The 2000s: a time of questionable fashion, the dawn of iPhones, and some pretty amazing holiday movies. The 1980s and 1990s brought fans some great stories, iconic characters, and the clear progression of technology throughout, but the 2000s brought an amazing collection of festive movies that celebrate the holiday season. Even though there are plenty of holiday movies to binge-watch on streaming channels, the 2000s brought some really great gems.
The 2000s gave us movies that were full of quotes, family dysfunction that mostly worked out by the end credits, and R-rated Santas behaving badly. If viewers haven't sunk their teeth into these gems yet, it's the perfect time to indulge and binge-watch a few of them on a cold day.
Four Christmases - 5.7 (2008)
Sometimes plans don't work out for the holidays and when Brad, played by Vince Vaughn, and Kate, played by Reese Witherspoon are on their way to Fiji for Christmas, things don't quite work out. When their plans fall through, they decide to visit their four sets of parents, all divorced and remarried.
Each family is completely different from one another and the couple realizes that even though they know a lot about their past, they might not know enough. Even though Four Christmases isn't one of Vince Vaughn's best movies to date, his role as Brad is hilarious and works well with Witherspoon's character.
How The Grinch Stole Christmas - 6.2 (2000)
In late 2000, director Ron Howard decided to re-vamp the classic story of Dr. Seuss's How the Grinch Stole Christmas. Instead of a cartoon, Howard recreated it as a live-action film and brought in Jim Carrey as The Grinch and Taylor Momsen as Cindy Lou Who.
With Carrey's iconic reputation and stellar acting, he led the film, How the Grinch Stole Christmas, to massive success, as a revenge-seeking Grinch who plans to ruin Christmas for all the fellow citizens of Whoville. This isn't one to miss, and once viewers watch it, it'll be a tradition for years to come.
Halloweentown II: Kalabar's Revenge - 6.4 (2001)
Following the 1998 Disney Channel Original Halloweentown, the sequel follows Marnie Piper living in the real world and her grandmother Aggie, who lives in Halloweentown. The two work together to foil the plans of a wicked warlock's son named Kal, before he can use powerful spells to create unwarranted chaos in the world.
The Halloweentown franchise has conjured up some pretty spooky characters and just in the first two Halloweentown movies alone, there are some powerful characters that wreak havoc in one way or another.
The Family Stone - 6.3 (2005)
The Family Stone is a romance, drama, and comedy all rolled into one and stars Dermot Mulroney, Sarah Jessica Parker, and Claire Danes. When an upright businesswoman named Meredith Morton goes home with her fiance Everett Stone, played by Mulroney, she discovers his immediate family is eccentric and outgoing, completely different from herself.
While the movie is filled with comedic relief, the storyline is realistic, awkward, and at times, hard to watch. The Family Stone is a movie filled with an A-list cast, and realistic situations that any family might have to deal with, which makes it relatable.
Trick 'R Treat - 6.8 (2007)
Trick 'r Treat is a unique movie that came out in 2007 and gained popularity because it really took the anthology concept and ran with it, but also made sure all five stories are interwoven with each other.
Each story occurs on Halloween and includes a high school principal who's a serial killer, a college student who meets the "man of her dreams," teenagers pulling mean pranks, a woman who hates Halloween, and an old man with an attitude who finds his match when an unsuspected visitor intrudes in on his night.
What's Cooking? - 6.9 (2000)
The Thanksgiving holiday doesn't get as much love as other holidays do when it comes to the movie industry, but when Gurinder Chadha released What's Cooking? in 2000, it received rave reviews. When four Los Angeles families get together for a Thanksgiving dinner, tensions arise.
Each family has its own secrets and issues, and they come out to play when they're all under one roof. The cast is great, the storyline is interesting, and above all, it's relatable for all families who watch it.
Elf - 6.9 (2003)
If someone you know struggles with getting into the holiday spirit, Elf is the movie to push on them. The 2000s brought a lot of great Christmas movies, but without a doubt, Elf is one of the best for a lot of reasons. Directed by Jon Favreau, after a human-sized elf named Buddy decides he's not cut out for The North Pole, he goes to the great city of New York to find his real father.
In Elf, Will Ferrell plays Buddy, and it's one of his most iconic roles to date. It's for the entire family and tells a story about family, believing in something, and embracing one's inner child.
Bad Santa - 7.0 (2003)
There are a lot of family-friendly movies about Santa and the holiday season, but when it comes to Bad Santa, it definitely isn't for the whole family. Starring Billy Bob Thornton, the story focuses on a miserable conman named Willie, played by Thornton, who poses as Santa, and with an elf as side-kick, they plan to rob a department store on Christmas.
Of course, not everything goes as planned, and Willie ends up at rock bottom and unsuspectedly befriends a troubled kid. Even though Bad Santa isn't for kids, it's a tragic comedy that adults will get a laugh at.
A Dog Named Christmas - 7.4 (2009)
Hallmark movies can be really good or really cheesy and when it comes to A Dog Named Christmas, it's one of the better movies to come from the channel. It's a family drama that tells the story of a developmentally challenged boy who loves taking care of animals.
When he sets his sights on the local shelter's inaugural "Adopt a Dog for Christmas Program," he has to convince not only his family to participate, from the entire rural community to chip in. It's heartwarming and a great movie to watch with the family around the holidays.
Love Actually - 7.6 (2003)
When a movie fan wants to enjoy a romantic comedy to watch over the holidays, they'll more than likely turn to Love Actually. The storyline follows the lives of eight very different couples that are dealing with their love lives in loosely related ways.
All set a month before the holidays in London, England, each story is interesting on its own and stars Hugh Grant, Liam Neeson, Emma Thompson, Colin Firth, and Bill Nighy. Love Actually was and still is so popular around the holidays, that it is surprising it wasn't amongst the nominated films of the 2000s.