each of their four parents has divorced, remarried, and created stressful new households, Brad (Vince Vaughn) and Kate (Reese Witherspoon) have always escaped familial obligations by planning glamorous travel and claiming they’re doing charity work. But when a weather system cancels their flight so disastrously that they’re interviewed about it on TV, all their parents learn that they’ll be staying in the contiguous U.S.—and they have to strain their own relationship by visiting all their families.

This Christmas

• Release Year: 2007
• Director: Preston A. Whitmore II
• Noteworthy Cast: Regina King, Idris Elba, Delroy Lindo, Loretta Devine

The Whitfield family’s first Christmas together in four years is soon eroded by familial infighting, closely-guarded secrets, and the wear and tear of distance. An all-star cast led by Loretta Devine, Idris Elba, Columbus Short, Delroy Lindo, and Regina King makes this a holiday film worth unwrapping year after year. 

The Holiday

• Release Year: 2006
• Director: Nancy Meyers
• Noteworthy Cast: Cameron Diaz, Kate Winslet, Jude Law, Jack Black, Eli Wallach

London wedding columnist Iris (Kate Winslet) is shattered when Jasper (Rufus Sewell), with whom she’s been having an on-and-off affair for several years, announces his engagement to another woman. She’s weeping at home when she gets a message through a home exchange service: Amanda (Cameron Diaz) wants to get out of Los Angeles for the holidays, and they agree to trade homes. In England, Amanda crosses paths with Iris’s hot, hard-drinking brother Graham (Jude Law), while Iris gets close to Amanda’s retired screenwriter neighbor Arthur (Eli Wallach) and goofy film score composer Miles (Jack Black). A fine work from Nancy Meyers, maestro of wealthy women’s romantic struggles.

Kiss Kiss Bang Bang

• Release Year: 2005
• Director: Shane Black
• Noteworthy Cast: Robert Downey Jr., Val Kilmer, Michelle Monaghan

A series of mishaps and misunderstandings bring burglar Harry (Robert Downey Jr.) from a botched job in New York to an audition, and then a party, in Los Angeles (at Christmastime!). It turns out to be a fateful affair for Harry: he meets PI “Gay” Perry (Val Kilmer) and reunites with his childhood crush Harmony (Michelle Monaghan), and the three of them get snarled up in a complicated caper.

The Family Stone

• Release Year: 2005
• Director: Thomas Bezucha
• Noteworthy Cast: Sarah Jessica Parker, Diane Keaton, Rachel McAdams, Luke Wilson

Everett Stone (Dermot Mulroney) is bringing his girlfriend Meredith (Sarah Jessica Parker) to spend Christmas with his family. But as warm as they can be, Meredith is so nervous she makes a terrible impression. Everett’s sister Amy (Rachel McAdams) already has her knives out after meeting Meredith once before; Everett’s mother Sybil (Diane Keaton) fears he’s going to ask her for an heirloom engagement ring to propose to Meredith; and things only get worse when Meredith begs her sister Julie (Claire Danes) to come give her moral support, and all the Stones like Julie better—possibly including Everett.

Christmas with the Kranks

• Release Year: 2004
• Director: Joe Roth
• Noteworthy Cast: Jamie Lee Curtis, Tim Allen, Dan Aykroyd

In an adaptation of John Grisham’s 2001 novel Skipping Christmas, Jamie Lee Curtis and Tim Allen star as a well-meaning couple who opt to do just that. But it’s not long before their suburban neighbors catch wind of their plan to trade tinsel and holly for a tropical vacation—and do everything in their power to stop it. 

Mean Girls

• Release Year: 2004
• Director: Mark Waters
• Noteworthy Cast: Lindsay Lohan, Rachel McAdams, Lacey Chabert, Amanda Seyfried

Long before there was the Mean Girls musical (which, yes, does contain actual music), there was a lascivious dance performance to “Jingle Bell Rock” at a Christmas assembly in the original 2004 film. It’s a major dynamic-shifting sequence in the film, as the previously uncool Cady (Lindsay Lohan) rises in the ranks to become Regina George’s (Rachel McAdams) best friend over fellow Plastics Gretchen Weiners (future Hallmark Christmas queen Lacey Chabert) and Karen Smith (Amanda Seyfried). The scene became so iconic that it got recreated in the music for Ariana Grande’s “Thank U, Next,” featuring Grande as Regina, her Victorious costar Elizabeth Gillies as Cady, and Kris Jenner as Amy Poehler’s “Cool Mom.”

The Polar Express

• Release Year: 2004
• Director: Robert Zemeckis
• Noteworthy Cast: Tom Hanks (over and over again)

Robert Zemeckis is known for visual spectacle, from Back to the Future to Death Becomes Her, but nothing scratches a particular seasonal itch like his adaptation of a seminal picture book written and illustrated by Chris Van Allsburg. For however strange you remember this film being, it’s worth revisiting as a reminder that Tom Hanks expertly, eerily shifts between six different roles; that an earworm of a “Hot Chocolate” song is way better than it has any right to be; and that Zemeckis’s Jim Carrey–led take on A Christmas Carol in 2009 could never match the mystical oddities of The Polar Express.

Elf

• Release Year: 2003
• Director: Jon Favreau 
• Noteworthy Cast: Will Ferrell, Zooey Deschanel, James Caan, Mary Steenburgen, Bob Newhart

It becomes clear minutes into Jon Favreau’s sophomore directorial feature that Buddy (Will Ferrell) will never quite fit with the other elves at the North Pole, both because of his physical size and toy-making ineptitude. Why? Because he’s human, as Buddy learns from his Papa Elf (Bob Newhart), who adopted and raised him. In the search for his greater purpose, Buddy takes a mystical journey to meet his biological father, Walter (James Caan), in New York City, a land rife with treasures including “the world’s best cup of coffee” and part-time Gimbels elf Jovie (Zooey Deschanel).

Eloise at Christmastime

• Release Year: 2003
• Director: Kevin Lima
• Noteworthy Cast: Sofia Vassilieva, Julie Andrews, Christine Baranski, Gavin Creel

This under-the-radar gem, aired by ABC and Walt Disney Studios as a follow-up to 2003’s Eloise at the Plaza, was adapted from Kay Thompson and Hilary Knight’s beloved children’s books. Sofia Vassilieva stars as a holiday-obsessed Eloise, who celebrates the season at the Plaza alongside her doting if occasionally disapproving nanny, played by Julie Andrews. The whimsical picture books are brought to delightful life, thanks in part to a musical subplot featuring Tony-winning actor Gavin Creel as Bill, a bellhop and aspiring actor who acts out songs with Eloise. As lensed by Kevin Lima, who went on to direct Amy Adams in Enchanted, the musical moments are among the movie’s best.

Love Actually

• Release Year: 2003
• Director: Richard Curtis
• Noteworthy Cast: Hugh Grant, Colin Firth, Keira Knightley, Emma Thompson, Alan Rickman, Liam Neeson

Why do we still love Love Actually? Maybe it’s the way the film melds tragedy and comedy. As Vanity Fair’s Katey Rich noted on the film’s 20th anniversary, Love Actually boasts a “dogged optimism that in the face of awfulness—the death of a spouse, infidelity, inexplicably being called fat by your loved ones—the human spirit can prevail.” This is evident in a number of the love stories that play out against the backdrop of London at Christmastime. Karen (Emma Thompson) has no idea her husband Harry (Alan Rickman) is flirting with his new assistant, Mia (Heike Makatsch); Mark (Andrew Lincoln) is tortured by his obsession with Juliet (Keira Knightley), despite having just stood up as best man at her wedding to his friend Peter (Chiwetel Ejiofor); the prime minister (Hugh Grant) is drawn to a household staffer (Martine McCutcheon), problematic work dynamics aside; a grieving father (Liam Neeson) and son (Thomas Brodie-Sangster) conspire to make his schoolyard crush a reality; and so on, until we see at the end how they all wildly interconnect.

Bad Santa

• Release Year: 2003
• Director: Terry Zwigoff
• Noteworthy Cast: Billy Bob Thornton, Brett Kelly, Bernie Mac, Lauren Graham, John Ritter

Upbeat, making-spirits-bright holiday fare isn’t hard to find. But some of the best Christmas movies place themselves squarely on the naughty list, perhaps none more than 2003’s R-rated take on St. Nick. Billy Bob Thornton stars as a Kris Kringle who spews profanity, beds women, and guzzles cocktails all while wearing a Santa suit. The 2016 sequel pales in comparison to the first, although it does feature scene-stealing work from Kathy Bates and Christina Hendricks.

The Santa Clause 2

• Release Year: 2002
• Director: Michael Lembeck 
• Noteworthy Cast: Tim Allen, Elizabeth Mitchell, Eric Lloyd, David Krumholtz, Molly Shannon

A few years after Tim Allen’s Scott Calvin becomes ‘ole St. Nick, he’s tasked with meeting his Mrs. Claus—and he unexpectedly finds her in the anti-holiday cheer principal of his son’s school, played by Elizabeth Mitchell.  A key part of their courtship? Giving her the present she never got as a child, of course. 

About A Boy

• Release Year: 2002
• Director: Chris Weitz and Paul Weitz
• Noteworthy Cast: Hugh Grant, Nicholas Hoult, Toni Collette, Rachel Weisz

Will (Hugh Grant) has never had to work, thanks to his father’s having written “Santa’s Super Sleigh,” a tremendously popular Christmas song. His comfortable life is entirely unencumbered until he crosses paths with Marcus (Nicholas Hoult), a lonely nerd who’s justly anxious about his mother Fiona (Toni Collette), who has depression. Will and Marcus become friends, but when Will mentions him to new romantic prospect Rachel (Rachel Weisz) and she assumes he’s Marcus’s father, things get complicated.

Eyes Wide Shut

• Release Year: 1999
• Director: Stanley Kubrick
• Noteworthy Cast: Tom Cruise, Nicole Kidman, Sydney Pollack, Vinessa Shaw

“Erotic thriller” may not be the first film genre you reach for during the holidays, but this one is set at Christmas. In the final film from director Stanley Kubrick, New York City doctor Bill Harford (Tom Cruise)—shocked and destabilized after his wife, Alice (Nicole Kidman), reveals that she once almost had an affair—leaves their home and takes a dreamy trip through the city’s lurid sexual underworld.

Go

• Release Year: 1999
• Director: Doug Liman
• Noteworthy Cast: Sarah Polley, Katie Holmes, Timothy Olyphant

Director Doug Liman followed his surprise hit Swingers with this film, set at Christmas in Los Angeles. Supermarket clerk Ronna (Sarah Polley), trying to avoid eviction, pursues a lead to sell ecstasy to a couple of strangers while her co-worker—the actual dealer they were looking for—is out of town. The story spirals outward into several other plots involving a rave, a couple of closeted soap actors, a comedy of errors in Las Vegas, and a shirtless Timothy Olyphant.

Stepmom

• Release Year: 1998
• Director: Chris Columbus
• Noteworthy Cast: Susan Sarandon, Julia Roberts, Ed Harris, Jena Malone, Liam Aiken

Isabel (Julia Roberts) loves her boyfriend Luke (Ed Harris), but feels inadequate compared to his effortlessly competent ex-wife Jackie (Susan Sarandon). While Isabel has a good relationship with Luke’s son Ben (Liam Aiken), his daughter Anna (Jena Malone) is relentlessly hostile. Jackie and Isabel have already clashed over parenting when Luke puts more stress on their relationship by proposing marriage to Isabel. Then Jackie finds out she has terminal cancer, and realizes she not only has to accept Isabel, but prepare her to raise Jackie’s children when Jackie is gone.

Jingle All The Way

• Release Year: 1996
• Director: Brian Levant
• Noteworthy Cast: Arnold Schwarzenegger, Sinbad, Phil Hartman, Rita Wilson

Years before we all knew about problems with the consumer-goods supply chain, Jingle All The Way dared to address the agony of trying to track down the one toy your kid most desperately wants to find under the tree. Rival dads Howard (Arnold Schwarzenegger) and Myron (Sinbad) meet each other on the field of battle in pursuit of the year’s marquee toy: Turbo-Man.

The Preacher’s Wife

• Release Year: 1996
• Director: Penny Marshall
• Noteworthy Cast: Whitney Houston, Denzel Washington, Courtney B. Vance

New York pastor Henry (Courtney B. Vance) is struggling in his parish, given declining attendance and a compelling offer to sell the property to a developer. Henry prays for help, and soon meets Dudley (Denzel Washington), who tells Henry he’s the answer to his prayer, and a literal angel sent by God. Henry doubts Dudley’s story, but Henry’s wife Julia (Whitney Houston) is intrigued.

Miracle on 34th Street

• Release Year: 1994
• Director: Les Mayfield
• Noteworthy Cast: Mara Wilson, Richard Attenborough, Elizabeth Perkins, Dylan McDermott

Remakes of any kind are risky business, but perhaps none had more going against it than John Hughes’s take on this 1947 classic. But screenwriter Hughes and director Les Mayfield endeavored to reimagine a film that still gets watched on a yearly basis without even the approval of Macy’s department store (“Coles” is this version’s proxy). In doing so, they produced a perfectly heartfelt, slightly updated version with Elizabeth Perkins as the store event director; Richard Attenborough as Kris Kringle; and Mara Wilson as Susan. It’s a lesson in appreciating the original while still welcoming another iteration to the holiday film canon—if only to see a blink-and-you-missed-it Allison Janney as a sassy department store shopper.

The Santa Clause

• Release Year: 1994
• Director: John Pasquin
• Noteworthy Cast: Tim Allen, Eric Lloyd, Wendy Crewson, Judge Reinhold, David Krumholtz

The whole Santa Clause enterprise has become quite lucrative for Disney, with two increasingly big-budget sequels and a current streaming TV adaptation (though the less said about that, the better) that delves far, far into the lore of Santadom. But it’s the 1994 original that stands above the rest for its utter simplicity. Tim Allen is toy salesman Scott Calvin, a curmudgeonly single father who takes his kid to Denny’s for Christmas Eve dinner hours before a clatter on the roof changes his life forever. When Santa topples from the roof, Calvin finds a card in his suit pocket, which indicates that the reindeer will know what to do, and…long story short, Scott has to become the new Santa Claus.

The Nightmare Before Christmas

• Release Year: 1993
• Director: Henry Selick
• Noteworthy Cast: Chris Sarandon, Catherine O’Hara, Paul Reubens

Jack Skellington (Chris Sarandon when speaking; Danny Elfman singing) has been experiencing increasing ennui in his life as the Pumpkin King of Halloween Town. Then he chances into Christmas Town and, awed by what he sees, tries to bring the wonders of the holiday back to his fellow Halloween Town residents. When that fails, he decides to invade and occupy Christmas Town instead.

The Muppet Christmas Carol

• Release Year: 1992
• Director: Brian Henson
• Noteworthy Cast: Michael Caine, Frank Oz, Dave Goelz

Legendary curmudgeon Ebenezer Scrooge (Michael Caine) has no room in his heart for Christmas celebrations...until he is visited by several ghosts who try to change his ways by taking him through his Christmases past, present, and future. Because this is the Muppet Christmas Carol, Jacob and Robert Marley are Statler and Waldorf; Bob Cratchit is Kermit the Frog; and our narrator Charles Dickens is Gonzo.

Home Alone 2: Lost in New York

• Release Year: 1992
• Director: Chris Columbus
• Noteworthy Cast: Macaulay Culkin, Joe Pesci, Daniel Stern, Catherine O’Hara

Its shoddy New York geography aside, Home Alone 2: Lost in New York remains one of the most delightful holiday sequels ever made. The same can’t be said for subsequent follow-ups Home Alone 3, Home Alone 4: Taking Back the Heist, Home Alone: Five Lives, and Home Alone: The Holiday Heist. (Only one of those is made up.) 

Batman Returns

• Release Year: 1992
• Director: Tim Burton
• Noteworthy Cast: Michael Keaton, Michelle Pfeiffer, Danny DeVito, Christopher Walken

Gotham socialites Tucker and Esther Cobblepot (Paul Reubens and Diane Salinger) throw their physically disfigured child into a sewer, where he drifts into the zoo to be raised by penguins. Thirty-three years later, the former Oswald is now The Penguin (Danny DeVito), determined to scheme his way back into society by staging acts of heroism, but also blackmailing local millionaire Max Schreck (Christopher Walken). Schreck’s assistant Selina Kyle (Michelle Pfeiffer) stumbles upon compromising material; when he pushes her out a window, she discovers she has nine lives. It’s a gnarly plot, but basically: Batman (Michael Keaton) fights two villains, one of whom he’s attracted to, around Christmastime!

Edward Scissorhands

• Release Year: 1990
• Director: Tim Burton
• Noteworthy Cast: Johnny Depp, Winona Ryder, Dianne Wiest, Vincent Price

A reclusive inventor (Vincent Price) constructs and raises Edward (Johnny Depp), an artificial boy, but dies of a heart attack before he can replace with hands the scissors that have served that function all Edward’s life. Eventually, Edward is discovered by Peg (Dianne Wiest), an Avon lady, who brings Edward home to live with her. He doesn’t fit into her suburban neighborhood, but he is drawn to her daughter Kim (Winona Ryder).

Home Alone

• Release Year: 1990
• Director: Chris Columbus
• Noteworthy Cast: Macaulay Culkin, Joe Pesci, Daniel Stern, Catherine O’Hara

The large and noisy McCallister family gather at Peter (John Heard) and Kate’s (Catherine O’Hara) house the night before a trip to spend Christmas in Paris. A power outage knocks out everyone’s alarms, leading to a mad dash to the airport; not until Kate is seated on the plane does she realize they forgot her 8-year-old son, Kevin (Macaulay Culkin). While Kate scrambles to make her way back home, Kevin looks after himself and protects the house from burglars Harry (Joe Pesci) and Marv (Daniel Stern).

National Lampoon’s Christmas Vacation

• Release Year: 1989
• Director: Jeremiah S. Chechik 
• Noteworthy Cast: Chevy Chase, Beverly D’Angelo, Randy Quaid, Juliette Lewis, Johnny Galecki 

For those who grew up in a Christmas Vacation–watching household (hi there), this sequel to 1983’s Vacation remains one of the most quotable, rewatchable Christmas comedies of all time. Returning players Chevy Chase, Beverly D’Angelo, and Randy Quaid are reliably hilarious, but it’s the performances from Juliette Lewis and Johnny Galecki as their ever-traumatized children (roles recast in each Vacation film) that shine a bit more with each repeat viewing. Even the wealthy, buttoned-up next-door neighbors played by Julia Louis-Dreyfus and Nicholas Guest are now so beloved that their brief roles have spawned merch alongside the expected Griswold gear.

Die Hard

• Release Year: 1988
• Director: John McTiernan
• Noteworthy Cast: Bruce Willis, Alan Rickman, Bonnie Bedelia 

On Christmas Eve, New York City detective John McClane (Bruce Willis) reunites with his estranged wife Holly (Bonnie Bedelia) at her company’s holiday party atop the partially completed Nakatomi Tower. He’s freshening up after his flight when terrorists break in and start making demands; since they don’t know he’s there, John tries to use his stealth and ingenuity to save the hostages. And would you believe Die Hard 2: Die Harder also involves John McClane having a terrible Christmas Eve? 

Scrooged (1988)

• Release Year: 1988
• Director: Richard Donner
• Noteworthy Cast: Bill Murray, Alfre Woodard, Karen Allen

Frank Cross (Bill Murray) is a TV executive planning a garish adaptation of A Christmas Carol to air live on Christmas Eve. As he gets increasingly stressed, Frank is visited by the ghost of Lew Hayward (John Forsythe), his former mentor, who warns him that more ghosts will be walking him through the events of his life in order to change his heart. Alfre Woodard plays Grace, the Bob Cratchit stand-in, whose son hasn’t spoken since his father died; Karen Allen is Claire, a social worker and the ex-girlfriend Frank left behind in pursuit of his career.

Gremlins

• Release Year: 1984
• Director: Joe Dante
• Noteworthy Cast: Hoyt Axton, Zach Galligan, Phoebe Cates

Failed inventor Randall Peltzer (Hoyt Axton) thinks he’s found the perfect Christmas gift in a shop in Chinatown: a cuddly little creature called a mogwai. The shop owner (Keye Luke) tries to refuse to sell the mogwai, finally relenting after telling Rand the rules for its care: he must not expose it to sunlight or bright lights, let it get wet, and never feed it after midnight. Rand and his family will learn the hard way how important it is to follow these rules.

A Christmas Story

• Release Year: 1983
• Director: Bob Clark
• Noteworthy Cast: Peter Billingsley, Melinda Dillon, Scott Schwartz, Darren McGavin

Ralphie (Peter Billingsley) wants nothing more for Christmas than a Red Ryder Carbine Action 200-shot Range Model air rifle, and ignores the warnings of everyone he tells that he’ll “shoot [his] eye out.” During this particular Christmas journey, Ralphie’s friend Flick (Scott Schwartz) learns why you shouldn’t stick your tongue to cold metal; and Ralphie’s mother (Melinda Dillon) learns why she should pay more attention to which contests her husband (Darren McGavin) enters, lest he actually win a prize of a lamp shaped like a woman’s leg in a fishnet stocking.

Trading Places

• Release Year: 1983
• Director: John Landis
• Noteworthy Cast: Eddie Murphy, Dan Aykroyd, Ralph Bellamy, Jamie Lee Curtis

Not often properly recognized as a Christmastime film, Eddie Murphy and Dan Aykroyd star as two men who get embroiled in a financial scheme that requires Aykroyd to sport a Santa suit that has been through some things. 

How the Grinch Stole Christmas!

• Release Year: 1966
• Director: Chuck Jones and Ben Washam
• Noteworthy Cast: Boris Karloff, June Foray, Dal McKennon

There’s an inherent warmth in the original version of this tale—directed and coproduced by Looney Tunes veteran Chuck Jones, and with Boris Karloff voicing the titular character—that’s missing from every subsequent version. Ignore both 2018’s CGI animated version with Benedict Cumberbatch in the lead, and the 2000 live-action film starring Jim Carrey under prosthetics. It is the understated, 25-minute take on the creature with “a heart two sizes too small” that remains the most heartwarming of the bunch, and one of the reasons it gets re-aired yearly on broadcast TV decades after its debut.

A Charlie Brown Christmas

• Release Year: 1965
• Director: Bill Melendez
• Noteworthy Cast: Peter Robbins, Chris Doran, Sally Dryer

“Christmas Time Is Here” is the simple but soulful refrain at the center of this 1965 special, born when CBS asked producer Lee Mendelson if he could put together a holiday program in merely six months. As his son, Jason Mendelson, told CBS in 2021, “My father called [Peanuts creator] Charles Schulz and he said, ‘Hey, I just sold Charlie Brown Christmas to CBS. And Charles Schulz said, ‘What’s that?’ And my father said, ‘It’s something you and I have to write over the weekend!’” The result of this expedited process is astonishing. Voiced by Peter Robbins, Charlie Brown is depressed about his lack of Christmas spirit; when he chooses an anemic little tree from the lot, his so-called friends mock his choice. Can Linus’s recitation of the nativity story from the Book of Luke turn things around?

Babes in Toyland

• Release Year: 1961
• Director: Jack Donohue
• Noteworthy Cast: Tommy Sands, Annette Funicello, Ray Bolger, Ed Wynn

Once you get past the part where crooked miser Barnaby (Ray Bolger) tricks Mary Contrary (Annette Funicello) into marrying him after...first tricking her into marrying Tom Piper (Tommy Sands), who then gets kidnapped and falsely reported dead, this is a cute romp for kids! The toy soldier battle is an all-timer. And if you like it, you can stream the 1986 remake—starring Keanu Reeves and Drew Barrymore.

White Christmas

• Release Year: 1954
• Director: Michael Curtiz
• Noteworthy Cast: Bing Crosby, Danny Kaye, Rosemary Clooney, Vera-Ellen

Although Holiday Inn had the distinction of featuring a rendition of “White Christmas” first, this is the Bing Crosby–led musical set in a bucolic setting that most associate with the yuletide season. Crosby stars alongside Danny Kaye as a pair of singers who join forces with a sister song-and-dance act to put on a Christmas show in rural Vermont. To add even more confusion in differentiating this film from Holiday Inn, the foursome put on a show in order to save—what else—a financially failing country inn.

Miracle On 34th Street

• Release Year: 1947
• Director: George Seaton
• Noteworthy Cast: Edmund Gwenn, Natalie Wood, Maureen O’Hara

Macy’s event director and single mother Doris (Maureen O’Hara) has raised her daughter Susan (Natalie Wood) to be a clear-eyed pragmatist, which is why she’s shaken when the latest Macy’s Santa, Kris Kringle (Edmund Gwenn), convinces Susan that he really is Santa. 

It’s A Wonderful Life

• Release Year: 1946
• Director: Frank Capra
• Noteworthy Cast: James Stewart, Donna Reed, Lionel Barrymore, Henry Travers

On Christmas Eve 1945, George Bailey (James Stewart) prepares to die by suicide. His worried friends and loved ones, praying for him, activate Clarence (Henry Travers), a trainee angel who will earn his wings if he can prevent George from ending his life. We join Clarence as he watches vignettes from George’s earlier days to see what has brought George to such despair. (Don’t worry: it has a happy ending.)

Christmas in Connecticut

• Release Year: 1945
• Director: Peter Godfrey
• Noteworthy Cast: Barbara Stanwyck, Dennis Morgan, Sydney Greenstreet

Every Hallmark or Lifetime Christmas movie leading lady has, in some ways, been following Barbara Stanwyck’s lead as a woman finding domestic bliss beneath her career woman exterior in a film that charms, despite its dated ideas about femininity. 

Meet Me in St. Louis

• Release Year: 1944
• Director: Vincente Minnelli
• Noteworthy Cast: Judy Garland, Margaret O’Brien, Mary Astor, Tom Drake

This MGM musical is the type of Christmas film that other movies set during the season love to reference. In the first Sex and the City movie, Jennifer Hudson’s “Louise From St. Louis” gifts a copy of the DVD to Sarah Jessica Parker’s Carrie Bradshaw for her first holidays after Mr. Big has left her at the altar. In 2005’s The Family Stone, another film featuring SJP, Craig T. Nelson and Elizabeth Reaser’s characters share an emotional moment while watching Judy Garland croon “Have Yourself a Merry Little Christmas” in this movie. Their tears are justified, given the sweeping sadness at the center of her performance in a happy-go-lucky big-budget musical.

Holiday Inn

• Release Year: 1942
• Director: Mark Sandrich and Robert Allen
• Noteworthy Cast: Bing Crosby, Fred Astaire, Marjorie Reynolds

What some may not know is that 12 years before a full-fledged film was constructed around Irving Berlin’s “White Christmas,” it was actually sung for the first time onscreen in this classic big-screen musical. The whole feature is a showcase for Berlin’s music, as well as the song-and-dance stylings of Bing Crosby and Fred Astaire, who engage in a twisty love triangle with Marjorie Reynolds at a cozy country inn.

The Shop Around the Corner

• Release Year: 1940
• Director: Ernst Lubitsch
• Noteworthy Cast: James Stewart, Margaret Sullavan, Frank Morgan

“You know, people seldom go to the trouble of scratching the surface of things to find the inner truth,” a pre–It’s a Wonderful Life Jimmy Stewart tells his coworker and secret pen pal, played by Margaret Sullavan. She retorts, “Well, I really wouldn’t care to scratch your surface, Mr. Kralik, because I know exactly what I’d find: Instead of a heart, a hand-bag. Instead of a soul, a suitcase. And instead of an intellect, a cigarette lighter…which doesn’t work.” Sound familiar? It’s a quippy exchange recreated by Tom Hanks and Meg Ryan in 1998’s You’ve Got Mail. Nora Ephron adapted Ernst Lubitsch’s tale of feuding shop employees with a shielded romantic entanglement for a new generation—but her original inspiration is worth revisiting, no matter how many decades have passed.

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