01 ‘Elf‘ (2003)
This loopy movie is the sweet and silly tale of a human baby raised by elves at Santa’s North Pole home. Jump ahead to adulthood and our boy, played by Will Ferrell, heads to New York City to find his biological father, played by James Caan. Along the way, he picks up some elf work and a little romance. It’s a goodhearted, modern-day fairytale loaded with charm and daffy slapstick—enough to delight kids and even grumpy ol’ middle-aged guys. Also starring are Mary Steenburgen, Zooey Deschanel, Bob Newhart, Ed Asner, and Andy Richter.
02 ‘A Christmas Story‘ (1983)
Peter Billingsley’s Ralphie dreams and schemes to be gifted with a glorious Red Ryder air rifle—at the risk of shooting his eye out. Based on narrator Jean Shepherd’s “In God We Trust, All Others Pay Cash,” this is a loving remembrance of life as it was lived in the 1940s. Yet, the challenges Ralphie faces are just as pertinent, compelling, and hilarious today. And who could forget the frozen-pole-and-tongue scene?
03 ‘Scrooged‘ (1988)
“Scrooged” is a contemporary remake of the Charles Dickens classic “A Christmas Carol,” in which Ebenezer is a heartless television executive named Frank Cross, played by Bill Murray. When Frank fires an employee, played by comedian Bobcat Goldthwait, on Christmas Eve, a series of freaky but funny ghosts turn up to give him a tour of his past, present, and future.
04 ‘Miracle on 34th Street‘ (1947)
This movie is a classic in every sense of the word. A department-store Santa claims to be the real deal. To prove it, he lands in court, converting a skeptical six-year-old, played by Natalie Wood, into a believer. The comic fantasy won three Oscars, including Original Story, Best Screenplay, and Best Supporting Actor for Edmund Gwenn as Kris Kringle.
05 ‘Home Alone‘ (1990)
Almost everyone knows the story: Eight-year-old Kevin McCallister accidentally gets left behind when his family goes to Paris for Christmas, and hijinks ensue. Using only his wits, a cunning Kevin must protect his home from two bumbling criminals who are hell-bent on pulling a Grinch and stealing everything in sight. Pratfalls and sight gags galore pepper what has become one of the most popular movies of all time—and it made a star out of Macaulay Culkin as Kevin.
06 ‘National Lampoon’s Christmas Vacation‘ (1989)
Everybody’s favorite globe-trotting goofballs, the Griswolds, stay home for the traditional American family Christmas. Experience the tree, the outdoor lights, the dinner, the uninvited relatives (including Cousin Eddie!)—all the recognizable hells of the season. Well-done slapstick and trademark tastelessness stuff the package, starring Chevy Chase and Randy Quaid.
07 ‘Bridget Jones’s Diary‘ (2001)
“Bridget Jones’s Diary” begins and ends on New Year’s day. In the course of one year, we ride along with the incorrigible Bridget as she finds love, loses love, makes blue soup, and finally finds love again. This movie is filled with laughs and irresistible characters. Oh, and ugly Christmas sweaters, too.
08 ‘When Harry Met Sally‘ (1989)
As college students, Harry Burns (Billy Crystal) and Sally Albright (Meg Ryan) meet by chance when they share a ride home for the holidays. When they get reacquainted 10 years later, they discover whether or not women and men can ever really “just be friends.” A classic during any time of the year—and who can forget the diner scene!—it’s especially fun during the holidays, since the final scene takes place on New Year’s Eve, a night full of new beginnings for even the oldest of friends.
09 ‘The Santa Clause‘ (1994)
Tim Allen plays a divorced dad who accidentally kills a man in a Santa suit on Christmas Eve. He’s then magically transported to the North Pole, where he finds out that he has killed the REAL Santa and must now take over Santa’s duties. When he gains a “bowl full of jelly” belly overnight and grows that iconic white beard, he finally realizes that this was no dream.
10 ‘Jingle All the Way‘ (1996)
It’s “The Terminator” for tots, as Arnold Schwarzenegger goes to any extreme to score an unobtainable toy for his kid’s Christmas commandment. Big and splashy, the production will suit youngsters—and parents who’ve been there, done that. Sinbad becomes a villain, of sorts, competing in the chase, while smarmy neighbor Phil Hartman chases Arnold’s wife, played by Rita Wilson.
11 ‘It’s a Wonderful Life’ (1946)
This favorite Christmas movie of many is largely a drama, but since it’s such an iconic holiday film, it must be included on this list. Laced with homespun humor and post-WWII Americana, Frank Capra’s brilliant film—which was based on a Christmas card—is often warm, fuzzy, and funny. Could anything possibly be more satisfying than the romance of James Stewart’s George and Donna Reed’s Mary? The black-and-white photography is beautiful, too.
12 ‘How the Grinch Stole Christmas‘ (2000)
The famous ugly schmuckling charges onto the screen in full blustery weirdness, doing his grinch-ey thing amid intentionally laughable art direction. So, who in Whoville has been a good little boy? That wouldn’t be greeny meany Jim Carrey, a sourball of holiday-loathing. The movie is a delight to watch in part for the actor’s body language, which is sharply considered and executed and results in an impressive physical comedy performance.
13 ‘Trapped in Paradise‘ (1994)
Inept criminals played by Jon Lovitz and Dana Carvey con their disapproving brother (Nicolas Cage) into becoming an accomplice on a Paradise, Pennsylvania, bank robbery. Unfortunately, the icy weather delays the trio’s getaway, forcing them to experience the gracious Christmastime hospitality of their victims. An easygoing surprise, which meshes chuckles with golden-era Hollywood inspiration.
14 ‘Bad Santa‘ (2003)
Fair warning: This comedy is dark. Every year, two con men, played by Billy Bob Thornton and Tony Cox, team up to pose as a mall Santa and his elf in order to steal from the shops in the mall. Yet when Thornton’s Santa shows up drunk and depressed, a security guard (the late, great Bernie Mac) catches on to their schemes. Then a young boy enters the scene to really mix things up, and “Bad Santa” discovers the true meaning of Christmas.
15 ‘Trading Places‘ (1983)
Filthy rich elitist investment broker brothers Mortimer (Don Ameche) and Randolph Duke (Ralph Bellamy) make a bet: Can down-and-out criminal Billy Ray Valentine (Eddie Murphy) become a successful banker if given the chance? And what happens when pampered snob Louis Winthorpe III (Dan Aykroyd) has his fortune taken away and given to Valentine? After the Dukes frame Winthorpe for a crime he didn’t commit and Valentine catches on, the two men work together to take down the scheming Dukes. The movie also co-stars Jamie Lee Curtis as a smart hooker with heart—and love of—gold.