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Home / Blog / 20 Classic and Unexpected Picks to Watch with Your Teen Boys this Holiday Season

20 Classic and Unexpected Picks to Watch with Your Teen Boys this Holiday Season

Written by Christine Derengowski

As some boys get older, it gets harder to get them in the holiday spirit. They might begrudgingly drive around to look at Christmas lights with you. They’ll definitely eat your holiday treats but may no longer want to help you make and decorate them.

It’s hard to get them to enjoy the things they used get so excited about doing as a family. And holiday movie night is no exception, especially since so many holiday-themed movies center around romance or target younger children.

But we refuse to let this tradition go by the wayside. If you’re having a hard time getting your tween or teen boy to hunker down and watch a movie with you this holiday season, try some of these holiday classics that our teen boys still enjoy or some of these holiday-adjacent blockbusters that are wildly entertaining yet still offer a little festive cheer.

Put on your holiday jammies, turn down the lights, and watch by the Christmas tree glow. (Snacks are not optional.)

You may also like to read: 25+ Christmas Traditions For Families With Tweens and Teens

Traditional Holiday Movies

Christmas Vacation

This slapstick Christmas comedy never gets old. As Clark Griswold tries to orchestrate the “perfect old-fashioned family Christmas,” his plans unravel due to misadventures with a massive tree, 25,000 exterior lights, unannounced extended house guests like Cousin Eddie, and a delayed holiday bonus.

Watch on Prime


Home Alone

A family comedy without the family! Kevin McCallister is accidentally left home alone while his family flies to Paris for the holiday. He initially enjoys his freedom before realizing he must protect his home from two bumbling burglars known as the “Wet Bandits.”

Watch on Prime


Candy Cane Lane

Chris Carver wants to win his town’s decorating contest so he makes a deal with a mischievous elf. But chaos ensues when his decorations come to life, wreaking havoc on their town.

Watch Free Here


Elf

Laugh along with your teens as Buddy the Elf, a man raised by Santa’s elves, travels from the North Pole to New York City to meet his biological father who doesn’t know he exists.

Watch on Prime


Red One

In this new action-packed classic, Santa Claus (code-named Red One) is kidnapped from the North Pole. His unorthodox Head of Security, Callum Drift (Dwayne Johnson), must team up with infamous bounty hunter and tracker Jack O’Malley (Chris Evans) on a globe-trotting mission to save Red One and Christmas.

Watch On Prime


Scrooged

A coldhearted TV executive gets a hard lesson on the true meaning of Christmas in this wild, woolly, and modern retelling of Dickens’ “A Christmas Carol.”

Watch on Prime


Daddy’s Home 2

Reformed co-parents Brad (Will Ferrell) and Dusty (Mark Wahlberg) plan a joint family Christmas. Their plans are disrupted when their own contrasting fathers—Dusty’s macho, old-school dad, Kurt (Mel Gibson), and Brad’s affectionate, sensitive father, Don (John Lithgow)—arrive for the holidays.

Watch on Prime

For more traditional holiday favorites, you may also like The Best Christmas Movies to Get Your Teens to Snuggle on the Couch Again

Non-Traditional Holiday Movies

Die Hard

NYC police detective, John McClane, travels to LA to visit his wife during her Christmas Eve office party only to have the celebration interrupted by heavily armed criminals.

Watch on Disney


Shazam!

Set during the holiday season, a newly fostered young boy in search of his mother finds he has unexpected super powers… and a powerful enemy.

Watch on Prime


Iron Man 3

Driven by its holiday setting, Iron Man 3 is the third installment in the blockbuster series where Tony Stark faces a new enemy who uses explosive Extremis technology. Might as well make it a Marvel marathon! All are available on Disney.

Watch on Disney


Rocky IV

Blaming himself for the tragic death of his friend, Rocky Balboa accepts a challenge to fight Drago in an unsanctioned bout in Moscow on Christmas Day. This is another great series to binge with your teens if they haven’t watched Rocky 1-3.

Watch on Prime


Enemy of the State

Will Smith stars as a lawyer who is unknowingly slipped an incriminating video by an old acquaintance while Christmas shopping. He soon finds himself fleeing from a rogue National Security agent in this action-packed thriller.

Watch on Prime


Harry Potter Series

While not technically holiday movies, the Harry Potter series certainly has a Christmassy feel. It’s a nostalgic holiday tradition in many households to watch these movies throughout the season. Watch them all free with a Peacock subscription or on Prime.

Watch on Prime


Catch Me If You Can

The plot of this biographical cat-and-mouse crime drama spans multiple years and tracks the recurring Christmas Eve phone calls between con man Frank Abignale Jr. and FBI agent Carl Hanratty.

Watch on Prime


Lethal Weapon

A veteran cop and an unstable detective become partners who must put aside their differences in order to catch a gang of drug smugglers. The action takes place during the holidays making this another seasonal must-watch for teen boys.

Watch on Prime


Are We There Yet?

To impress their mom, Nick offers to escort his crush’s kids on a 350 mile road trip following Christmas where he is forced to endure their wildly mischievous antics.

Watch on Netflix


Hawkeye

In this Marvel universe series, Clint Barton, aka Hawkeye, must team up with skilled archer Kate Bishop to unravel a criminal conspiracy and get home to his family in time for Christmas.

Watch on Disney

Holiday Horror Movies for Older Teens

Gremlins

A gadget salesman finds a special Christmas gift for his son, an adorable mogwai he names Gizmo. When he breaks three strict rules for its care, a horde of violent gremlins unleash havoc on their small town.

Disclaimer: This movie is more gruesome than we remember from watching it as kids.

Watch on Prime


Krampus

After a dysfunctional family squabble ruins his holiday, a boy named Max loses his Christmas spirit and inadvertently summons Krampus, the demonic spirit who punishes the naughty at Christmas.

Disclaimer: This movie is more horror than holiday and not for younger teens or tweens who scare easily.

Watch on Prime

Violent Night

HEAVY DISCLAIMER: this movie lives up to its name- it is violent and very gruesome so this movie is not for everyone.

When a team of elite mercenaries attempts to rob a wealthy family on Christmas Eve, they encounter an unexpected adversary: Santa Clause.

Watch on Netflix

Parenting teens and tweens is hard work. These posts other parents found useful may help make it a little easier.

Some Teenagers Just Need a Little Push to Join the Holiday Magic

100+ Awesome Gift Ideas For Teen Boys for 2026

The Absolutely Best Stocking Stuffer Ideas for Teen Boys in 2026

15 of The Best Movies On Netflix for Teen Boys

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Christine Derengowski

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