Top 10 Movie Christmas Capers

by Warren Cantrell on December 15, 2015

in Top 10s

There’s an odd, weirdly cozy relationship between Christmas and crime, at least in cinema. Hollywood’s scribes churn out “holiday” films on the regular, and since conflict drives story, nefarious doings often get stirred into the plot-stew of Yuletide yarns. Today’s list ranks the various Christmas capers that have popped up in Christmas films throughout the years, and judged them based on their creativity, ultimate success, and quality of presentation. In other words, depending on how well-thought-out, successful, and entertaining a Christmas caper was, along with the quality of the movie that showcased it, the better its ranking below.

To qualify for consideration, the film and its Christmas crime had to take place on either the 24th or 25th of December, and in a setting that was indeed celebrating the birth of Jesus Christ. It takes a proper scoundrel to exploit what is meant to be a charitable holiday rooted in notions of camaraderie and fellowship, so in the spirit of the holidays, Scene-Stealers elected to give these rogues their due. As always, if you feel a particularly fun Christmas caper was left out of today’s discussion, feel free to leave a comment below. Until then…

10. L.A. Confidential (1997)

L.A. Confidential took a number of unexpected turns throughout the course of its runtime, yet many of the events cascaded from a nasty little incident that took place at a police station on Christmas Eve. After a couple of officers got scraped up in an encounter with a handful of Hispanic suspects, word got back to the boys at the precinct, where the Christmas party was in full swing (with spiked punch a-flowin’). The assault suspects were brought into that very same station, where one of the more wobbly officers, Det. Dick Stensland (Graham Beckel), got himself and a gaggle of other officers worked up into a punching mood. Stensland led a gang of cops into the lockup area for a little payback on the perpetrators, where the officers unloaded on the Hispanic suspects with a fury that only armed public servants can fully harness.

Rotten luck fell atop the heads of these custodians of justice, however, as a couple of reporters just happened to be on hand when all hell broke loose, and, well…pictures were taken. Terminations and suspensions were handed out like candy on Halloween, thus the caper was not an especially successful one (unless measured in blood and bruises). Still, it takes a pretty big set of balls to go after incarcerated suspects in custody with newspaper men around, so for that, and the especially high quality of the film and the performances, L.A. Confidential got the opening nod.

9. National Lampoon’s Christmas Vacation (1989)  

Not so much a caper as a spur of the moment psychotic break, the assault and kidnapping that Eddie Johnson (Randy Quaid) perpetrated on Christmas Eve in National Lampoon’s Christmas Vacation was indeed a transgression worth mentioning today. After hosting a multi-day, multi-generational family Christmas reunion, Clark Griswold (Chevy Chase) was running on fumes. His kids weren’t invested in the experience, his in-laws took every opportunity to undercut his well-intentioned efforts at holiday cheer, and his greasy cousin suddenly and unexpectedly got thrown into the mix. Critical failures at several key junctions throughout the holiday had Clark on edge, for his Christmas light display gave him endless trouble, his turkey was ruined, and a mean old bastard burned down his tree. On top of all that, Clark’s boss stiffed him on his expected Christmas bonus, which meant a pool Clark had been angling to buy would likely ruin him (financially, if not morally).

In a fit of desperation, Clark mentioned that what he really wanted for Christmas was to have his boss brought to his home so he could tell him, “what a cheap, lying, no-good, rotten, four-flushing, low-life, sack-licking, dirt-eating, inbred, overstuffed, ignorant, blood-sucking, dog-kissing, brainless, dickless, hopeless, heartless, fat-ass, bug-eyed, stiff-legged, spotty-lipped, worm-headed sack of monkey shit he is!” Cousin Eddie obliged, and kidnapped Clark’s boss, which brought a S.W.A.T. team down on Clark’s house. Thus, it wasn’t exactly a sophisticated or even successful caper, yet it did take place in a modern holiday classic, and everyone got off in the end, and got their just rewards. For that, this one slid in at #9.

8. Trading Places (1983)  

When you take away a man’s home, job, beloved, and dignity, all that’s left is a desperate, dangerous shell of a person. That was exactly the case for Louis Winthrop III (Dan Aykroyd) in Trading Places, which told the story of two crusty old commodities brokers who wagered that a person’s success or failure was (or was not, depending on the bet) determined by social factors, and not genetics. To test their theory, they purposefully ruined one of their best employees, Louis, by framing him for a crime that saw him arrested, fired, and dumped. This scheme also financially ruined him, and forced him to shack up with a Manhattan prostitute who had a minor, indirect hand in ruining his life. Meanwhile, a hobo was plucked off the street and put in Louis’ place (Eddie Murphy at his very best), and over the course of a few weeks, each displaced man more or less assumed the identity of the other.

The shocking reversal of fortune finally drove Louis to the brink on Christmas Eve, when he dressed up like Santa, infiltrated his old company’s offices, and attempted to plant drugs in his rival’s desk. Although creative, it was a poorly conceived plan that was busted even before it got off the ground, yet it took place in one of the most beloved Christmas movies of the last half-century. If Louis had been more successful in his machinations, at any stage, this one might have beat out…

7. Home Alone (1990)  

This was a difficult one to rank, for while the “Wet Bandits” seemed fairly successful in their operations prior to running up against a pre-pubescent foil, their modus operandi didn’t exactly scream sophistication. In Home Alone, Joe Pesci played Harry, a B&E specialist who liked to pose as a cop to case houses via a direct conversation with the homeowner under the guise of checking up on their security protocols. Once Harry hashed out what kind of alarms and security features a residence had, he and his partner robbed the place after the family left for a Christmas holiday.

Although this straightforward ruse seemed profitable enough for them, the whole works went to pieces when Harry and his sidekick, Marv (Daniel Stern), encountered a young kid who had been accidentally left behind, all alone, for Christmas. This kid, Kevin (Macaulay Culkin), just happened to be a Rube Goldberg-esque genius when it came to traps designed for home defense, and fended off the would-be robbers on Christmas Eve (albeit with a little help from a friendly neighbor). Home Alone is now a holiday film staple, and while Harry and Marv weren’t exactly pulling off an intricate series of heists, they were largely successful until they ran into the world’s youngest recorded super-sadist. For that, they slid in at #7, just behind…

6. The Ice Harvest (2005)  

Stealing from the mob is always a dicey proposition, but when you throw in double and triple crosses amongst the perpetrators, you’ve got an unholy mess on your hands. In The Ice Harvest, Charlie (John Cusack) and Vic (Bill Bob Thornton) played a couple of tangential mob associates looking to make a quick Christmas Eve score. Although their plan to steal $2,000,000 from the local mob boss went off without a hitch, a sudden snowstorm rolled in and iced up the roads leading out of town. Thus, right at the time Charlie and Vic needed to put some distance between themselves and the murderous mob boss looking to flay them, they were forced to stay put and lay low.

This was especially tough on Charlie, who used this time to try and wrap up some personal business that included chasing after a stripper romance, mending ties with his children, and helping out an old friend (that happened to be married to his ex-wife). Things went off the rails when the full scope of Vic’s plan started to unfold before Charlie, who realized his partner and the stripper he was trying to screw were in cahoots and planning to put him six feet under once the opportunity presented itself. As far as the criteria of today’s list, The Ice Harvest got high marks for quality of performance and overall picture, along with the fact that as far as Charlie was concerned, the heist was indeed ultimately successful. Yet the sophistication of the script was in the double-crosses, not the caper itself, which relegated this one to #6, one spot behind this next film, where things were a tad less successful (not to mention fatal)…

5. Trapped in Paradise (1994)  

The first of two 1994 entries on today’s list, there was obviously something in the air that year which inspired Christmas-themed mischief. Trapped in Paradise told the story of the Firpo brothers, a trio of scoundrels whose morals all registered somewhere on the scale between bad and evil. Bill Firpo (Nic Cage) started the movie on the straight and narrow, yet was quickly pulled into the shenanigans of his brothers Alvin (Dana Carvey) and Dave (Jon Lovitz). Although they were on parole, Alvin and Dave convinced the half-reformed Bill to travel with them to Paradise, PA, where they planned to roll a soft country bank.

The clincher? The robbery would take place on Christmas Eve, when the bank would be at its fattest: a plan the three of them miraculously pulled off despite a tripped alarm and a high-speed chase. As far as plan complexity, the brothers didn’t exactly break new ground with their approach (ski masks, guns, strong-arm tactics), but their repeated ability to evade capture and the noose did set them apart from many of the other candidates listed today (none of the brothers went to jail, after all). Yet all the money was eventually returned, and without the passive assistance of Paradise’s townsfolk, all three Firpo brothers would have ended up in the clink for at least 10-20. Now, for a more successful robbery in an even better film out of 1994, we ought to turn to…

4. The Ref (1994)  

A hidden gem from the mid-90s, The Ref was a lot better than it had any right to be, and sported a cast of just-about-to-break stars that were all just coming into their own.  In the film, Dennis Leary played a burglar named Gus, who was putting the finishing touches on a home invasion/jewel heist on Christmas Eve when an alarm system tripped, and dumped him into the house’s basement (with the guard dog). Although he managed to get away from the house in one piece, and without handcuffs, his partner and getaway driver bailed on him and left Gus looking for an alternate escape route. This led Gus to Caroline (Judy Davis) and her husband Lloyd (Kevin Spacey), perhaps the most combative couple in North America circa 1994.

As for the heist itself, Gus did pretty well for himself considering the fact that he got the loot, escaped the scene of the crime, and eventually made it to freedom (albeit after suffering through a torturous evening of familial drama crossing several generations). Although the audience didn’t get much of a look at Gus’ prep work in advance of the job, the fact that he navigated through what appeared to be one hell of a thorny security system and got away boosted his case considerably, and put him at #4, just behind another less charming thief…

3. Bad Santa 

This was a tough one to beat, for the foundation of this film’s premise was rooted in a caper that was exclusive to Christmas, and the opportunities America’s preferred consumer-oriented holiday affords. In Bad Santa, Willie T. Stokes (Billy Bob Thornton) ran a yearly scam whereby he and his partner posed as a department store Santa and a helper elf so that they could gain easier access to shopping malls and rob them after the Christmas Eve holiday shutdown. It was a decent plan, and seemed to have served the duo well over several successful holiday seasons, yet as Bad Santa started, the audience learned that Willie’s sex addiction, alcoholism, aggressive depression, and general nastiness threatened the operation. Yet after he formed a mentorship bond with a local kid, and hooked up with a bartender harboring a fierce Santa fetish, Willie got a new lease on life, and seemed to turn a corner.

Unfortunately for him, Willie’s helper elf partner double-crossed him on the night of the mall heist, and everything went to shit. Willie eventually got off on a technicality, as everyone agreed that, “the police department shooting an unarmed Santa was even more fucked up than Rodney King.” While Bad Santa as a film was a goddamned hoot, and the caper was successful over a period of years (only to fall apart at the end), it was hardly a Swiss watch. Now our runner-up entry, it had moving parts enough that only a legendary “fly in the ointment” could have derailed it…

2. Die Hard (1988)  

As legendary as Die Hard has become over time due to the franchising of John McClane (Bruce Willis), it is easy to forget that the original caper at Nakatomi Plaza was a meticulously planned, wonderfully executed (mostly), professional operation from top to bottom. Hans Gruber (Alan Rickman) assembled a top-notch mercenary squad to infiltrate a multinational corporation after-hours on Christmas Eve, a sneaky yet brilliant plan. This was done so that the only people in the building would be staff of the chosen company they intended to rob, staff that would be needed either to crack the vault code, or act as hostages during phase two of the plan. This second phase involved getting into protracted negotiations with the L.A.P.D., who would eventually have to turn to the F.B.I., who were needed to act as a patsy for the roof explosion that would eliminate any unneeded hostages.

This in turn was meant to create chaos below for the police trying to contain the situation, and act as a diversion so that Hans, his team, and any select hostages could escape via ambulance. All this was possible because Hans had disguised his caper as a political act of terrorism rather than a high-end heist, which he almost certainly would have pulled off if not for one rogue cop named John mutha-fuckin’ McClane. It was a magnificent, complex plan in one of the greatest action movies of all time, and came within an inch of being successful. For that, it came within an inch of the #1 spot, held down by…

1. How the Grinch Stole Christmas (2000) 

There’s robberies, assaults, kidnappings, and old fashioned terrorism on Christmas (all of them, rotten acts), and then there’s a direct assault on the very institution itself. As our nine previous examples have demonstrated, the latter cases are indeed deplorable exercises in humanity’s ever-evolving capacity for cruelty, but to actually try and steal Christmas: that’s breaking all sorts of bad. In Ron Howard’s live-action version of Dr. Seuss’ classic How the Grinch Stole Christmas, The Grinch (Jim Carrey) lived atop Mt. Crumpit, and harbored a burning hatred for the nearby town of Whoville and its residents. Howard’s version gave a healthy dose of back-story to the Grinch that provided some context for his grudge against the townsfolk, but the end result was the same: the Grinch resolved to steal Christmas and all the joy that came with it.

The Grinch was successful in the first phase of his plan, at least as it concerned his perception of the material importance of the holiday. With the stealth of a seasoned cat burglar, The Grinch broke into every house in Whoville, and stole all the presents, along with most of the decorations associated with festivities. But when the sour old bastard realized that Christmas was about more than simple possessions and consumerism, that Whoville’s holiday spirit endured despite the Christmas Eve caper, The Grinch had a breakthrough. Redeemed, The Grinch returned his plunder and changed his ways, yet before doing so, one has to remember that The Grinch executed one of the most audacious, sweeping robbery-sprees in movie history. That, combined with the goodwill that still lingers from the original 1966 T.V. special, earned this one the #1 spot.

“Obvious Child” is the debut novel of Warren Cantrell, a film and music critic based out of Seattle, Washington. Mr. Cantrell has covered the Sundance and Seattle International Film Festivals, and provides regular dispatches for Scene-Stealers and The Playlist. Warren holds a B.A. and M.A. in History, and his hobbies include bourbon drinking, novel writing, and full-contact kickboxing.


Leave a Comment


Previous post:

Next post: