Movies like Pee-wee's Playhouse Christmas Special (1988)
The best movies like Pee-wee's Playhouse Christmas Special (1988) are Merry Christmas, Drake & Josh (2008), Dolly Parton's Christmas on the Square (2020) and To Grandmother's House We Go (1992). If Pee-wee's Playhouse Christmas Special hooked you with its family and comedy, these 30 similar films are what to watch next, and every pick says why it matches.
Quick picks
- Highest ratedA Charlie Brown Christmas (1965)7.7/10 from 824 votes
- Newest31 Minutes: One Hot Christmas (2025)Released 2025
Merry Christmas, Drake & Josh (2008)
Step brothers Drake and Josh must give a foster family the best Christmas ever or face years in jail for a Christmas party gone wrong.
Why it matches: Recommended by TMDB viewers · both comedy & family
Worth the HypeMovies like thisDolly Parton's Christmas on the Square (2020)
A rich and nasty woman returns to her hometown to evict everyone but discovers the true meaning of Christmas thanks to the local townsfolk – and an actual angel. Features 14 original songs with music and lyrics by Dolly Parton!
Why it matches: Recommended by TMDB viewers · both comedy & family
SnoozefestMovies like thisTo Grandmother's House We Go (1992)
When precocious twins Sarah and Julie feel like Mom is tired of them, they take off on an exciting adventure to their grandmother's house and encounter a pair of villains along the way.
Why it matches: Recommended by TMDB viewers · both family & comedy
Popcorn FlickMovies like thisKristin's Christmas Past (2013)
Kristin, a cynical 34-year-old, drinks a mysterious champagne on Christmas Eve and wakes up seventeen years in the past, sharing a room with her 17-year-old self. Given the chance to change the worst Christmas of her life, she attempts to fix past mistakes, only to discover surprising truths about her family that may help her mend her present-day relationships.
Why it matches: Recommended by TMDB viewers · both comedy & family
SnoozefestMovies like thisMickey and Minnie Wish Upon a Christmas (2021)
After a series of mishaps, Mickey, Minnie and the gang are separated all over the world and must try to get back to Hot Dog Hills by Christmas Eve. A mysterious and jolly stranger shows up to tell them about The Wishing Star, which could be the secret to bringing everybody home in time to celebrate together.
Why it matches: Recommended by TMDB viewers · both comedy & family
Worth the HypeMovies like thisA Charlie Brown Christmas (1965)
When Charlie Brown complains about the overwhelming materialism that he sees amongst everyone during the Christmas season, Lucy suggests that he become director of the school Christmas pageant. Charlie Brown accepts, but it is a frustrating struggle. When an attempt to restore the proper spirit with a forlorn little fir Christmas tree fails, he needs Linus' help to learn the meaning of Christmas.
Why it matches: Recommended by TMDB viewers · both family & comedy
Worth the HypeMovies like thisCharlie Brown's Christmas Tales (2002)
Tis the season for the cheer and charm of the Peanuts kids - and this delight special offers five segments full of unforgettable moments. Snoopy works as a bell-ringer to raise money and tries making peace with the ferocious cat next door. Linus strives to strike the right tone in his letter to Santa - and his friendship with an indecisive girl at school. Sally's idea about gift giving and the identity of Santa may be unusual - but her strange notion about how to obtain a Christmas tree surprisingly does the job. Lucy tries awfully hard to be nice...and still coax everyone around her to buy her presents. Charlie Brown and Sally wait up for Santa (a surprisingly short man), who spreads Christmas gift cheer further than they had thought. Make merry!
Why it matches: Recommended by TMDB viewers · both comedy & family
Popcorn FlickMovies like thisA Flintstones Christmas Carol (1994)
Fred is cast as Ebenezer Scrooge in a stage adaption of the classic Christmas story, but is acting a bit stingy in real life.
Why it matches: Recommended by TMDB viewers · both comedy & family
Popcorn FlickMovies like thisIt's Christmastime Again, Charlie Brown (1992)
As the holiday season rolls around and all the Peanuts gang are getting ready for it. Whether it be Charlie Brown struggling to raise money for his girlfriend or Sally and Peppermint Patty struggling to rehearse and memorize their one word lines for the Christmas pageant, these kids try to keep with the Christmas spirit while Snoopy has his mischief to do.
Why it matches: Recommended by TMDB viewers · both family & comedy
Popcorn FlickMovies like thisCandy Cane Lane (2023)
Determined to win the neighborhood's annual Christmas decorating contest, family man Chris makes a pact with an elf to help him out-do the competition. However, the elf casts a spell bringing the twelve days of Christmas to life, unleashing chaos on the small unsuspecting town.
Why it matches: Recommended by TMDB viewers · both comedy & family
Popcorn FlickMovies like thisClick & Collect (2018)
To save his daughter's Christmas, Andrew goes on a road trip with Dev, his neighbour from hell, to buy an elusive Sparklehoof the Unicorn Princess.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisMagic Stocking (2015)
A young widow finds a tattered old Christmas stocking at a Holiday craft sale, but is skeptical of its magic when it seems to create small trinkets on its own.
Why it matches: Recommended by TMDB viewers · both family
Popcorn FlickMovies like thisThe Christmas Note (2015)
Having just moved back to her hometown without her serviceman husband but with her young son, Gretchen Daniels finds her life in disarray as Christmas approaches. But she discovers new purpose when she helps to deliver a message to her neighbor, Melissa, which makes her an ally in the quest to find the neighbor's sibling she never knew she had. The women become bonded not only by the search, but by the understanding that being there for each other means they're no longer alone. This friendship becomes the greatest Christmas gift of their lives. Based on a bestselling novel by Donna VanLiere.
Why it matches: Recommended by TMDB viewers · both family
Popcorn FlickMovies like thisBah, Humduck!: A Looney Tunes Christmas (2006)
In this adaptation of Charles Dickens' A Christmas Carol, Daffy Duck is the greedy proprietor of the Lucky Duck Mega-Mart and all he can think about is the money to be made during the holiday season.
Why it matches: Recommended by TMDB viewers · both comedy & family
Worth the HypeMovies like thisThe Trailer Park Boys Xmas Special (2004)
In this holiday prequel, it’s 1997 and Sunnyvale Trailer Park is getting ready for the holiday season. Julian’s got a great idea to make money this Christmas, Ricky gets confused between God and Santa, and Bubbles tries to get the Boys together for an annual Christmas bonfire. Meanwhile, Mr. Lahey is thrilled because Christmas is the only day of the year that his wife Barb allows him to have a few drinks. Directed by series creator Mike Clattenburg, this hour-long special takes place before Jamie was J-Roc, before Randy and Lahey were a couple, and before the Shitmobile was missing a door.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisMickey's Magical Christmas: Snowed in at the House of Mouse (2001)
When a huge snowstorm leaves everyone stranded, Mickey and all of his guests at the House of Mouse, including Pooh, Belle, Snow White, Cinderella, Ariel and many more of his old and new friends, break out the cookies and hot chocolate to help Donald mend his tattered Christmas spirit.
Why it matches: Recommended by TMDB viewers · both family & comedy
Worth the HypeMovies like thisA Christmas Story Christmas (2022)
Follows Ralphie, now adult, who returns to the house on Cleveland Street to give his kids a magical Christmas like the one he had as a child, reconnecting with childhood friends, and reconciling the passing of his Old Man.
Why it matches: Recommended by TMDB viewers · both comedy & family
Popcorn FlickMovies like thisBeethoven's Christmas Adventure (2011)
A Christmas elf accidentally takes off in Santa's sleigh, crash lands in a small town, and loses the magic toy bag. Beethoven must rescue the elf, recover the bag from greedy crooks, and return the sleigh to Santa in time to save Christmas.
Why it matches: Recommended by TMDB viewers · both family & comedy
Popcorn FlickMovies like thisA Scooby-Doo! Christmas (2002)
On the way to Daphne's relatives' condominium, the Mystery Inc. gang detours through the town of Winter Hollow, where the vengeful Headless Snowman has destroyed the town's Christmas spirit.
Why it matches: Recommended by TMDB viewers · both family & comedy
Absolute CinemaMovies like thisScooby-Doo! Haunted Holidays (2012)
Scooby-Doo and the gang participate in a toy store's holiday parade where they discover the abandoned haunted clock tower with a troubled past. A sinister snowman haunts the streets and accompanied with a large blizzard, threatens to close down the toy store for good.
Why it matches: Recommended by TMDB viewers · both comedy & family
Absolute CinemaMovies like thisHow the Grinch Stole Christmas (2000)
The Grinch decides to rob Whoville of Christmas - but a dash of kindness from little Cindy Lou Who and her family may be enough to melt his heart...
Why it matches: Similar story and style · both family & comedy
Popcorn FlickMovies like thisThe Santa Clause 2 (2002)
Better watch out! The big guy in red is coming to town once again. This time, Scott Calvin -- also known as Santa Claus -- finds out there's an obscure clause in his contract requiring him to take on a wife. He has to leave the North Pole to fulfill his obligations, or else he'll be forced to give up his Yuletide gig.
Why it matches: Similar story and style · both comedy & family
Popcorn FlickMovies like thisChristmas à la Carte (2021)
When food correspondent, Carly, gets a shot at her own show, she is sent to Angel Heights to help Grant open his diner and film it as a Holiday special for her TV show. Will Grant and Carly open their hearts too?
Why it matches: Similar story and style · both comedy
The Bad Guys: A Very Bad Holiday (2023)
To keep their annual Holiday Heist-tacular afloat, Mr. Wolf and his crew of animal outlaws will have to restore the whole city's Christmas spirit — fast!
Why it matches: Similar story and style · both comedy & family
Popcorn FlickMovies like this31 Minutes: One Hot Christmas (2025)
Puppeton, the town of 31 Minutes, faces such an infernally hot Christmas that Santa Claus cancels his visit! Bodoque the rabbit heroically volunteers to rescue the presents from the North Pole, while his friends improvise a disastrous Christmas show. But what they don't expect is Bodoque giving in to some irresistible temptations along the way.
Why it matches: Similar story and style · both family & comedy
Christmas Crush (2012)
Twenty-eight-year-old Georgia is convinced the man of her dreams is "the one that got away" back in high school. When Georgia learns of her high school reunion a week before Christmas, she's ecstatic to finally have her chance to win Craig back. But as she gets to relive high school for a night, she begins to realize it might not be Craig at all who got away, but Ben, an old friend with whom she'd fallen out of touch.
Why it matches: Similar story and style · both comedy
SnoozefestMovies like thisChristmas by the Book (2022)
An author of a best selling holiday book becomes entangled in tinsel when she and her kids are dispatched by a TV talk show to a rural town where she is given two weeks to recreate the magical childhood Christmas described in her book.
Why it matches: Similar story and style · both comedy
The Action Pack Saves Christmas (2022)
The Action Pack teams up with Santa Claus to save the day when greedy Teddy Von Taker plots to steal all of the Christmas cheer from Hope Springs.
Why it matches: Similar story and style · both family
The Family Stone (2005)
An uptight, conservative businesswoman accompanies her boyfriend to his eccentric and outgoing family's annual Christmas celebration and finds that she's a fish out of water in their free-spirited way of life.
Why it matches: Similar story and style · both comedy
Popcorn FlickMovies like thisA Christmas Tale (2008)
When their regal matriarch falls ill, the troubled Vuillard family come together for a hesitant Christmastime reunion. Among them is rebellious ne'er-do-well Henri and the uptight Elizabeth. Together under the same roof for the first time in many years, their intricate, long denied resentments and yearnings emerge again.
Why it matches: Similar story and style · both comedy
Popcorn FlickMovies like this
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Frequently asked questions
What are the best movies like Pee-wee's Playhouse Christmas Special?
The closest matches to Pee-wee's Playhouse Christmas Special are Merry Christmas, Drake & Josh (2008), Dolly Parton's Christmas on the Square (2020) and To Grandmother's House We Go (1992). Below are 27 more, each with the reason it matches.
What should I watch after Pee-wee's Playhouse Christmas Special?
Start with Merry Christmas, Drake & Josh (2008), the closest match to Pee-wee's Playhouse Christmas Special.
What is the highest-rated movie like Pee-wee's Playhouse Christmas Special?
A Charlie Brown Christmas (1965), rated 7.7/10 by 824 TMDB users.
What is the newest movie like Pee-wee's Playhouse Christmas Special?
31 Minutes: One Hot Christmas (2025) is the most recent release on this list.
Are there English movies like Pee-wee's Playhouse Christmas Special?
Yes: Merry Christmas, Drake & Josh (2008), Dolly Parton's Christmas on the Square (2020) and To Grandmother's House We Go (1992).
How are movies similar to Pee-wee's Playhouse Christmas Special chosen?
First come films that Trakt’s viewers watch alongside Pee-wee's Playhouse Christmas Special, then TMDB’s recommendations and films it rates as similar in story and genre. Each pick says which signal put it there.