My Top 15 Winter Holiday Movies

Happy Holiday viewing to you, my friends! This list is a mix of well-known standards and a few that I think get overlooked. I'm a fan of stories that use complex relationships to challenge biases, make us laugh at ourselves, and inspires us to be better...or at least believe we can.

15. Home Alone (comedy/family 1990 PG 1h 43m)

why I love it: Iconic. Classic. Hijinks. When 8-yr-old Kevin (Macaulay Culkin) is accidentally left home alone while his family goes on a Paris vacation, he must take care of himself and protect the family home from two con men (Joe Pesci, Daniel Stern) who try to rob the house.

14. Diehard (action/thriller, 1988 R 2h 12m)

why I love it: It's part bad guys, part cop buddy story, part Christmas, and all smart-ass. The original poster was just a building because no one took sarcastic TV actor Bruce Willis seriously (yet) as an action star. After all, action stars were all muscle and grit (think Schwarzenegger and Stallone), but after its box office success, the action genre was FOREVER changed for the better.

13. The Long Kiss Goodnight (action/mystery, 1996 R 2h)

why I love it: Before there was Jason Bourne, there was Samantha Caine. Is that really Geena Davis (Thelma and Louise, Beetlejuice, A League of Their Own) with scary assassin knife skills and amnesia about where she got those skills? Yes, yes it is. My favorite line is when Mitch (Samuel L Jackson) says, "You used to be like, oh phooey I burnt the muffins." 

12. Prancer (Fantasy/Family, 1989 PG 1h 43m)

why I love it: It's one of those "if you just believe" movies, but I still love it anyway. Maybe it's the small town-ness, or the financial struggles of the widowed dad (Sam Elliott). It's definitely the adorably off-key little Jessica (Rebecca Harrell Tickell), and the odd neighbor (Cloris Leachman). 

11. What's Cooking? (drama/comedy, 2000 PG-13 1h 49m)

why I love it: It's an emotional, multi-generational story of four L.A. families of different ethnic backgrounds (Latinx, Vietnamese, Jewish, and Black) gathering together for their Thanksgiving dinners, which vary in food, tradition, and beliefs. The incredible cast includes: Mercedes Ruehl, A. Martinez, Joan Chen, Lainie Kazan, Kyra Sedgwick, Julianna Marguiles, Alfre Woodward, Dennis Haysbert, and many others.

10. The Santa Clause (comedy/family, 1994 PG 1h 47m)

why I love it: I love how Scott Calvin (Tim Allen) resists turning into Santa. I love the depiction of the North Pole. I love the goofy stepdad Neil (Judge Reinhold) and his ugly sweaters. It's cute, it's funny, and it's magical.

9. The Holiday (romance/comedy, 2006 PG-13 2h 18m)

why I love it: I love the concept--a riff on everyone wants what they don't have. Two women (Cameron Diaz, Kate Winslet) swap homes for Christmas, one in sunny L.A. and one in snowy England. It's about finding what's missing and realizing what isn't. They each find love (Jude Law, Jack Black) when they aren't looking. 

8. Pee-wee's Big Holiday (comedy/adventure, 2016 PG 1h 29m)

why I love it: Of course, the original Pee-Wee's Big Adventure forever holds a special place in my heart, but this one is on the list for the SCREAM and the helium balloon scene. That's all I'm going to tell you. When you hear, you'll know. And, yes, I realize this has nothing to do with any December holidays. I just included it because of the title. LOL

7. Holiday Affair (romance, comedy, 1949 NR 1h 27m)

why I love it: Who can resist a widow (Janet Leigh) with a cute little son, Timmy (Gordon Gebert) falling for a witty and handsome store clerk Steve (Robert Mitchum), despite being engaged to reliable attorney Carl (Wendell Corey)? Bonus points for the funny "I like my pajamas big" moment and the scene where she has to vouch for Steve not being a mugger in Central Park, much to the confused amusement of Carl and a police lieutenant (Harry Morgan).

6. Miracle on 34th Street (comedy/drama, 1947 NR 1h 41m / 1994 PG 1h 54m)

why I love it: Some people debate which version of this story is better, the original or the remake, but I like them both. They're both cast beautifully and deliver the "if you only believe in Santa" theme well. I like both the Santas, both of the mothers and their love interests, and both of the little girls. Warm fuzzies, holiday magic, and romance. Perfection.

5. Planes, Trains, and Automobiles (comedy, 1987 R 1h 33m)

why I love it: Two of my all time favorite comedic actors, Steve Martin and John Candy, crack me up from start to finish in this buddy/road trip flick that's really ultimately about finding home. I love when they get pulled over driving the burnt car. Bonus points for the hilarious Edie Mclurg as the airport car rental lady with the best lines ever. Gobble, gobble!

4. Christmas with the Kranks (comedy/family, 2004 PG 1h 34m)

why I love it: There's so much to love! Empty nesters Luther and Nora Krank (Tim Allen, Jamie Lee Curtis) decide to skip Christmas and take a cruise. They refuse to decorate their home or hold their usual party despite increasing demands from friends and neighbors (Dan Aykroyd, M. Emmet Walsh, Felicity Huffman), until their daughter Blair (Julie Gonzalo) announces at the last minute that she's coming home for Christmas. So many quotable lines and hysterical moments that poke fun at the pressures of suburban Christmas. The honey ham scene is the best!

3. ELF (comedy/family, 2003 PG 1h 37m)

why I love it: Director Jon Favreau's vision is so charming, funny, and sweet that this became an instant classic. At the time, few people thought Will Ferrell should play Buddy the Elf, but he is absolutely the only actor who could have pulled this off. Who would've thought James Caan would be a good father, Bob Newhart would be the perfect head elf, or that Ed Asner would be such an excellent Santa? Buddy's a north pole fish out of water, falling in love with Jovie (Zooey Deschanel) and this touching father/son story makes us all believe in Santa. And want to try spaghetti with candy in it. 

2. The Shop Around the Corner (romance/comedy, 1940 NR 1h 37m)

why I love it: This was my Grandma's favorite movie, and I've watched it every Christmas Eve since 1991. It's based on a play, which was set in Budapest. It's got everything I love. Jimmy Stewart, Margaret Sullavan, and a funny supporting cast with classic, quotable lines. If this pen pal love story seems familiar, that's because 90s rom-com YOU'VE GOT MAIL (Tom Hanks, Meg Ryan) is an updated version of it. Sometimes I watch the two films back-to-back for a cozy, "all the feels" evening.

1. When Harry Met Sally (romantic comedy, 1989 R 1h 36m)

why I love it: It has the best lines, the best chemistry, and the best ad lib in the history of rom-coms. When I got my hands on the script, I was amazed to realize that 99% of the lines are not ad libbed by Billy Crystal, even though he seems so natural. That's the beauty of a writer knowing the actors well. However, the best line IS an ad lib from a pro comedic actress. Rob Reiner told his mother Estelle to react when Sally (Meg Ryan) demonstrated a fake orgasm in the diner. She looked at the waitress and said, "I'll have what she's having." I cry at the New Year's scene, every single time.

BONUS MOVIE! Single All The Way (romantic comedy, 2021 PG 1h 41m) 

why I love it: I had to add this one because a dear friend suggested it and I LOVE it. First of all, FINALLY we have a "Hallmark level sappy" LGBTQ holiday rom-com! It's so heartwarming and wholesome, plus JENNIFER COOLIDGE steals the show as the self-absorbed but not self-aware Aunt Sandy. I want to get my hands on this script to find out if her lines were completely scripted or if she ad-libbed a few because OH MY GAWD she had me cracking up. Bonus for Kathy Najimy and Barry Bostwick as the lovable, earnest parents. I've already watched it twice!

Happy viewing,