10.) The Santa Clause / Batman and Robin

Child actor Eric Lloyd played the lovable Charlie Calvin in The Santa Clause and then went on to play young Bruce Wayne in the colorful and perhaps, awesomely bad, Batman and Robin. Think of it this way: Spending time at the North Pole followed by an evening with Mr. Freeze should put anyone in the spirit for snow and holiday décor. Or, you could always pop in Serenity after The Santa Clause and watch Bernard the Elf (David Krumholtz) as Mr. Universe.

9.) Miracle on 34th Street / American Horror Story

What? You haven’t seen Season One of American Horror Story? Now’s your chance to heat up hot chocolate, watch the 1994 version of Miracle on 34th Street where Dylan McDermott defends the existence of the fantastical, and afterwards, watch as he faces the less-loving spirit world in American Horror Story.

8.) How the Grinch Stole Christmas! / Frankenstein

Why not spend a night revisiting two American classics that both feature Boris Karloff? Perhaps start off with Karloff as the ultimate featured creature in Frankenstein and end with his iconic narration telling us “the Grinch thought of something he hadn’t before. Maybe Christmas, he thought . . . doesn’t come from a store. Maybe Christmas, perhaps . . . means a little bit more!”

7.) Serendipity / Hot Tub Time Machine

If rom-coms are typically not your thing, perhaps sitting through a snow-filled romantic romp starring John Cusack won’t be so bad if followed by the wintery, raunchy, time-traveling comedy Hot Tub Time Machine, which also stars Mr. Cusack.

6.) Home Alone / The Nightmare Before Christmas

With an unforgettable cast, including Macaulay Culkin, Joe Pesci, Daniel Stern, Catherine O’Hara, and John Candy, Home Alone is practically mandatory holiday viewing. Try pairing Catherine O’Hara screaming “Kevin!” with her stand-out voiceover performance as Sally and Shock in the atmospheric, Tim-Burton-ified The Nightmare Before Christmas.

And/or, pop in Diner to put your coming-of-age holiday drama quota over the edge. Daniel Stern as a grouchy burglar who gets more than his share of beatings in Home Alone coupled with his performance as a young man finding his way in Diner is a no-brainer. (Oh and speaking of Diner . . . Kevin Bacon!)

5.) It’s a Wonderful Life / Rear Window

It’s a Wonderful Life is one of the best holiday movies ever made, but perhaps pairing it with another James Stewart classic, Rear Window, will give your evening newfound suspense and excitement. Break out the scotch and a warm blanket, it’s time for a classy holiday evening!

4.) The Thing / Miracle

In the mood for an inspirational holiday evening? Look no further than this next pairing. First, watch as Kurt Russell battles blizzards and a shapeshifting alien in the Antarctic (an inspirational feat indeed). Second, watch Russell as hockey coach Herb Brooks lead the 1980 US Olympic hockey team to victory against seemingly insurmountable odds in Miracle. 

3.) A Christmas Story / Elf

Balance out the light, whimsical fun of Elf with the classic, dark comedy A Christmas Story. Watch A Christmas Story first and take note of young lead actor Peter Billingsley. Then, keep an eye out for those same baby blues in Peter Billingsley’s Elf cameo!

2.) Little Women / Edward Scissorhands

Winona Ryder in two of her best films . . . what more could you ask for? Batman maybe? Sure! Watch Christian Bale woo Jo March (Winona Ryder) in the solid 1994 Little Women remake. Pair with Edward Scissorhands and prepare for an enchanted and snow-filled evening!

1.) Die Hard / Love Actually

It may not be a surprise that Die Hard, once again, tops my holiday movie list. Its counterpart on this list, Love Actually, is arguably the best ensemble holiday rom-com made thus far. But, what solidified this pairing as the number one holiday double feature is a fun, dorky character name overlap I happened to notice.

In Die Hard, Alan Rickman plays the unforgettable, ultimate bad guy (with a classical education, mind you), and he’s Hell-bent on enacting his meticulous plan to steal 600 million dollars from the Nakatomi Plaza just before Christmas. In Love Actually, Alan Rickman plays Harry, a father-figure boss at a graphics company. 

In Die Hard, Hans Gruber’s leading henchman is Karl, a massively jacked shaggy blonde haired Nordic (Alexander Godunov). In Love Actually, Harry’s leading designer is also named Karl. With Rickman’s distinct voice, I couldn’t help but enjoy the character name overlap. I’ll always have Hans Gruber’s voice in my head when I hear Rickman utter the name Karl. Try watching both back-to-back and see for yourself! I’ll leave you with quotes from each movie:

Die Hard:
Fritz: (slightly spooked) We have to do something, Hans.
Rickman/Hans: Yes . . . we have to tell Karl his brother is dead. Tell him to come down.
[ . . . later]
Hans: [during a shootout with McClane, who is barefoot] Karl, schieb dem Fenster. 

Hans: [Karl gives Hans a puzzled look. Exasperated, Hans repeats it in English] *Shoot* the glass!

Love Actually:
Rickman/Harry: Tell me, exactly, how long it is that you’ve been working here?

Linney/Sarah: Two years, seven months, three days and, I suppose, what . . . two hours? 

Harry: And, how long have you been in love with Karl, our enigmatic chief designer?

Sarah: Ahm, two years, seven months, three days and, I suppose, an hour and thirty minutes. 

Harry: I thought as much. 

Sarah: Do you think everybody knows? 

Harry: Yes. 

Sarah: Do you think Karl knows? 

Harry: Yes.
Sarah: Oh, that is . . . that is bad news. 

Harry: Well, I just thought maybe the time had come to do something about it. 

Sarah: Like what? 

Harry: Invite him out for a drink and then, after about twenty minutes, casually drop into the conversation the fact that you’d like to marry him and have lots of sex and babies.

Sarah: You know that? 

Harry: Yes, and so does Karl. Think about it, for all our sakes. It’s Christmas. 

Sarah: Certainly. Excellent. Will do. Thanks, boss!