‘Tis the season for nostalgia, and what better place to start than with the ’90s? The 1990s were a magical time for Holiday Films, one that brought moviegoers beloved Christmas classics from Home Alone and The Santa Clause. The decade saw cinema’s most popular stars trying their hand at the wholesome holiday genre, including big names like Michael Caine, Joe Pesci, Michael Keaton, and Tim Burton. This was when the world was first introduced to the devious antics of Macaulay Culkin’s unruly Kevin McCallister, Tim Allen’s transformation into the big man himself, and Arnold Schwarzenegger’s battle with Sinbad over a highly coveted action figure. There is so much to choose from, all of it golden, festive, and timeless.
With the holiday season right around the corner, let’s take a look at some Christmas movies the 1990s had to offer, ranking up to the best of the era. Will it be Kevin McCallister, Jack Skellington, or Santa himself? Regardless, each of these 9 entries stands as one of the best holiday films not just of the ’90s but of all time.
9
‘Jingle All the Way’ (1996)
In the 1996 action comedy Jingle All The Way, action legend Arnold Schwarzenegger is a man on a mission — a toy mission. The cinema superstar appeared as a workaholic sales representative who goes head-to-head with a fellow postal father (played by Sinbad) in a quest to purchase a highly coveted action figure on Christmas Eve.
Poking fun at the over-commercialization of the jolly holiday, this relatable blockbuster hit was inspired by real-life toy manias. In the days before online shopping, sell-out toys like Mighty Morphin Power Rangers, Furbys, Tamagotchis, and Cabbage Patch Kids would incite near riots as consumers clamored over each other for the perfect gift. It’s important to note that this film perfectly depicts the often aggressive nature of holiday shoppers while still managing moments of comedic lightness and general frivolity. Though the holiday picture failed to resonate with critics, moviegoers thoroughly enjoyed the Christmas comedy.
8
‘Jack Frost’ (1998)
Actor extraordinaire Michael Keaton led the 1998 fantasy film Jack Frost. In it, the seasoned star portrays a neglectful but kind-hearted father and rock band musician who is tragically killed in a car accident during a snowstorm, leaving his devastated wife and young son to pick up the pieces. Their world is turned upside down when he seemingly returns as, what else, but a snowman? Keaton’s eponymous character is given a second chance with the help of a magical harmonica and sets out to make things right with his beloved son.
Not to be confused with the similarly titled horror classic, this film flew under the radar for years before becoming a truly heartfelt cult classic. While it was notorious for its questionable snowman design, kind of uncanny valley by today’s standards, that many find more creepy than cheerful, its message of spending time with family while you can make it a heartfelt 90s flick. At the same time, the movie stands as a testament to the medium’s ability to navigate difficult themes some children face, such as loss of family around the holidays.
7
‘Mickey’s Once Upon a Christmas’ (1999)
Mickey’s Once Upon a Christmas features three very different festive tales featuring cherished characters like Donald Duck, Goofy, Scrooge McDuck, and Mickey himself. Kelsey Grammer narrates the charming Christmas film, with each segment taking inspiration from short stories like “The Gift of the Magi” by O. Henry and William Dean Howells’ “Christmas Every Day.” Wayne Allwine and Russi Taylor are famously known for voicing the iconic power couple of Mickey and Minnie Mouse. The voice performers became well-known for having been married during much of their tenures as the iconic Disney characters (much to the delight of audiences everywhere).
Disney’s 1999 anthology fantasy Mickey’s Once Upon a Christmas is an underrated holiday gem. The 1990s and 2000s were an era marked by the widespread distribution of new and classic Disney shorts on VHS and DVDs alike. No longer limited to playing in theaters before an upcoming film, this allowed the company to distribute its shorts to a whole new audience, one who could watch them over and over again. Pairing this with stories that mimicked yearly traditions was the next logical step, one that complemented these originals. Disney continues this trend, offering new seasonal shorts every year on streaming, but Mickey’s Once Upon a Christmas will always hold a special place in the memories of Mickey Mouse fans.
6
‘The Santa Clause’ (1994)
Tim Allen is a reluctant Saint Nick in the 1994 Christmas comedy The Santa Clause. The story follows grumpy toy sales representative Scott Calvin after he accidentally causes the real Santa to fall off his roof. Scott and his son Charlie manage to complete the monumental task of delivering the rest of Kris Kringle’s toys before sunrise, only to realize that they should’ve read the fine print. Now, the man formerly known as Scott Calvin is obligated to become Santa Claus on a more permanent basis.
This fun and festive picture was a critical and commercial hit, launching a popular and lucrative Santa Clause franchise that Christmas lovers revisit year after year. A well-received limited series titled The Santa Clauses was released on Disney+ in November 2022. This heartfelt original, however, is the one that started it all, and so it is definitely worth a watch. Here, seeing Tim Allen’s Santa transform from a cold corporate shill to a generous and jolly St. Nick, is an uplifting story that perfectly encapsulates the happiness and charity that many feel during the holidays.
5
‘Home Alone 2: Lost in New York’ (1992)
The delightfully devious Kevin McCallister was back at it again in the 1992 comedy Home Alone 2: Lost in New York. The now 10-year-old has, once again, been separated from his family during the holidays. Stuck smack in the middle of the Big Apple, he decides to treat himself to the best Manhattan has to offer. Unfortunately, the Wet Bandits are also out and about in New York City, and they’re just as eager for revenge.
Macaulay Culkin shines in all his mischievous glory as the perpetually left behind Kevin, once again using his creative mind to concoct inventions that protect him from the dishonorable thieves Harry and Marv (played by Joe Pesci and Daniel Stern). His antics while staying in a luxurious Plaza Hotel suite are the stuff of childhood dreams. Chock-full of cameos (including the now-infamous one with Trump), Home Alone 2: Lost in New York earned mixed reviews from critics and immense love from moviegoers. Now, 30 years later, the sequel has become a cherished Christmas staple, just like its predecessor.
4
‘Miracle on 34th Street’ (1994)
Sensational ’90s child actress Mara Wilson (Matilda) stars in Miracle on 34th Street as six-year-old Christmas skeptic Susan Walker, who begins to question whether old Saint Nick may actually be real after meeting a mall Santa who claims to be Kris Kringle himself. On her mission to prove that the man is, in fact, Santa Claus, Susan teams up with her mother’s lawyer boyfriend to silence any naysayers once and for all.
The stirring flick may not entirely live up to the legacy of the 1947 picture, but it remains an endearing reimagining of the timeless tale. Modernized for the day, it featured several popular actors of the time, including Richard Attenborough, Elizabeth Perkins, and Dylan McDermott, and still holds a special place in the hearts of audiences everywhere. Notably, the film captures a nostalgia of Christmas’s past to utter perfection, from the department store pageantry to the festive decorations strung throughout an idyllic New York.
3
‘The Nightmare Before Christmas’ (1993)
From the genius mind of director Henry Selick (with a story by Tim Burton) comes the critically acclaimed 1993 stop-motion musical fantasy The Nightmare Before Christmas. The Disney classic tells the thrilling tale of Halloween Town King Jack Skellington as he attempts to shake up his community’s monotonous spooky rituals by taking on a brand-new holiday — Christmas. Will the residents of Halloween Town successfully conquer the Christmas season without ruining it for everyone else in the process?
The ’90s juggernaut was lauded by both critics and audiences, with Burton earning widespread praise. This Oscar-nominated cult classic is a go-to for fans of both Christmas and Halloween, often sparking an ongoing debate about which holiday it more rightfully belongs to. Either way, this film is just perfect for the transition into the more wintry months. The songs, in particular, will have audiences singing along and getting into the holiday spirit, whether it be Halloween or Christmas. The visuals have also become iconic, with Jack Skellington and Sally forever immortalized in pop culture.
2
‘The Muppet Christmas Carol’ (1992)
The great Michael Caine is superb as the grumpy, cold-hearted miser in the 1992 musical dramedy The Muppet Christmas Carol. The Charles Dickens reboot centers on the selfish Ebenezer Scrooge as he is visited by the spirits of Christmas past, present, and future. The quirky and charming Muppets help tell the celebrated holiday story, with the characters taking on iconic roles, from Kermit the Frog as Scrooge’s loyal employee Bob Cratchit, to the cantankerous duo Statler of Waldorf as Jacob and Robert Marley.
The Muppet Christmas Carol has gone on to become a beloved fan-favorite Christmas movie that includes toe-tapping musical numbers such as “Scrooge,” “Good King Wenceslas,” and “Thankful Heart.” The farce is surprisingly faithful to the original, which is no mean feat when casting puppets in the titular roles.
Caine’s singing is downright delightful, but his acting chops are on full display as well. Caine insisted on it and was granted permission to treat the role as by the book as possible, imagining his puppet cohorts as simply fellow actors, stating, “I’m going to play this movie like I’m working with the Royal Shakespeare Company. I will never wink, I will never do anything Muppety. I am going to play Scrooge as if it is an utterly dramatic role.” Not only does this work perfectly for the crotchety Scrooge, but it also allows the antics of The Muppets to shine as true holiday celebrants.
1
‘Home Alone’ (1990)
Undeniably, the most enduring and cherished ’90s Christmas classic is Chris Columbus’ 1990 holiday spectacular Home Alone. The film features the exceptional Macaulay Culkin as rambunctious misfit Kevin McCallister, an 8-year-old boy who is mistakenly left behind by his large extended family for the holidays. After enjoying some well-deserved peace and quiet, his solitude is broken by a pair of wily burglars known only to themselves as the Wet Bandits. Joe Pesci and Daniel Stern are absolutely hilarious as bumbling thieves Harry and Marv, who target the homes of people on holiday vacations. The criminals bite off more than they can chew, however, when they decide to hit the McCallister house. They’re put through the wringer, falling victim to Kevin’s increasingly harmful inventions.
Not Just One of the Best Christmas Movies of the ’90s but the Best of All Time
Home Alone made Culkin a bona fide child superstar and went on to become the highest-grossing live-action comedy for over two decades, earning $476.7 million worldwide. Touted as one of the best Christmas films of all time, its touching and hilarious descriptions of imperfect families make this a beloved flick for multiple generations. While it did spawn a series of sequels, this film is without a doubt the best of them and one which many have included as a must-watch in their annual rotation.