By Neia Balao
9:55am PST, Dec 4, 2021
"The Holiday" on Hulu & Prime Video
The holiday season is well underway, and one aspect of it we can't help but love? Having the ability to cozy up on the couch and turn on a quality film! Join Wonderwall.com as we take a look at the best holiday movies from the '90s and '00s and where to stream them, starting with this romantic tale. Who else wishes a home exchange website was a real thing?! 2006's "The Holiday" stars Cameron Diaz as Amanda Woods, a successful Los Angeles-based movie trailer producer, and Kate Winslet as Iris Simpkins, a writer for London's Daily Telegraph. Following a brutal breakup and a realization that the guy she's been pining over will never actually commit to her, Amanda and Iris meet online and decide to swap homes for a week. Of course, while in each other's respective cities, the women begin to fall in love — Amanda with Iris's brother, Graham (Jude Law), and Iris with Amanda's composer, Miles (Jack Black). In need of some uber-romantic, cross-ocean holiday viewing? Look no further.
Keep reading for more great holiday flicks and where to stream them…
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What is it called when you meet someone by happenstance and decide to let fate determine whether or not you end up together? Oh, right — serendipity! Set in New York City, 2001's "Serendipity" starring John Cusack and Kate Beckinsale tells the story of a man and woman, who, after meeting at a restaurant, decide to write their respective contact info on a $5 bill and inside a hardcover book. Should they be meant for one another, they'll eventually get ahold of each other's numbers. Sounds pretty simple, right? Well, considering they live on opposite ends of the world and are romantically involved with other people… not exactly! Fall in love with "Serendipity" on Netflix, Pluto TV or YouTube.
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"Love Actually" on YouTube, Apple TV & Prime Video
What more can we say about 2003's "Love Actually" other than that it's basically one of the most beloved holiday films of all time? Written and directed by Richard Curtis, the romantic comedy explores the intertwined lives of various Londoners as Christmas Day approaches. One particular storyline we can't help but get incredibly invested in? Sam's (Thomas Sangster) massive crush on his American classmate, Joanna (Olivia Olson), and the lengths he goes to to get her attention. From excitement and hope to grief and heartbreak, the film explores the various emotions so many feel during the holidays.
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"Elf" on HBO Max, Hulu & Starz
There are few films quite as wholesome as 2003's "Elf." Will Ferrell stars as the titular human elf Buddy, who leaves the North Pole in an effort to reconnect with the father who doesn't know he exists, Walter, a big-time businessman in New York City. Upon arriving in the Big Apple, Buddy soon realizes that reality does not live up to his expectations — namely that his biological father isn't as welcoming as he anticipated and the holiday spirit seems to be lacking in those around him. Thankfully, with the help of his love interest Jovie (Zooey Deschanel) and young half-brother Michael (Daniel Tay), Buddy takes it upon himself to reignite the magic of Christmas as best he can.
"Home Alone" on Disney+, YouTube & Prime Video
What do you do when your parents accidentally leave you behind while they go on vacation for the holidays? You protect your home from a couple of criminals who are trying to break into it, obviously. In 1990's "Home Alone," Macaulay Culkin stars as resourceful 8-year-old Kevin McCallister, who takes on the Wet Bandits (Joe Pesci and Daniel Stern) as they attempt to break into his family's house during the holidays.
"Home Alone 2: Lost in New York" on Disney+, YouTube, Apple TV & Prime Video
You'd think after the first time, the McCallisters would know better, right? Wrong. In 1992's "Home Alone 2," a now 10-year-old Kevin McCallister finds himself alone in New York City when he accidentally follows a man, whom he thought was his father, onto the wrong plane. While in Miami, his family frantically searches for a way to reunite with him. Meanwhile, Kevin seems to be living it up at the Plaza Hotel (thanks to his dad's credit card!) — but his fun is cut short when he encounters a couple of familiar foes: the Wet Bandits.
"How the Grinch Stole Christmas" on YouTube, Apple TV & Google Play
In 2000's "The Grinch," the titular villain (played by Jim Carrey) has long lived a despicable life of isolation just beyond the parameters of Whoville. However, if there's one person to change his mind about the town's inhabitants and the holiday as a whole, it's Cindy Lou (Taylor Momsen)! This Christmas classic tells the story of the Grinch's unlikely but incredibly wholesome friendship with the 6-year-old girl, who manages to thaw his ice-cold heart.
"The Family Stone" on Tubi, YouTube & Apple TV
With an ensemble cast that includes Diane Keaton, Sarah Jessica Parker and Rachel McAdams, 2005's "The Family Stone" explores the chaos and complexities of bringing together a large family over the holidays. When the eldest son of the Stone family, Everett (Dermot Mulroney), invites his rigid girlfriend, Meredith (Sarah Jessica Parker), home for the holidays with the intention of proposing to her, she brings her younger sister along (Claire Danes) for backup, which causes even more tension in the household. It wouldn't be the holidays without heightened emotions and clashing personalities, right?
"Perfect Holiday" on Hulu, YouTube & Apple TV
A Christmas-themed romantic comedy starring Gabrielle Union? Count us in! In 2007's "Perfect Holiday," Gabrielle stars as Nancy, a divorced mom of three who struggles to get into the holiday spirit. After overhearing her mom wish for a man to compliment her, Nancy's daughter Emily (Khail Bryant) reaches out to Benjamin (Morris Chestnut), a mall Santa Claus, to help fulfill her mom's request. Of course, what starts off as a simple compliment soon turns into something more. Fun fact: This holiday flick was both produced and narrated by the one and only Queen Latifah!
"The Nightmare Before Christmas" on Disney+, YouTube & Apple TV
Tim Burton's 2007 film "The Nightmare Before Christmas" tells the story of the King of Halloween Town, Jack Skellington, who, after entering Christmas Town, becomes infatuated with all things pertaining to the holiday. When his townspeople fail to believe him, Jack thinks up a diabolical plan: to take over Christmas and steal Santa Claus for Halloween Town.
"Just Friends" on Netflix, YouTube & Apple TV
Talk about a redemption story! 2005's "Just Friends" stars Ryan Reynolds as Chris Brander, a formerly unpopular and unconventionally attractive teenager whose high school experience revolved around pining over his best friend, Jamie Palamino (Amy Smart) — who friend-zoned him back in the day. Ten years later, Chris is now a successful record executive who's romantically involved with vapid pop star Samantha James (Anna Faris). It seems some things haven't changed, though, because Chris is still totally crushing on Jamie! When his Parisian holiday plans don't work out, Chris makes the decision to return to his hometown over the holidays where he works to win her affections.
"Miracle on 34th Street" on Hulu, Sling TV & YouTube
1994's remake of "Miracle on 34th Street" stars Mara Wilson as 6-year-old Susan Walker, a little girl who, under the influence of mother Dorey, is skeptical of Santa Claus's existence. However, when Dorey hires a man who claims to be Kris Kringle to take photos with children at Macy's, she and Susan slowly but surely become believers and come to his defense when people doubt the validity of his identity.
"Mean Girls" on Paramount+, YouTube & Prime Video
2004's "Mean Girls," which was written by Tina Fey, spans a full school year and isn't a traditional holiday film, but it does have one of the greatest holiday-themed scenes of all time — The Plastics' choreographed performance of "Jingle Bell Rock" during the talent show. Shout-out to Ariana Grande for recreating this iconic scene in her 2018 music video for "thank u, next."
"The Polar Express" on HBO Max, Hulu & Prime Video
In need of an entirely wholesome and beautifully animated watch? We present to you 2004's "The Polar Express." Directed by Robert Zemeckis (who famously directed the "Back to the Future" trilogy), the film chronicles the experiences of a young boy who boards a train headed to the North Pole so he can meet Santa Claus. While on his journey, he meets various people who leave a lasting impact on his life. Tom Hanks voices a series of characters in the Academy Award-nominated film including Hero Boy, Scrooge and Santa.
"I'll Be Home for Christmas" on Disney+, YouTube & Prime Video
Who didn't love Jonathan Taylor Thomas in the '90s?! In 1998's "I'll Be Home for Christmas," the "Home Improvement" heartthrob took on the starring role of Jake, a university student who's bribed to spend the holidays with his estranged dad (Gary Cole) in exchange for a Porsche. The seemingly foolproof plan is ruined, however, when Jake is abandoned in a desert (thanks to a group of bullies) and must figure out a way home as Christmas looms.
"The Family Man" on YouTube, Apple TV & Prime Video
Loosely inspired by the classic holiday flick "It's A Wonderful Life," 2000's "The Family Man" explores the "what ifs" in life. Nicolas Cage stars as Jack Campbell, a successful and single New York City businessman who finds himself imagining what life could've been had he decided to stay with his college girlfriend, Kate, rather than leave for a year-long internship in London. Magically, he is given a glimpse into that life and begins to realize that he'd rather that be his reality.
"Four Christmases" on HBO Max, Hulu & YouTube
In 2008's "Four Christmases," Reese Witherspoon and Vince Vaughn star as a Kate and Brad, a couple who decide to spend the holidays in Fiji. Their vacation, however, is ruined when a weather issue forces them to cancel their plans — and they instead get pressured into visiting all four of their respective divorced parents on Christmas Day. The comedy also includes appearances from stars like Kristin Chenoweth, Tim McGraw, Mary Steenburgen and Jon Favreau.
"Eight Crazy Nights" on YouTube, Sling TV & Prime Video
Co-written by and starring Adam Sandler, the 2002 adult animated-musical holiday flick "Eight Crazy Nights" — which focuses on Jewish characters around Hanukkah — follows a man's shot at redemption. Adam voices Davey Stone, a 30-something whose hard-partying ways have long gotten him into trouble. In an effort to give Davey a final chance to change, a judge orders him to become the assistant referee to a youth basketball league over the holiday season. What starts off as a seemingly painless gig soon takes a turn and becomes far more difficult when Davey meets the off-putting, elf-resembling main referee, Whitey Duvall (also voiced by Adam).
"Jingle All the Way" on Hulu, YouTube & Prime Video
Ah, a cautionary tale of the importance of buying your Christmas gifts well in advance. 1996's "Jingle All the Way" stars Arnold Schwarzenegger as workaholic Howard Langston, who, after failing to purchase the most coveted toy of the season — Turbo Man — for his son, must frantically track it down on Christmas Eve. While hunting down Turbo Man, Howard meets postal worker Myron Larabee (Sinbad), a rival dad who's also in hot pursuit of the same toy.
"The Muppet Christmas Carol" on Disney+, YouTube & Prime Video
Based on Charles Dickens' 1843 novella, 1992's "The Muppet Christmas Carol" focuses on the detached and unsympathetic Scrooge (Michael Caine), who begins to receive visits from spirits who are eager to help him recognize and maybe even correct some of his wrongdoings — but it may be too late for any long-lasting change. Kermit the Frog plays Bob Cratchit, Scrooge's ill-treated clerk.
"Deck the Halls" on HBO Max, Hulu & Apple TV
2006's "Deck the Halls" stars Kristin Chenoweth and Danny DeVito as Tia and Buddy Hall, and Kristin Davis and Matthew Broderick as rivals Kelly and Steve Finch, who work incessantly to outdo each other when it comes to decorating their homes for the holidays. Despite starting off as cordial neighbors, Steve becomes jealous when Buddy's house appears to be better and more excessively decorated than his. What ensues? A bit of friendly competition!
"Jack Frost" on HBO Max, YouTube & Prime Video
What if you were given the opportunity to right your wrongs? 1998's "Jack Frost" explores this magical possibility. Michael Keaton stars as the titular character, a man whose dream of becoming a successful musician had long taken precedence over spending time with his wife (Kelly Preston) and son (Joseph Cross). However, when Jack tragically dies in a car crash, he's miraculously brought back to life as a snowman! Now, with a second chance to spend time with his family, Jack finds a way to reconnect with the son he loved and lost.
"Christmas with the Kranks" on Hulu, Starz & Prime Video
2004's "Christmas with the Kranks" stars Tim Allen and Jamie Lee Curtis as a couple who excitedly plan to hop on a cruise to the Caribbean instead of staying home for the holidays. The only issue? Their holiday-loving neighbors (played by Dan Aykroyd and M. Emmet Walsh) want desperately to prevent the vacation from happening because of their desire to win their neighborhood's best decorated street competition. So much for taking a break from all that holiday chaos!
"The Santa Clause" on Disney+, YouTube & Prime Video
What happens when, by complete accident, you kill Santa Claus? You take over the job, of course! 1994's "The Santa Clause" stars Tim Allen as Scott Calvin, who travels to the North Pole where he's given the news that because he's inadvertently responsible for Santa's demise, he must permanently take on the role himself!
"While You Were Sleeping" on Disney+, YouTube & Apple TV
In 1995's "While You Were Sleeping," recluse transit employee Lucy (Sandra Bullock) saves Peter (Peter Gallagher), her longtime crush, from an oncoming train. While in a coma, the doctors and Peter's family mistake her for his fiancée. To complicate matters even further, Lucy begins to fall for Peter's brother, Jack (Bill Pullman). Talk about a tangled web!
