Holiday Comedies We're Obsessed With

When you think of the perfect holiday movie, does your mind go straight to the classics like “It’s a Wonderful Life” or “A Christmas Carol”? Or are you one of those people who insists “Die Hard” is a Christmas movie (no judgment… okay, maybe a little). But for me, the ultimate holiday movies have always been comedies. Because nothing says “the holidays” quite like laughing your head off while the tree is lit and the snacks are within arm’s reach.

Let’s face it—the holidays can be a lot. There’s shopping, cooking, traveling, and navigating family dynamics that deserve their own screenplay. That’s why holiday comedies are such a gift. They’re warm, ridiculous, comforting, and endlessly rewatchable. These are the movies you put on while wrapping presents, quoting along with your favorite lines, and remembering why laughter is the best part of the season.

After my recent fabulous one-hour conversation with the iconic (and incredibly charming) Michael Nouri on episodes 149 and 151 of Hollywood Obsessed Podcast—who starred in the hilarious Christmas movie “Last Holiday”—I found myself going down a full-on holiday movie rabbit hole. It got me thinking about all the holiday comedies I’ve been obsessed with over the years—some since childhood, others I discovered later and now can’t imagine December without.

So grab a cozy blanket, plop yourself on the couch, fire up the tree lights, and maybe pour something festive. This is your invitation to take a fun, funny trip down memory lane and revisit the holiday comedies that make the season brighter, sillier, and a whole lot more joyful.

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LAST HOLIDAY (2006)

Every time I revisit this feel-good holiday favorite, I fall in love with it all over again. Queen Latifah is absolutely radiant as Georgia Byrd, a quiet department store sales associate whose life is turned upside down when she’s told she has a rare brain condition and only weeks to live. Instead of giving in to fear, Georgia does what most of us only talk about doing—she cashes in her savings and heads off on a dream European vacation to finally start living.

The cast makes this movie even more fun to watch. LL Cool J is endlessly charming as Georgia’s sweet and supportive love interest, while Timothy Hutton plays the smug retail boss you love to hate. Giancarlo Esposito is terrific as a U.S. Senator who becomes one of Georgia’s biggest allies, and Alicia Witt brings just the right amount of sparkle as Hutton’s ambitious assistant. Gérard Depardieu is unforgettable as a legendary chef Georgia idolizes, and Michael Nouri adds warmth and sophistication as a visiting Congressman drawn to Georgia’s honesty and confidence.

Last Holiday is one of those movies we’re obsessed with because it gives us everything we want this time of year—big laughs, cozy escapism, glamorous winter scenery, and a genuinely moving reminder to stop playing it safe. It’s the kind of holiday movie that makes you want to book the trip, say the thing you’ve been holding back, eat the dessert, and enjoy the moment while you can.

Funny, touching, and endlessly rewatchable, Last Holiday reminds us that life—and the holidays—are meant to be savored. And if you want some great behind-the-scenes stories from this modern holiday classic, be sure to check out my recent conversation with Michael Nouri on Episodes 149 and 150 of the Hollywood Obsessed podcast.

Click HERE to listen now!

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A CHRISTMAS STORY (1983)

Every holiday season, this endlessly hilarious classic directed by Bob Clark feels just as irresistible as ever. Set in December 1940, “A Christmas Story” follows young Ralphie Parker and his family through the wonderfully chaotic lead-up to Christmas in small-town Indiana. Based on Jean Shepherd’s semi-autobiographical book “In God We Trust: All Others Pay Cash,” the film perfectly captures that laser-focused childhood obsession with Christmas—mixed with nostalgia, humor, and just the right amount of chaos.

Peter Billingsley is unforgettable as 9-year-old Ralphie, whose one Christmas wish is the legendary Red Ryder Carbine Action 200-shot Range Model air rifle—a dream repeatedly crushed by the immortal warning, “You’ll shoot your eye out, kid!” Melinda Dillon shines as Ralphie’s warm, patient mother, while Darren McGavin steals scenes as “The Old Man,” delivering some of the most quotable moments in holiday movie history.

This is one of those holiday comedies we’re obsessed with because it feels so universal. Anyone who’s ever wanted that one perfect gift—or lived through the excitement, frustration, and anticipation of Christmas as a kid—will see themselves in this movie. And thanks to the now-iconic “24 Hours of A Christmas Story” marathon, it’s basically become a holiday institution.

Funny, nostalgic, and endlessly rewatchable, “A Christmas Story” is one of those movies you can drop into at any point and instantly feel like it’s Christmas.

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THE FAMILY STONE (2005)

From the very first time I watched this modern holiday favorite, I knew it was one I’d come back to every Christmas. “The Family Stone“ somehow manages to be cozy and sharp, funny and emotional, all at once—basically everything a real family holiday gathering tends to be. And honestly, any excuse to revisit Diane Keaton in a Christmas movie feels especially right.

The cast is stacked and perfectly chosen—Diane Keaton, Craig T. Nelson, Claire Danes, Rachel McAdams, Dermot Mulroney, Sarah Jessica Parker, and Luke Wilson—and every performance feels messy, lived-in, and real. Written and directed by Thomas Bezucha, the film centers on the Stone family’s Christmas in a small New England town, which quickly goes off the rails when Everett brings home his tightly wound girlfriend Meredith, planning to propose. Her awkward arrival sets off a chain reaction of misunderstandings, hurt feelings, unexpected connections, and emotional curveballs.

We’re obsessed with “The Family Stone” because even when the story leans a little dramatic, the emotions always feel honest. It understands that holidays can be uncomfortable, loving, painful, funny, and healing—all at the same time. If you like your Christmas movies with big laughs, messy family dynamics, and the guarantee you’ll need tissues by the end, this one is still a must-watch. And Diane Keaton? As radiant and unforgettable as ever.

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ELF (2003)

The mere sight of Will Ferrell strutting around in green tights and a pointy hat is enough to send me into uncontrollable laughter. From the very first frame, “Elf” announces itself as a modern Christmas classic, and with an outrageously talented supporting cast—James Caan, Zooey Deschanel, Mary Steenburgen, Ed Asner, and Bob Newhart—it’s no wonder this film has become an annual holiday staple.

Ferrell plays Buddy the Elf, a human raised at the North Pole who discovers his true origins and journeys to New York City to find his biological father. The movie is packed with endlessly quotable moments, but Bob Newhart’s turn as Papa Elf—Buddy’s adoptive father and the film’s narrator—is pure comedic gold. He brings warmth, wit, and impeccable timing to every scene.

And then there’s the legendary showdown with Peter Dinklage’s tightly wound children’s book author, whom Buddy repeatedly and innocently refers to as an elf—a sequence that still leaves me crying with laughter no matter how many times I’ve seen it. If “Elf” doesn’t make you feel merry, bright, and downright giddy, I’m afraid there’s only one conclusion: you’re officially a Scrooge.

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HOME ALONE (1990)

I know there are technically sequels, but let’s be honest—nothing compares to the original. Directed by Chris Columbus and written and produced by the great John Hughes, “Home Alone” is a slam-dunk holiday comedy that has earned its place as a forever Christmas classic, destined to be watched and rewatched for decades.

The film stars child star extraordinaire Macaulay Culkin as Kevin McCallister, an eight-year-old accidentally left behind when his family jets off to Paris for Christmas. What follows is suburban Chicago chaos as Kevin is forced to defend his home from two would-be burglars—the hilariously inept Wet Bandits—played to perfection by Joe Pesci and Daniel Stern. If Kevin’s elaborate booby traps don’t send you into fits of laughter, your funny bone may need professional attention. The stellar supporting cast includes John Heard and the always-brilliant Catherine O’Hara.

Kevin’s ingenious defense of his home is exactly why we love this movie, made all the sweeter by his heartfelt reunion with his family on Christmas Day. Over the years, “Home Alone” has become synonymous with the season, celebrated for its endlessly quotable lines, outrageous traps, and unforgettable hero. This holiday treat is guaranteed to keep you warm, fuzzy, and laughing through those long winter nights.

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PLANES, TRAINS AND AUTOMOBILES (1987)

There aren’t that many classic Thanksgiving comedy movies, which is exactly what makes this one so special. Written, produced, and directed by John Hughes, “Planes, Trains and Automobiles” is a bona fide holiday classic, anchored by the unbeatable pairing of Steve Martin and John Candy. The film follows Neal Page, an uptight marketing executive, and Del Griffith, a relentlessly cheerful (and endlessly irritating) salesman who are thrown together when Neal’s flight is diverted. What follows is a three-day odyssey of travel disasters as the unlikely duo attempts to make it to Chicago in time for Thanksgiving dinner.

This brilliantly funny road-trip comedy is ultimately about the importance of connection, kindness, and family—especially during the holidays. And let’s be real: there’s no funnier on-screen duo than Martin and Candy at the peak of their powers. From the immortal “THOSE AREN’T PILLOWS!” moment to Edie McClurg’s beyond-hilarious scene as the unflappable car rental agent on the receiving end of Neal’s legendary airport meltdown, the laughs are nonstop.

But beneath all the comedy is genuine heart, which is what elevates “Planes, Trains and Automobiles” from hilarious farce to timeless holiday favorite. It’s the rare Thanksgiving film that reminds us—through chaos, frustration, and plenty of laughs—that getting home, and who we share the journey with, is what really matters.

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THE HOLDOVERS (2023)

This fairly new holiday comedy completely won our hearts when it premiered in 2023. Set in 1970, “The Holdovers” tells a quietly funny and deeply touching story about a gruff classics teacher at a New England boarding school who’s stuck chaperoning a small group of students with nowhere to go during Christmas break.

The film stars Paul Giamatti as the funny-but-formidable teacher, Da’Vine Joy Randolph as the school’s cafeteria manager and grieving mother who stays behind for the holidays, and Dominic Sessa as one of the students “held over” on campus. It earned widespread critical acclaim, was named a Top 10 Film of 2023 by both the National Board of Review and the American Film Institute, and received five Academy Award nominations—including Best Picture. (And yes—Randolph won Best Supporting Actress. Yippee!)

What makes “The Holdovers” so special is its big heart. With its warm, retro look and nostalgic tone, the film tells a deeply human story about lonely, imperfect people finding unexpected connection during the most emotional time of the year. If you haven’t seen it yet, trust us—it’s destined to become a permanent fixture on your holiday watchlist.

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NATIONAL LAMPOON’S CHRISTMAS VACATION (1989)

If you’re the type who aims for the perfect Christmas every year, this holiday classic is absolutely about you. The third film in the “National Lampoon’s Vacation” franchise follows Clark Griswold (Chevy Chase), his wife Ellen (Beverly D’Angelo), and their kids as they host the entire family for Christmas in their Chicago-area home—with predictably chaotic results.

Watching Clark slowly (and hilariously) unravel as the holidays spiral out of control is endlessly relatable. From battling endless strands of Christmas lights to obsessing over the ideal family celebration, his festive meltdown feels all too familiar. The film is also packed with unforgettable supporting performances, including Julia Louis-Dreyfus as the long-suffering yuppie neighbor Margo Chester and Nicholas Guest as her equally tormented husband, Todd.

At its core, “Christmas Vacation” perfectly captures the madness of the season—family drama, financial stress (that infamous bonus!), and increasingly ridiculous mishaps, including rogue squirrels and holiday décor disasters. Beneath the over-the-top comedy is real heart, making this a guaranteed laugh and a reminder that no Christmas is ever truly perfect—and that’s exactly what makes it fun.

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SCROOGED (1988)

This wildly entertaining and unapologetically modern reimagining of Charles Dickens’ “A Christmas Carol” proves that the story truly is timeless. Directed by Richard Donner, this Christmas fantasy black comedy stars comic genius Bill Murray as Frank Cross, a cynical, self-absorbed television executive who is deep in production on a live broadcast of “A Christmas Carol”—when his own Christmas Eve takes a supernatural turn.

As tradition dictates, Frank is visited by a series of ghosts determined to help him rediscover his long-lost holiday spirit. The film boasts an incredible supporting cast, including Karen Allen, John Forsythe, Bobcat Goldthwait, Carol Kane, Robert Mitchum, John Glover (who has also been one of my fabulous guests on Hollywood Obsessed Podcast), Michael J. Pollard, and Alfre Woodard, each adding to the film’s chaotic, irreverent charm.

We still love “Scrooged” for its perfect balance of biting satire and heartfelt redemption. Bill Murray’s cynical-yet-undeniably charming anti-hero anchors the film, while Carol Kane’s unhinged (and unforgettable) Ghost of Christmas Present delivers some of the movie’s biggest laughs. Its sharp commentary on holiday commercialism feels even more relevant today, and beneath its dark, edgy humor lies a genuinely moving message about compassion, generosity, and second chances.

If you needed a reminder, here it is: “Scrooged” remains a beloved alternative Christmas classic—and odds are, now that we’ve mentioned it, you’ll be watching it tonight and laughing your ass off.

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NOTHING LIKE THE HOLIDAYS (2008)

Directed by Alfredo De Villa, this modern holiday gem centers on a close-knit Puerto Rican family living in Chicago’s Humboldt Park neighborhood as they face what may be their last Christmas together under the same roof. As with any family gathering, especially during the holidays, unresolved tensions and long-buried emotions begin to surface.

The film features a fantastic, predominantly Latino ensemble cast—refreshing and long overdue representation on screen—including Luis Guzmán, John Leguizamo, Alfred Molina, Freddy Rodriguez, Melonie Diaz, Vanessa Ferlito, Jay Hernandez, and Elizabeth Peña. Debra Messing shines as Mauricio’s Jewish wife, Sarah, adding another layer of cultural contrast and emotional complexity to the story.

We continue to return to “Nothing Like the Holidays” for its authentic portrayal of family dynamics, its strong ensemble performances, and its heartfelt message about love, forgiveness, and reconciliation. Funny, tender, and emotionally honest, this holiday dramedy explores identity, cultural clashes, and the beautifully messy reality of family life. If you haven’t seen it yet, do yourself a favor and add this warm, soulful holiday film to your seasonal watchlist. Feliz Navidad!

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MARCH OF THE WOODEN SOLDIERS (1934)

This hilarious Laurel and Hardy holiday classic remains one of my all-time favorite childhood holiday films. I vividly remember watching this beloved Thanksgiving Day staple every year on WPIX (Channel 11) in New York City—a tradition that felt just as important as the holiday itself.

Based on Victor Herbert’s popular 1903 operetta “Babes in Toyland,” the film was produced by comedy legend Hal Roach and is set entirely in the magical land of Toyland. The story unfolds among Mother Goose (Virginia Karns) and a host of familiar fairy-tale and nursery-rhyme characters, creating a whimsical fantasy world that feels tailor-made for the holiday season. The film features five complete musical numbers, including the opening “Toyland,” “Never Mind Bo-Peep,” “Castle in Spain,” “Go to Sleep (Slumber Deep),” and the unforgettable instrumental finale, “March of the Toys.” Every minute of it is pure joy.

Audiences continue to adore “March of the Wooden Soldiers” for its timeless charm, Stan Laurel and Oliver Hardy’s iconic comedy, impressive early special effects, and its heartwarming message that good ultimately triumphs over evil. It’s a comforting, magical escape that feels especially perfect between Thanksgiving and Christmas.

If you haven’t revisited it in a while, do yourself a favor and stream it today. I promise—it will transport you straight back to your childhood.

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A CHARLIE BROWN CHRISTMAS (1965)

No Christmas season goes by without watching this animated classic at least once (twice if I’m lucky). Ever since I was a kid, I’ve loved all things Peanuts, but “A Charlie Brown Christmas” has always been my favorite of them all.

People still love this holiday TV special for all the right reasons: the mellow jazz music, the simple animation, and its honest take on holiday commercialism. It has a quiet, meaningful message about finding the true spirit of Christmas—one that really hits if you’ve ever felt stressed, anxious, or a little out of place during the holidays. And honestly, that’s most of us.

The humor is subtle but always lands. The deadpan dialogue still makes me laugh (especially Lucy calling Christmas a “big commercial racket”), and Snoopy’s antics never get old—whether he’s dancing, skating, or pretending he’s a WWI flying ace. And no matter how many times I’ve seen it, Charlie Brown’s sad little tree losing all its needles somehow makes me laugh and feel warm at the same time.

Bottom line: if you only watch one holiday comedy this season, make it “A Charlie Brown Christmas.”

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From snow-covered suburbs and leg lamp–lit living rooms to airport meltdowns, wet bandits, and candy-cane–fueled elves, holiday comedies are the gift that keeps on giving. Whether you’re laughing along with “Home Alone” and “A Christmas Story,” getting misty-eyed with “The Family Stone” and “The Holdovers,” or quoting “Planes, Trains & Automobiles,” “Christmas Vacation,” and “Scrooged” for the hundredth time, these movies have a magical way of wrapping humor, heart, and nostalgia into one perfectly bingeable package. Toss in the timeless charm of “A Charlie Brown Christmas,” the delightfully nostalgic “March of the Wooden Soldiers,” and the soulful warmth of “Nothing Like the Holidays,” and you’ve got yourself a full-on festive feast.

So grab the popcorn, spike the eggnog (or don’t—we don’t judge), and settle in with one—or several—of our holiday comedy obsessions. From our home to yours, we wish you a very Merry Christmas and the happiest of Holidays. Now press play and let the holiday silliness begin!

To hear more fun stories about filming “Last Holiday” with Queen Latifah tune in to my in-depth, funny, entertaining, and absolutely fascinating conversation with the legendary leading man, Michael Nouri. He shares incredible memories, behind-the-scenes gems, and jaw-dropping insights that every “Last Holiday” fan will enjoy.

Listen to the full interview on the Hollywood Obsessed Podcast click below.

Episode 149 - HERE

Episode 150 - HERE

Some facts in this post were sourced from IMDb and Wikipedia.