21 Underrated Holiday Films to Watch This Christmas Season

by the light of the silvery moon
Image Credit: Warner Bros.

Every Holiday Season, there are those Christmas movie staples we love to watch, from Elf to It's A Wonderful Life. And with every coming year, more films are made that we add to our list of favorites. In this list, there are 21 of those types of films, many of which are lesser known or even sometimes maligned. But over the years, some were underrated in their own time and have been forgotten or even unfairly disregarded.

While film is subjective, some movies deserve a first, or in some cases, a second watch. After all, the Holidays are a time for second chances and embracing others. In that spirit, there is something for everyone here, from classic dramas to romances to family comedies. For even more underappreciated Christmas films, check out last year's list of The Most Underrated Christmas Movies to Watch this Holiday Season. Meanwhile, here is a list of worthwhile festive flicks to watch this Christmas.

Christmas With the Kranks (2004)

christmas with the kranks
Image Credit: Revolution Studios

In this equally hilarious and heartfelt film, Luther and Nora Krank are legendary in their Christmas spirit. Every year in their neighborhood, the couple goes all out decorating and through a big Holiday party. When their daughter Blair says she's going to Peru instead of being home for Christmas, they decide to skip Christmas and go on a cruise instead. But when she says at the last minute that she's coming home, the race is on to create a perfect Christmas.

With plenty of madcap and slapstick humor in capable actors such as Tim Allen, Jamie Lee Curtis, and Dan Aykroyd, Christmas With the Kranks is one of the funniest holiday films. But with the genuine heartfelt moments, we see a real sense of community, friendship, kindness, and generosity, which is what the season is truly about.

(Available on DVD, to stream on FreeVee, and rent VOD)

Deck the Halls (2006)

deck the halls
Image Credit: Twentieth Century Fox

This holiday comedy not only features a stellar ensemble cast that includes Matthew Broderick, Danny DeVito, Kristin Davis, and Kristin Chenoweth but also an ample amount of laughs, zany antics, and heart. In the film, two neighbors become bitter rivals during the holiday season: Steve Finch, the man who loves traditions with his family and classy décor, and Buddy Hall, a bit of a con artist with ostentatious taste.

The rivalry starts simply but escalates when Buddy wants his Christmas lights to be seen from space. And soon, their fighting begins to affect what should be a happy time with the families. The comedy may sometimes feel over-the-top but is grounded by the top-notch and hilarious cast. In the end, the themes of community and forgiveness help make this one a charmer.

(Available on DVD, to stream on Spectrum and STARZ, and rent VOD)

The Family Stone (2005)

the family stone
Image Credit: Twentieth Century Fox

Family get-togethers can be stressful, especially during the Holiday season when the pressure is on to make it perfect and to welcome potential new family members. Such is the case in this film, which perfectly blends tender and serious drama with relatable humor. In the story, Everett Stone brings his girlfriend Meredith home for Christmas with the intent of proposing to her. But almost instantly, there are significant clashes between uptight and conservative Meredith and the liberal and unconventional Stone family.

Arguments, disagreements, and rising tensions abound with secrets and romantic entanglements, which complicates this holiday weekend. And yet, despite their differences, we see that common ground, compassion, and warmth are possible with a touch of forgiveness, understanding, and humility. Many will likely relate to this film, which is bolstered by its grounded and poignant themes. With a superb ensemble cast that includes Dermot Mulroney, Sarah Jessica Parker, Diana Keaton, Rachel McAdams, Claire Danes, Luke Wilson, and Craig T. Nelson, The Family Stone should be a Holiday staple.

(Available on DVD, to stream on Pop, Spectrum, and STARZ, and rent VOD)

The Family Man (2000)

the family man
Image Credit: Universal Studios

In the long and varied career of Nicholas Cage, The Family Man represents one of his most underrated films and performances. The story begins with a young couple named Jack and Kate (Cage and Téa Leoni) saying goodbye at the airport. Jack is leaving for a job, but Kate doesn't want him to go and for them to elope instead. Jack boards the plane, and many years later, he is a single, slick, high-paid executive.

But Jack still has a good heart, and when he stops a robbery, an angel (Don Cheadle) gives him a glimpse of what married life with Kate would be like. Although Jack resists this married life, with two young kids, a house in the suburbs, and a humble job as a tire salesman, he soon learns to embrace it. But despite all this, he still has much to learn about what matters in life.

This Capra-esque and heartfelt drama is well-acted and thoughtful. Moreover, moments equally funny and heartwarming shed light on the power of our choices. This film set during Christmas may feature a familiar scenario, but it is one of the finest Holiday fantasies.

(Available on DVD, to stream on Peacock, Sprectrum, and Philo, and rent VOD)

Funny Farm (1988)

funny farm
Image Credit: Warner Brothers

In this silly and sweet comedy, Andy and Elizabeth Farmer decide to move from the city and buy a farm in a small and picturesque town in Vermont. Andy was expecting a quiet life where he could finally write his novel, but instead, there is nothing but trouble from the start, from crazy neighbors to a body buried in the backyard. And while Elizabeth fares better and finds the inspiration she harnesses into a children's book, this new life is still not what they hoped.

At Christmas, they decide to try to sell their farm. And it becomes a challenge to make this small hamlet appear quaint and idyllic, straight out of a Norman Rockwell painting. And in the process, they see what life could be. With the combination of wackiness and sweetness, Funny Farm is about finding the best in the people and life, no matter how outlandish it may seem. It's a delight.

(Available on DVD and to rent VOD)

I'll Be Seeing You (1944)

Ill be seeing you 1
Image Credit: United Artists and Selznick International Pictures

This tender and poignant classic drama stars Ginger Rogers and Joseph Cotton as lonely souls who find understanding and love during the Holidays. Rogers plays a woman on a furlough from prison serving a sentence for accidental manslaughter, allowed to visit her family for Christmas. Cotton plays a soldier whose wounds go beyond the physical. What was once called “shell shock,” we now call PTSD, and plagues this brave man in ways few can understand. The two meet on the train, and their mutual loneliness and sense of isolation bring them together in a meaningful way.

More serious Holiday fare, I'll Be Seeing You showcases Christmas in a different light and depicts individuals that life has cast a shadow on, unable to see the light at the end of the tunnel. Overall the film is thoughtful, beautiful, and hopeful, mirroring the joy and love the Holidays can inspire.

(Available on DVD and to stream on RetroReels)

It Happened On 5th Avenue (1947)

it happened on 5th avenue
Image Credit: Roy Del Ruth Productions and Allied Artists

A film that gets lost in the shuffle and rarely remembered is a touching story rife with what the Holiday season is truly about. Every winter, a homeless man named McKeever relocates into the mansion of one of the wealthiest men in the country, Michael J. O'Connor, knowing he always leaves town for Christmas. This year, Mr. Mckeever invites a down-on-his-luck soldier to join him in this empty home. Soon, the mansion becomes a place of refuge for more soldiers, their wives, an heiress, and unbeknownst to them all, O'Conner himself.

This charming black-and-white film demonstrates how a story can be engaging and moving yet simple in its premise. The holidays and meant to be a time of forgiveness, family, and generosity. Sometimes that family and sense of togetherness can come from the most unexpected places and a group of strangers. And these individuals discover that family is not only defined by blood. It Happened on 5th Avenue is a profound look at life's most resonant truths, seen through a Christmas lens.

(Available on DVD, to stream on HBO Max and RetroReels, and rent VOD)

Lady and the Tramp (1955)

lady and the tramp
Image Credit: Walt Disney Pictures

A vastly underrated classic Disney animated film, Lady and the Tramp, is visually gorgeous. It features a heartfelt story about a dog named Lady, her sweet owners, faithful friends, and the Tramp who wins her heart. Inspired by the story of Walt Disney, who gave his wife Lillian a puppy in a hatbox one Christmas, we see Darling open her husband, Jim Dear's, present to his wife on Christmas morning. They name the sweet cocker spaniel puppy Lady, and as she grows, we see how special dogs and their owners are to each other.

Beginning and ending at Christmas, the story in between is a mix of happy times and times of confusion, fear, and danger for Lady and her friends. Bookending the film with snowy, peaceful, and happy Christmas mornings, we see how dogs are members of our families. And sometimes the best gifts are the unexpected ones.

(Available on DVD, to stream on Disney+, and rent VOD)

Last Christmas (2019)

last christmas 1
Image Credit: Universal Studios and Jonathan Prime

A heartfelt, genuine and profound film, Last Christmas may seem like the average Christmas romantic comedy on the surface. And while the movie features humor and romance, the film's heart goes much deeper. Loosely inspired by the George Michael Christmas song, the story follows a young woman named Kate. She works in a year-round Christmas store but has grand aspirations of being a singer. Not taking care of her health as she should be, making poor decisions, and acting selfishly with those around her, Kate's life changes when she meets Tom. He is kind and charming, always appearing when she needs a dash of faith and inspiration.

While there are funny and romantic moments, Last Christmas is also a bittersweet drama about the strength and adversity of the human spirit. Life is a precious gift that should not be wasted. And the heart is not meant to be broken forever. With a little reminder to always look up, Last Christmas shows us that with belief in ourselves, a special light can always shine through.

(Available on DVD, to stream on Spectrum, and rent VOD)

Last Holiday (2006)

last holiday
Image Credit: Paramount Pictures

Genuinely funny and heartwarming, this vastly underrated film set during the Holidays stars Queen Latifah, LL Cool J, Timothy Hutton, and Gérard Depardieu. The story follows a woman named Georgia, a kind woman who has visions of what a possible future could be, including meeting the famous chefs she admires and marrying her handsome co-worker. After an accident leaves her with a concussion, she is devastated to learn she has a rare brain disease and only weeks to live.

After understandably expressing great grief, albeit alone, she decides to spend her last days in style. She travels to her dream destination, a glorious, remote winter ski resort where one of her favorite chefs works. She indulges for the first time and inspires those she meets to practice more kindness, honesty, integrity, and belief in themselves.

Last Holiday is delightful and heartfelt, with Latifah truly shining in a role tailor-made for her. As grim as the premise is, this film is about embracing life, love, and all its possibilities.

(Available on DVD, to stream on Amazon Prime and Paramount+, and rent VOD)

Meet John Doe (1941)

meet johnn doe
Image Credit: Warner Brothers

This classic, directed by Frank Capra and starring Gary Cooper and Barbara Stanwyck, gets less recognition than his Holiday masterpiece It's A Wonderful Life. While no one would deny that film's place in cinema history, Meet John Doe also deserves tremendous praise. The story begins with a reporter from a newly acquired newspaper trying to save her job by creating a sensation. She writes a letter meant to be sent from a man threatening to commit suicide in protest of the state of the world. She signs it “John Doe.” When the article becomes popular, they hire a man to be “John Doe,” and they embark on a lecture tour where he gives speeches that inspires millions across the country.

The film's message is about everyday people and how we must learn to love and respect our neighbors and build bridges between us. But as often is the case, we also see how corruption taints and threatens everything positive that “John Doe” inspired.

This film is engrossing and deeply moving with gripping performances from Cooper, Stanwyck, Edward Arnold, and Walter Brennan. The themes are still timely, most especially ones of integrity, community, and compassion. Capra can tap into what it means to be human in a beautifully affecting way. In the end, what Meet John Doe, which takes place at Christmas, ultimately shows is that the goodwill of the Holidays should be felt all year long.

(Available on DVD, to stream on Amazon Prime, Roku Channel, FreeVee, and Kanopy, and to rent VOD)

The Nativity Story (2005)

the nativity story
Image Credit: New Line Cinema

For the religious and spiritually-minded movie fan and those who wish to watch something about the “reason for the season,” The Nativity Story is a beautiful and well-acted ideal choice. Telling the Biblical story of the birth of Jesus Christ of Nazareth, young Mary (Keisha Castle-Hughes) is betrothed to a carpenter named Joseph (Oscar Isaac). One day, an angel visits Mary and tells her that she has been chosen to bear the son of God and that he will be the Savior of the World.

Not knowing what to believe creates a struggle between Joseph and Mary until he is visited by the same angel who reaffirms the miracle. Meanwhile, while King Herod fears the prophecy of a usurper who will dethrone him, we see Mary and Joseph take that fateful journey to Bethlehem.

Even for those who are not religious, there is something to enjoy, from the dramatic story to fine production and exceptional performances. And for religious people, The Nativity Story will surely be a moving film to watch when wanting to remember the meaning behind their celebrations. It's a touching film in every way.

(Available on DVD and to rent VOD)

Never Say Goodbye (1946)

never say goodbye
Image Credit: Warner Bros.

In this classic charmer, Errol Flynn and Eleanor Parker star as Philip and Ellen Gayley, divorced for one year and sharing custody of their young daughter Flip. Having spent six months with her father, Flip is preparing to spend the next six months with her mother, beginning with the Christmas Holiday. Flip is sad about leaving her father, and he wants his wife back, who still harbors feelings for him despite her protests.

And as she tries to get her parents back together, hilarity ensues, especially when a soldier Flip has been writing to using her mother's name enters the mix. It's light and warm-hearted with genuine moments of comedy, including an homage to a classic Marx Brothers scene with two Santas. Never Say Goodbye has an innocent charm and a mature sensibility and is a classic film that deserves more praise.

(Available on DVD and to rent VOD)

New in Town (2009)

new in town
Image Credit: Gold Circle Films and Lionsgate

This vastly underappreciated 2000s romantic comedy stars Renée Zellweger, Harry Connick Jr., and J.K. Simmons. The plot follows a savvy businesswoman from Florida whose company sends her to a small town in Minnesota to help restructure a struggling manufacturing plant. Completely out of her element, she is unprepared for the frigid temperatures and considerably clashes with the townsfolk.

But as one might expect, soon she finds common ground with the town as they all learn to embrace each other and find practical solutions to the plant's issues. Finding love with a handsome single father is the most unexpected, but her happiness is threatened when she is forced to make difficult business decisions and decide what matters.

This film has fallen by the wayside but is one of the sweetest romantic comedies of its era. The small-town charm, quirky characters, romance, and cozy feel of the Christmas season make New in Town a heartwarming wintery delight.

(Available on DVD and to rent VOD)

On Moonlight Bay & By the Light of the Silvery Moon (1951 & 1953)

by the light of the silvery moon 1
Image Credit: Warner Bros.

Doris Day and Gordon McRae star as the besotted sweethearts in these utterly charming period musicals that take place during the Holiday season. In On Moonlight Bay, the Winfield family moves to a new neighborhood after the father gets a promotion. It's not long before the oldest daughter, Marjorie, falls in love with the boy across the street, Bill, with many light-hearted misadventures and vignettes, including dance lessons, birthday parties, and Christmas carols. The film ends with a marriage proposal as Bill prepares to enter WWI, but it's a happy and hopeful conclusion.

By the Light of the Silvery Moon is just as wonderful as its predecessor and is even more of a Holiday film. The story begins at Thanksgiving. Bill has returned home from the war and is determined to be settled in his work before he and Marjorie are married. But romantic entanglements and confusion, mainly from Marjorie's precocious brother Wesley, make the siblings believe their father is involved with another woman.

With Thanksgiving and Christmas as a backdrop for this film, we are treated to sweet and comforting moments such as sleigh rides and ice skating serenades. Both On Moonlight Bay and By the Light of the Silvery Moon are like old-fashioned Christmas Currier and Ives prints come to life.

(Available on DVD and to rent VOD)

The Perfect Holiday (2007)

the perfect holiday
Image Credit: Capital Arts Entertainment

In this sweet-natured family comedy, all Nancy (Gabrielle Union) wants is a nice man to compliment her genuinely. Harried and essentially taking care of her three children alone, her ex-husband is preoccupied with his music career and rarely spends time with his children. Nancy always puts herself last, so her daughter asks a mall Santa (Morris Chestnut) to grant her mother's wish. So, as himself, he grants Nancy's wish. But things grow complicated when sparks fly, and more wishes are asked of Santa.

Often forgotten or underestimated, The Perfect Holiday is light entertainment but also very comforting, funny, and filled with genuine moments that showcase the wonders of opening your heart, whether it be with a romantic partner or child. With a dash of delightful whimsy from Queen Latifah and Terrance Howard, who provide a uniquely magical presence, The Perfect Holiday is a perfectly delightful diversion.

(Available on DVD, to stream on FreeVee, and rent VOD)

Planes, Trains, and Automobiles (1987)

planes trains and automobiles
Image Credit: Paramount Pictures

Set during the Thanksgiving holiday, this wacky, hilarious, and ultimately heartfelt film comes from writer/director John Hughes and stars the renowned Steve Martin and John Candy. All Neal Page (Martin) wants is to get home to his family for Thanksgiving but encounters trouble at every turn, from losing a cab to grounded planes. At the center of these mishaps is Del Griffith (Candy), an affably annoying man he meets who soon becomes Neal's shadow as they attempt to get home to Chicago.

No doubt, the humor of this film comes from the outlandish mishaps where every problem imaginable occurs on their arduous travels. But it requires the capable talents of Martin and Candy to ground the humor, make it believable, and eventually lead to its heartfelt conclusion. Despite all the troubles, the two men finally bond and discover genuine friendship and compassion on the road home. Without its moments of gravitas, Planes, Trains, and Automobiles would simply be an outrageous comedy. But with its tender moments of understanding between these two men, it becomes a classic comedy that, at its heart, is about family, unlikely friendships, overcoming grief, and generosity.

(Available on DVD, to stream on Paramount+ and PlutoTV, and rent VOD)

Prancer (1989)

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Image Credit: Metro-Goldwyn-Mayer Studios Inc.

A melancholy but affecting family drama, Prancer tells the story of a little girl convinced that the reindeer she comes across in the woods is one of Santa's reindeer. As she nurses the wounded deer in secret (at first), we see her hopeful optimism lessen the sadness and cynicism of those around her, from an odd and reclusive elderly woman to her older brother and harsh father.

Prancer is more serious holiday fare in line with films such as One Magic Christmas. It would be a welcome choice for children and families as it is a different type of Holiday film featuring a simple story with both childlike wonder and mature themes. It is sad but ultimately uplifting. The moody atmosphere, wintery setting, and fine cast that includes Sam Elliott and Cloris Leachman make Prancer a unique choice for the season.

(Available on DVD, to stream on HBO Max and Spectrum, and rent VOD)

Santa Claus: The Movie (1985)

santa claus the movie
Image Credit: Tri Star Pictures

Before The Santa Clause charmed audiences, this lesser-known whimsical film told the origin story of the man who would become Santa Claus. The kindly toy maker Nicholas, his wife, and their two reindeer are caught in a frigid snowstorm one evening until a miracle occurs. A group of elves discover the couple and bring them to the North Pole, knowing that these are the ones they’ve been waiting for. And soon, Nicholas becomes Santa, bringing joy to millions of children worldwide at Christmas.

The story takes a turn when an Elf named Patch (Dudley Moore), who wishes to modernize Santa's workshop, feels underappreciated and so leaves for New York City. But he becomes caught up with a greedy toymaker (John Lithgow), whose plans only include making money regardless of the safety of the children. It's up to Santa, and the two children along for the adventure, to set Christmas right again.

Fanciful, bright, and heartwarming, this is one of the most underappreciated Santa stories that deserves to be seen more often.

(Available on DVD, to stream on Hulu and Amazon Prime, and rent VOD)

Trapped In Paradise (1994)

trapped in paradise
Image Credit: Twentieth Century Fox

A film that combines comedy and heart, like many Holiday films, this one draws obvious inspiration from the classic movie We're No Angels. It is a story of three brothers who would never be compared to the three wise men. Bill is the most straight-laced but must fight the temptation to steal constantly. His brothers, Dave and Alvin, never win that fight within themselves. But after some smooth talking, they are released on parole from prison and reluctantly convince their brother to drive down to Pennsylvania to deliver a letter to a daughter of a fellow inmate. When they reach this small and trusting town, the lack of security at a bank is too tempting to resist.

When fate intervenes, and the weather prevents them from leaving, the three brothers are embraced by a family, and they soon feel complete and utter remorse and want to take back what they did.

The ensemble cast of Trapped in Paradise is fantastic, with the three brothers, played by Nicholas Cage, Jon Lovitz, and Dana Carvey, at the top of their comedic game. Moreover, the charming small town feels like something out of a postcard and provides beautiful visuals. Trapped in Paradise is about unselfish kindness, community, and second chances, all of which embody the spirit of Christmas.

(Available on DVD and to rent VOD)

We're No Angels (1955)

were no angels
Image Credit: Paramount Pictures

While the Three Wise Men brought gifts to Bethlehem, the three wise-cracking men in We're No Angels intend to do the opposite. Three escaped convicts (Humphrey Bogart, Aldo Ray, Peter Ustinov) on Devil's Island plan to rob a store of goods and wares and do away with the workers. But after overhearing their financial and personal struggles, these three men quickly become engrossed in their lives. And soon, despite insisting that they are not angelic, they abandon their plan and become unlikely saviors instead.

Although it takes place at Christmastime, this is not a traditional Holiday film. Consequently, that makes it not only underrated but deserves more attention and a slot in one's usual Holiday fare. The cast has tremendous panache and chemistry, the film is full of hearty laughs, and we see Bogart in a more light-hearted role. We're No Angels proves that Holiday films can come in very different looking packages.

(Available on DVD and to rent VOD)

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This article was produced and syndicated by Wealth of Geeks.

Marianne Paluso is a freelance writer and artist and holds a Masters Degree in English and Children’s Literature. Inspired by her favorite films, television, theme parks and all things pop culture, she especially loves Disney, classic films, fairy tales, period dramas, musicals, adventures, mysteries, and a good rom-com. She joined Wealth of Geeks in 2021, and has also contributed to The Nerd Machine, Catholic News Agency. She writes on her own website TheGirlyNerd.com, creates art that is sold on Redbubble and Etsy, and also partakes in the occasional Disneybound, cosplay, and YouTube video