Press "Enter" to skip to content

The Best Guilty Pleasure Holiday Movies

The Best Guilty Pleasure Holiday Movies

Not all movies are made for the critics. On occasion, some films are made to simply hit a sweet spot, giving us the basic, unapologetic dose of dopamine we humans tend to crave. 

Many people have a select set of films that make them crack a smile, acting as comfort food to end a stressful day. Although some may fear the judgements of others should they discover such technically unsound, narratively challenged, horrifically acted and/or cheaply produced films are in our regular rotations, they are nonetheless impossible to resist.

During the holiday season, festive movies cross the screens of millions, evoking joyous feelings and a whiff of nostalgia. Such Christmas-centric films include “A Christmas Story,” a film so popular it has fueled 24-hour marathons on basic cable. But we’re not gathered here today to talk about such classics — instead, this list is comprised of films a few rungs lower on the ladder. These are the movies you watch alone, the movies you profess love for only when surrounded by your closest confidantes. These are the guilty pleasure movies of the holiday season.

Jingle All the Way (1996)

Children of the late nineties were chanting “It’s turbo time!” as they watched this holiday flick featuring action star-turned-family-friendly-funnyman Arnold Schwarzenegger. While this goofy flick was decimated by critics and became an easy punchline for late night comedians, the film has since maintained warm remembrances for its wildly campy depictions of tough-guy Schwarzenegger confronting an unfortunate string of failures and bad luck while attempting to secure the most sought-after toy of the holiday season for his son: a Turbo Man action figure. 

As Schwarzenegger’s beleaguered dad-seeking-redemption battles an obnoxious mail man nemesis (Sinbad), the two see civility and any semblance of Christmas spirit go out the window, all as they try desperately to win the affection of their children. The film is fueled by a myriad of slapstick and “Three Stooges”-esque violence, and when coupled with Arnold’s over-the-top mugging, it certainly isn’t for all tastes. But there’s also a solid, heartwarming story at the core of “Jingle All the Way” that will delight daring viewers seeking out the comfort of a family movie experience — and a few laughs in the process.

Deck the Halls (2006)

In a similar vein to “Jingle All the Way,” this family comedy with a solid supporting cast (Fred Armisen, Alia Shawkat, Kristin Chenoweth, Kristin Davis) employs camp and cheesy humor to depict a humorous, sometimes cutthroat war between neighbors. The film stars Matthew Broderick as Steve Finch and Danny DeVito as his neighbor Buddy Hall.

 Steve takes pride every year in being known around town as an enthusiastic Christmas nerd; Buddy is an unfulfilled car salesman with a desire to make his home visible from outer space. 

What ensues is a battle to put together the biggest Christmas display the neighborhood has ever seen. As the movie spirals into an all-out war between the two neighbors, the antagonistic relationship between Broderick and DeVito (who has made a career out of playing “mean” in films like “War of the Roses” and “Other People’s Money”) fuels some solid fun. Sure, “Deck the Halls” was DOA at the box office upon its release, and the film can be wincingly overbearing at times with its dialogue. However, if you’re looking for something new to watch this holiday season, you could do worse.

Eight Crazy Nights (2002)

Produced by Adam Sandler’s Happy Madison Productions, “Eight Crazy Nights” marked the funnyman’s first time dabbling in animation — a medium that would eventually give him the immensely-successful “Hotel Transylvania” series.

Sandler plays an outcast who leans hard on the bottle, as well as troublemaking antics in the small town of Dukesberry, New Hampshire. After finding himself in legal trouble, he is spared a prison sentence after an older gentleman by the name of Whitey Duvall (also Sandler) intervenes, pleading with the judge to allow Davey to perform community service for Whitey’s basketball league for youth. The judge allows it and Davey begins his service, albeit with sarcasm and disdain.

It quickly becomes apparent that Davey is expressing a lot of pain from his past by causing problems with the locals. Despite Whitey’s willingness to help him, Davey seems to always travel down a more self-destructive path. This holiday film, a rare one that feels like a Christmas movie but is centered around Hanukkah (much like Sandler’s classic 1995 “carol” “The Chanukah Song”), is heart-warming, tragic at times, and as unapologetically goofy as you’d expect from an Adam Sandler movie. 

Sure, lots of people don’t like it — but then again, lots of people don’t like every Adam Sandler movie — but if you share his sense of humor, this criminally underrated cartoon could be your next guilty pleasure.

Bad Santa 2 (2016)

The 2003 Terry Zwigoff comedy “Bad Santa” became a holiday mainstay almost immediately upon its release, casting Billy Bob Thornton as a rude, crude mall Santa in what might be the raunchiest holiday film ever made. But don’t sleep on its long-delayed sequel “Bad Santa 2,” which didn’t land the same way with audiences or critics, but is deserving of a second look.

Once again, Willie Soke (Thornton) finds himself in a lowly place as an alcoholic whose streak of bad luck and depression brings him back into the life of Thurman Merman (Brett Kelly), the rotund kid who latched onto Willie in the first film. Now 21-years-old, Merman gives Willie a package full of cash from his old partner Marcus (Tony Cox), who is now fresh out of prison after the events of the prior film. Once again, the two partner up — this time, with Willie’s estranged mother (Kathy Bates) on the scene. 

Like its predecessor, “Bad Santa 2” wields the sort of crude humor and jaded wit that will have you laughing from a rare place: shock. Critics knocked the sequel for attempting to up the ante on the original film’s vulgarity, but without the same heart (likely due to not only having a different director, but writers as well). Nevertheless, if you’re a fan of the original, it’s mandatory viewing.

Christmas with the Kranks (2004)

Has the stress of the holiday season ever tempted you to just skip it altogether? Well, if not, it certainly happened to Luther (Tim Allen) and Nora Krank (Jamie Lee Curtis). 

After their daughter leaves for the Peace Corps in Peru, they decide to do away with the festivities, decorations, and gifts and go on a cruise instead. Little do they know that their lack of Christmas spirit will draw the ire of the neighborhood, who expect to be decorated for the season. Fate strikes when the Krank family’s daughter Blair (Julie Gonzalo) calls to tell them she’s coming home with a Peruvian fiancé in tow as a Christmas surprise.

Frantically, the Kranks attempt to throw together Christmas by decorating, borrowing a neighbor’s Christmas tree, and shopping. Since Blair expected her parents to hold the traditional neighborhood party they host every year, they throw that together as well — resulting in a manic chaos as they slap Christmas together at the 11th hour. 

Believe it or not, the film is based on a John Grisham novel called “Skipping Christmas.” Like some of the other films on this list, “Christmas with the Cranks” became both a critical punching bag and a Hollywood punchline, yet it’s not nearly as bad as it is made out to be. Give it a chance — but just be sure to draw your shades tight, lest the neighbors catch you watching a Tim Allen Christmas movie that doesn’t have the words “Santa Clause” in the title.

Ernest Saves Christmas (1988)

During the late ’80s and early ’90s, Jim Varney was a bona fide phenomenon, as his Ernest P. Worrell — a goofy, verbose everyman with a southern twang and a never-speaking friend in the “Vern” he addressed by looking at the camera — went from regional commercials all the way to ten cheaply-produced, high-grossing movies and a Saturday morning cartoon show. 

Of course, Ernest celebrates the holidays just like the rest of us. So, in his second film (after 1987’s “Ernest Goes to Camp”), he’s driving a taxi and happens upon a man who claims to be the Santa Claus (Douglas Seale). The naive Ernest takes him at his word, and when it turns out to be true, Santa explains that he must pass the mantle on to someone else, a local children’s program host by the name of Joe Caruthers (Oliver Clark).

Santa doesn’t have any cash on him, and when kind-hearted Ernest doesn’t charge Saint Nick, he is fired from his job. But as luck would have it, the jolly man left his magical sack in the car, so Ernest sets out to find Santa and return the precious cargo to him. 

Like every “Ernest” movie, the premise wasn’t going to earn a place in any screenwriting class curriculums. But also like the other films in the franchise, Varney’s charm goes a long way, and the result is an enjoyable, family-friendly flick. “Ernest Saves Christmas” performed well in the box-office, but was of course considered a critical failure; give “Ernest” a chance, and you be the judge.

I'll Be Home for Christmas (1998)

Jonathan Taylor Thomas became a household name playing Randy Taylor on the 1991-1998 Tim Allen sitcom “Home Improvement.” His acting career peaked in the ’90s with roles in some other shows and films (including being the voice of young Simba in Disney’s “The Lion King”), but 1998 may have earned his most notable solo moment when he headlined “I’ll be Home for Christmas” alongside a young Jessica Biel. 

Cast as a freshman in college on the west coast, JTT’s character hasn’t returned to his home in New York since his father remarried after his birth mother died in a tragic event. In order to bribe his son home for Christmas, dad offers him a Porsche if he arrives in time for Christmas dinner on Christmas Eve. In other words, it’s a very relatable movie.

Driven by his desire to secure the car, Jake (Thomas) plans to travel to New York with his girlfriend Allie (Biel). But when he doesn’t honor a deal to help a fellow student cheat on an exam, Jake is dumped in the desert, dressed as Santa Clause. At this point, the flick becomes a holiday road trip, with the character on a cross-country quest with a ticking time clock. 

On the one hand, this is a preposterous movie starring a long-faded ’90s hearththrob. On the other, it’s an endearing, harmless little movie that might just elicit a few unexpected smiles as Jake stumbles across the country and attempts to learn a lesson or two about what is really important.

How The Grinch Stole Christmas (2000)

Thanks to all those years of repeated holiday viewings, everybody knows the 1966 Grinch and his devious plans to steal Christmas from the whos down in Whoville. 

In the year 2000, Ron Howard took on the instantly-divisive task of adapting the 26-minute animated classic into a 104-minute live action movie, with Jim Carrey cast as the furry green grump. Naturally, the film added multiple new layers to the Dr. Seuss classic, resulting in a somewhat awkward, yet sometimes endearing story about a social outcast’s attempt to regain acceptance among his peers.

Jim Carrey’s eccentricities were dialed all the way to ten in this film, instilling a cartoony aesthetic into a character who was supposed to be going the other way. While the live-action gimmickry might have ultimately hurt the film with critics, it nevertheless retains the heart of the Grinch story, and with a talented cast and standout soundtrack, it is worth watching after you’ve watched the 1966 “Grinch” a dozen times and want something that takes the story to a different level.

Home Alone 2: Lost in New York (1992)

Often, sequels that attempt to rehash the magic captured in the original film are seen as cash grabs that focus on shaking down fans of the first film over originality. However, it’s a hard argument to make when it is apparent that fans willing to pay for a sequel are likely seeking more of the same thrills, albeit in a different coat of paint. That’s exactly what “Home Alone 2: Lost in New York” offers.

It’d be neglectful (and perhaps even criminal) if the McCallister parents once again left their son home alone, so this time Macauley Culkin is striking out on his own in the big city. After a pre-9/11 era void of security, Kevin is able to mistakenly lose his ticket at the airport, not provide an ID, and board a plane to the wrong destination without an accompanying guardian. This sends his family to Florida and him to New York City where — what a coincidence! — he just happens to encounter the dimwitted burglar duo he thwarted in the first film (Joe Pesci and Daniel Stern) fresh off a prison break. 

Yes, it’s all absurd, as is Kevin’s need to once again employ an array of booby traps to torture the baddies and save the holiday. But if you enjoyed the original film, “Home Alone 2” could be a solid holiday season guilty pleasure.

Four Christmases (2008)

Everyone has at least one dysfunctional family member who they hate the idea of spending Christmas with for fear of misery and drama. Well, Kate (Reese Witherspoon) and Brad (Vince Vaughn) both have families full of dysfunction. So, they never spend Christmas at home and instead plan vacations elsewhere — until one fateful Christmas, when the two are stuck home for the holiday as their plane is grounded due to fog. Their families see them on the news, and now that everyone knows they’ll be home for the holidays, the couple are obligated to endure all the family trappings.

Ultimately, their Christmas Day is broken up into four separate Christmas celebrations, because all these parents have divorced, with many of these get-togethers further complicated by trouble-making siblings and wild children. 

Another holiday film that was seen upon its release as a huge dud (especially considering the two leads, both at peak popularity), “Four Christmases” certainly isn’t anything mind-blowing. But it is a fun, average Christmas-centric film offering more smiles, laughter, and heart than you expect.

Daddy's Home 2 (2017)

Ever since “The Other Guys,” Mark Wahlberg and Will Ferrell have made a fun comedy duo with chemistry that lights up audiences, even if the movie doesn’t always hit home with critics. 2015’s  “Daddy’s Home” was a humorous tale about a stepfather (played by Ferrell) seeking the approval of his stepchildren — whose biological father (Mark Wahlberg) comes back into their lives, launching a competition between the two for the children’s affection. 

By the end of that first film, the two dads had formed a bond, both resolving to be great dads in their own unique ways. “Daddy’s Home 2” takes place during Christmas, adding their fathers (Mel Gibson and John Lithgow) into the mix for the holiday celebrations. 

While the film has a good number of laughs at the expense of its characters, it isn’t all goofball shenanigans. “Daddy’s Home 2” saves a moment among the chaos to find the spirit of the season bringing families together. The bottom line: If you like the original “Daddy’s Home,” you shouldn’t ignore the sequel.

The Holiday (2006)

Out of all the films listed here, Nancy Meyers’ “The Holiday” might be closest to shedding its “guilty pleasure” label and ascending to the level of genuine classic.

Holding it back, most likely, is the film’s cliché rom-com trappings, along with a too-obvious ploy to bring together unlikely couples in a quirky, unusual manner. While one can argue that all rom-coms fall into the same pitfalls, “The Holiday” leans hard into its “fish out of water” trope, revolving around two bachelorettes who recently experienced bad break-ups due to unfaithful boyfriends and decide to house swap for two weeks in order to escape their lives. 

Iris Simpkins (Kate Winslet) lives in London and is a columnist for a newspaper. Amanda Woods (Cameron Diaz) is a movie trailer producer who resides in Los Angeles. The two make the switch and ultimately get wrapped up in each other’s lives. Amanda begins to fall for the brother of Iris (Jude Law), while Iris begins dating a colleague of Amanda’s ex-boyfriend (Jack Black). The two couples ultimately enjoy the holiday season living outside of their own lives while discovering unlikely romances in another part of the world. Is it littered with typical rom-com tropes? Yes. Is the swap a bit gimmicky? Yes. But does the film manage to spark a sense of romantic adventure through its gimmick that will ultimately satisfy avid viewers of the genre? Most certainly.

Be First to Comment

Leave a Reply

Your email address will not be published.