20 Best Christmas Movies Of The 2000s

Christmas movies have been around for decades, but the early 2000s were home to some of the best Christmas movies. Those years brought along some mediocre films, but there are plenty of great ones from the time too. That particular decade offered moviegoers lots to get excited about when it came to the holidays.

New holiday films come out each year, but some of the Christmas movies from the 2000s are already considered classics. Some of these films have even become holiday traditions for families around the world. Here are some of the best 2000s Christmas movies.

Updated Dec. 19, 2021 by Amanda Bruce: Classic Christmas movies are nostalgic even for those who don’t celebrate the holiday. There’s something to be said for the feel-good comfort of a familiar story with a happy ending. With such a large number of 2000s Christmas movies, both for television and theatrical release, there’s a plethora of quality holiday magic from the decade. Some of them are stories of family and finding the spirit of the season, while others are love stories that hit just the right mark.

20 The Ultimate Christmas Present (2000)

• Available to stream on Disney Plus

A Disney Channel Original Movie, The Ultimate Christmas Present features two teenage girls who find a miraculous weather machine they use to bring snow to Los Angeles. As it turns out, the machine malfunctions, and one of the girls discovers her dad is going to be stuck at the airport for Christmas as a result of the blizzard they caused. The machine, of course, belongs to Santa Claus himself, who has to track it (and the girls) down.

This movie has such a unique and fun concept that kids who grew up with it would watch it for years after its initial broadcast date. While it offers to teach kids a lesson, like a lot of early 2000s Christmas movies, it’s still a rare gem among light Disney Channel fare.

19 Holiday In Handcuffs (2007)

• Available to stream on Hulu

Back when it was still called ABC Family, Freeform aired an original movie titled Holiday in Handcuffs, in which a struggling artist succumbs to the pressure of bringing a date home for the holidays by kidnapping one of the customers at the restaurant where she works.

The concept is a little troubling, but the movie makes up for its problematic premise with a lot of humor and heart. Melissa Joan Hart and Maria Lopez have great chemistry together, and that’s largely what makes it so fun to watch.

18 Ghosts Of Girlfriends Past (2009)

• Available to rent on Youtube

While not strictly a Christmas movie, Ghosts of Girlfriends Past draws its inspiration from one of the most popular Christmas stories of all time: A Christmas Carol. The movie follows Connor Mead as he attends his brother’s winter wedding and relives the relationships of his past through his first girlfriend, his assistant, and his deceased uncle.

A Christmas Carol has become something of its own holiday trope as even television shows use it in their holiday episodes. This particular movie provides a new twist on the idea as Connor isn’t particularly greedy or selfish, simply afraid of falling in love. Of course, the movie is made even better with some stellar casting with Emma Stone as Connor’s first girlfriend, Jennifer Garner as the woman he’s always been in love with, and Matthew McConaughey as Conner himself.

17 Serendipity (2001)

• Available to stream on Netflix

Though the movie takes place over several years, it begins its story with two people shopping for Christmas presents. Jonathan and Sara meet when they both want to purchase the same pair of gloves. While they’re interested in each other, they’re both involved in other relationships, so Sara decides they should leave their potential next meeting up to fate, writing her number in a book, and his on a five-dollar-bill, and waiting to see if either find their way back to them.

Serendipity is a frustrating series of missed connections between the two main characters. Every time the audience thinks their paths will cross, they just miss one another, but that’s part of what makes the audience engaged. After all, the premise is a little far-fetched, movie fans want that happy ending. It’s incredibly gratifying when the book and the money finally reemerge in the story.

16 A Diva’s Christmas Carol (2000)

• Not available to stream

Like Ghosts Of Girlfriends Past, A Diva’s Christmas Carol provides its own twist on the classic Charles Dickens story. Made for VH1, the movie stars Vanessa Williams as the titular diva, a singer who is visited by three ghosts that get her to see just where her life is headed.

Because the movie was made for VH1, it features plenty of singing courtesy of Vanessa Williams and former TLC member Rozonda “Chilli” Thomas. The focus on music, stardom, and how it can change someone gives the movie a different feel than simply focusing on a wealthy man who doesn’t want to give his employees time off. Unique takes on stories the audience already knows always make for a good time.

15 The Holiday (2006)

• Available to stream on Hulu

The Holiday is a surprisingly deep and lovely holiday rom-com with a lot of layers to each relationship on screen. Kate Winslet and Cameron Diaz star as two women who have completely had their hearts broken right before the holiday and decide to house swap for the season as Diaz travels to England and Winslet travels to California.

Diaz meets Jude Law’s character while Winslet meets Jack Black’s character and although the two weren’t looking for love, it adorably finds them. It’s certainly one of the best Christmas movies of the 2000s that just happens to double as a fun rom-com.

14 Just Friends (2005)

• Available to stream on Netflix

Just Friends follows a successful music producer (Ryan Reynolds) who is forced to travel home for the holidays after the famous pop star (Anna Faris) he’s traveling with ruins her private jet. He runs into his old high school crush (Amy Smart) and he decides to “friend zone” her for revenge but realizes that he still has feelings for her.

The premise is a little dated, but it’s still a fun and at times hilarious movie with great holiday decorations and a great cast led by Ryan Reynolds.

13 Unaccompanied Minors (2006)

• Available to stream on Netflix

Unaccompanied Minors follows a group of kids who are stranded in an airport over the holidays when the weather gets bad and they can’t continue to travel on their own.

The kids try their best to have a fun holiday even though they’re stuck in the airport from driving golf carts through the terminals to looking for presents in the lost baggage area. The tightly wound airport official (Lewis Black) and his assistant (Wilmer Valderrama) try to catch them throughout the days they’re stuck there.

12 Eight Crazy Nights (2002)

• Available to stream on IMDbTV

Adam Sandler stars in this animated movie and voices several different characters including the main character, Davey, who is given one more chance to get his life together by doing some community service volunteering or be put in jail. He meets his eccentric partner, Whitey Duvall, also volunteering as a referee for the local youth basketball league.

It’s raunchy and in line with the rest of Sandler’s work, but isn’t as well known and perfect for any fan of his during the holiday season.

11 Last Holiday (2006)

• Available to rent through Amazon

Queen Latifah stars in this Christmas rom-com that has a serious and dramatic edge to it. Her nervous and content character works at a department store and loves to cook and bake in her spare time but doesn’t actually end up eating her meals or take chances anywhere else in her life.

Everything changes when she gets a terminal diagnosis and she finally takes a chance traveling to Europe to meet her favorite chef. It’s a movie with beautiful scenery and a beautiful message, and the potentially tragic premise certainly sets it apart from other 2000s Christmas movies.

10 How The Grinch Stole Christmas (2000)

• Available to stream on Peacock

The live-action version of How The Grinch Stole Christmas is a remarkable movie, thanks to the stellar performances that the entire cast managed to put on. Though the story is not an original concept, this film is pure magic. How The Grinch Stole Christmas is excellent at reminding viewers how exciting Christmas can be.

Another cool thing about it is the evident hard work that went into creating Whoville. This film also features one of Jim Carrey’s best performances, which is often underrated compared to his other films. That being said, many people consider Carrey’s portrayal of the Grinch as one of the highlights of the movie.

9 The Family Man (2000)

• Available to rent on Youtube

Nicholas Cage and Téa Leoni truly shine in the movie The Family Man. They play characters named Jack Campbell and Kate Reynolds. This film is basically like the reverse version of another classic holiday movie, It’s A Wonderful Life.

That is because, in this mo, Jack gets a glimpse of what his life would have been like if he had stayed home and married Kate instead of traveling and becoming a wealthy businessman. This film was released in December of 2000, and it is a really underrated movie. It makes one think about how different their lives could be if they had made different decisions.

8 The Polar Express (2004)

• Available to stream on HBO Max

The Polar Express was released back in 2004, and it is a truly great animated film. While the animation probably makes it seem as though this movie is only aimed at children, there are plenty of reasons why adults will likely enjoy it as well.

The movie is very visually appealing from start to finish, and Tom Hanks voices many of the characters. One of them, the conductor of the train, even looks a lot like the famous actor. This movie is a lot of fun, and it certainly appeals to everyone who has ever had a serious passion for Christmas – or kids who grew up reading the book in school.

7 Elf (2003)

• Available to stream on HBO Max

Elf might be the most recognizable of early 2000s Christmas movies. This movie stars Will Ferrell in one of his most memorable roles to date, and it is actually hard to imagine anyone else playing that part since he did it so well.

This story is a lot different than the stories most Christmas movies seem to have. It is about an elf who learns who his real dad is, so he travels from the North Pole to New York so that he can meet him in person. It has the same heart of a lot of other holiday films, but the premise is certainly unique.

6 Christmas With The Kranks (2004)

• Available to rent through Amazon

Tim Allen has starred in a number of great Christmas movies, and Christmas With The Kranks is undoubtedly one of them. The two stars of this movie are Allen and Jamie Lee Curtis, both of which deliver exceptional performances as Luther and Nora Krank. Dan Aykroyd is another well-known star that plays a big part in this movie.

They decide to go on a cruise and skip Christmas since their daughter no longer lives at home. However, her decision to visit them over the holidays throws a wrench in their plans. This movie also has a surprisingly touching ending.

5 Bad Santa (2003)

• Available to stream on Pluto TV

Bad Santa is another excellent Christmas movie that came out in the 2000s. This movie is very different from others that are like it because of the fact that it is not a family-friendly film. However, that didn’t stop it from quickly becoming a classic movie that everyone loves after it was released in 2003.

This movie is about an alcoholic man who gets jobs as a Santa Claus in different locations every year in order to rob stores. He forms a close bond with a young boy, which changes him for the better. In short, the movie is full of hilarious adult humor.

4 Love Actually (2003)

• Available to rent on Youtube

Love Actually is a very enchanting and funny Christmas film that was released in American movie theaters on Nov. 14, 2003. One of the reasons why this film is so great is because of the star-studded cast that it features.

Some of the stars in the film include Keira Knightley, Andrew Lincoln, Martin Freeman, Liam Neeson, and Colin Firth, among many other famous people. There are some truly iconic scenes in this movie, including the one where Andrew Lincoln’s character tells Keira Knightley’s how he feels about her or the fantastic school musical number.

3 Deck The Halls (2006)

• Available to stream on HBO Max

Deck The Halls was released on Nov. 22, 2006. The main characters are brilliantly portrayed by Danny DeVito, Matthew Broderick, Kristin Davis, and Kristin Chenoweth.

This movie is about two families that live next door to each other. Broderick’s character, Steve, always decorates a lot for Christmas, but when DeVito’s character, Buddy, comes into the picture, he gives Steve a serious run for his money as far as Christmas decorating goes. Though they do not get along throughout much of the movie, their children form some pretty close friendships.

2 The Family Stone (2005)

• Available to stream on Peacock

The Family Stone was released in 2005 and is another entry that is unlike other Christmas movies. This movie has some really humorous moments, but the film is rather serious for the most part.

This movie is one that is probably much more appealing to adults than it would be to children, unlike some other Christmas films. The Family Stone is basically about an uptight, career-oriented woman learning how to live a little when she spends Christmas with her boyfriend’s family. Those who have not seen it should know that the ending is something most viewers would not expect.

1 Four Christmases (2008)

• Available to stream on HBO Max

Four Christmases came out in November of 2008 and is all about the chaos that Christmas can sometimes bring. Reese Witherspoon and Vince Vaughn play Kate and Brad, a couple who ends up having to visit all of their family members on Christmas, instead of taking the vacation that they had initially planned on.

The only problem with that is the fact that both of them have parents that are divorced, so they have to celebrate Christmas four different times. Some of the other stars in the movie include Dwight Yoakam, Tim McGraw, Kristin Chenoweth, and Robert Duvall.

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