Christmas with the Kranks (2004)

With their daughter off with the Peace Corps, a couple (perennial Xmas fave Tim Allen and a shockingly mousy Jamie Lee Curtis) decides to skip Christmas. But they soon discover their community isn't down with that idea. When plans change at the last minute, the mad dash to deck out the holiday hearth begins... and hilarity more or less shuffles in. Trivia: the movie is based on a novel, Skipping Christmas, by John Grisham (!) king of the legal thrillers.
 Deck the Halls (2006)

File under "so bad it's good," a kind of tinsel-coated Battlefield Earth. Danny DeVito and Matthew Broderick star as warring neighbours vying to be the undisputed "Christmas guy" in their 'hood. Critically panned, the film is worth a peek to see if it meets this evaluation by film critic Richard Roeper of Ebert & Roeper fame: "You cannot believe how excruciatingly awful this movie is. It is bad in a way that will cause unfortunate viewers to huddle in the lobby afterward, hugging in small groups, consoling one another with the knowledge that it's over, it's over -- thank God, it's over." Seriously, don't you want a little piece of that with your eggnog?
Four Christmases (2008)

When a couple's plan to abscond on vacation over the holidays goes awry, they must scramble to visit all four of their divorced parents in one day. Lots of movies capitalize on the theme of weird relatives but few have done it better... or with a better cast. Leads Reese Witherspoon and Vince Vaughn are spot-on as the beleaguered offspring of Jon Voight, Mary Steenburgen, Sissy Spacek and Robert Duvall - all Oscar winners. The film also reunites Vaughn with Swingers alum Jon Favreau - rarely a bad combination.
Jingle All the Way (1996)

A dad's last-minute attempt to land the most coveted toy on his son's Christmas list - and every other kid's list that year - propels him down a slapstick highway populated by malevolent reindeer, violent elves, wise-cracking neighbours and, uh, Sinbad. Starring a pre-gubernatorial Arnold Schwarzenegger at his most histrionic as well as the late, great Phil Hartman, this movie goes down surprisingly well despite its dog-eared premise.
The Santa Clause (1994)

Oh Tim Allen - what would the holidays be without you? Santa-less for one thing. When a dad trying to please his son dons a Santa suit, he is transformed into Saint Nick for real and no amount of protestation can turn the tide. Talk about being married to the job. Allen perfectly captures the horror of a man morphing against his will into an obese, bearded child magnet powerfully attracted to shortbread.
Home Alone (1990)

A monster hit on release and a perennial fave year after year, this film made Macaulay Culkin a star and features Joe Pesci as something other than a Mob-connected thug, albeit still a bad guy. Accidentally left behind by his vacationing parents, an enterprising kid fends off would-be burglars with increasingly ingenious strategies... after playfully exploring all the possible adventures an unsupervised eight-year-old can enjoy around the house. Catherine O'Hara provides a Canadian connection as the frazzled mother who will stop at nothing to return to her missing son.
National Lampoon's Christmas Vacation (1989)

No holiday would be complete without a visit from the Griswolds and their unhinged extended family. Oh the broken windows! The burnt turkey! The electrocuted cat! The homicidal squirrel! The third film in the Vacation series and the only one to have hatched its own direct-to-video sequel: National Lampoon's Christmas Vacation 2: Cousin Eddie's Island Adventure with Randy Quaid. Sorry, probably too much information.
A Christmas Story (1983)

The story is by now well-known: more than anything else in the world, young Ralph covets an official Red Ryder carbine-action 200-shot range model air rifle. But the whole world, it seems, is conspiring to keep him away from one, fearing he'll shoot his eye out. Few movies have so much awesome trivia associated with them: though set in Indiana, it was mostly filmed in Cleveland with extra shots gathered in Toronto and St Catharines; a house in Cleveland decorated like the fictional Parker family home is now operating as a museum; actor Peter Billingsley who plays the title role of Ralphie is now a director - he manned 2009's Couple's Retreat. He also continues to have Christmas film connections: he appears uncredited in Elf and plays a bit part as a ticket agent in Four Christmases which he also exec-produced. Phew.
Elf (2003)

As if the mere presence of Will Ferrell in tights and pointy shoes isn't enough, director Jon Favreau generously gives filmgoers one of the most classic fish-out-of-water premises in filmdom: a human raised by elves at the North Pole travels to New York City to track down his father and begin a new life. With about a million sight gags, killer one-liners and several genuinely side-splitting scenes (including one with actor Peter Dinklage as a so-called "angry elf" taunted by Farrell's character Buddy), Elf has wall-to-wall laughs AND Ed Asner as Santa. Beat that.
Bad Santa (2003)

Not just the hands-down funniest Christmas movie ever (though it is that), Bad Santa ranks as one of the funniest movies ever made. Slingblade, Schmingblade - Billy Bob Thornton's crowning achievement is as the thieving, foul-mouthed, alcoholic, degenerate, borderline-child-abusing department store Santa who, along with diminutive sidekick Marcus, unleashes crime on unsuspecting middle America every holiday season. Ingeniously cast with John Ritter and Bernie Mac (R.I.P. guys) as the men bent on bringing Thornton's Santa to justice and Cloris Leachman as the catatonic grandma to The Kid who sincerely believes Santa can right the world's wrongs. If this movie doesn't make you pee your pants, you're probably dead... or possibly in need of more cider.