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My Top 3: Holiday Movies

11/29/2022

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'Tis the Season for Movie Watching

It's the time of year when it's cold outside, but warm and generally festive inside. The week before Christmas until the new year is holiday-movie-palooza. Here are my three all time favorite holiday movies, and three honorable mentions for your viewing pleasure. 

Die Hard

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When I look back at the movie that I have seen the most times, hands down, over my lifetime, the winner is Die Hard. I first saw it when my sister videotaped it from HBO long, long ago. It has stood the test of time as my favorite movie ever.

The storyline holds together well all these years later. Even the comment in the opening scene (making fists in the carpet with your toes) causes John McClain (Bruce Willis) to end up barefoot throughout the movie. Holly (Bonnie Bedalia) using her maiden name at work prolongs Hans (Alan Rickman) not figuring out her relationship to the rogue cop until near the end. Al Powell(Reginald VelJohnson) and his backstory culminate in him causing a key bad guy's downfall as Sgt Powell overcomes his fears. Everything is tied together.

As an extra added bonus, it's genuinely funny. From Ho-Ho-Ho, to Yippee kay yay, people lacking self awareness (Agent Johnson and Agent Johnson, no relation),  and a few characters that make you want to punch them in the face, this movie has it all--including at little Run DMC and Argyle (De'voreaux White), the best new limo driver a guy could be so lucky as to have on his side.

While You Were Sleeping

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This is one of the best romantic comedies ever made. Sandra Bullock is Lucy, a delightful, but lonely, woman who works for the Chicago Transit Authority. She has a crush on a man she has never talked to who takes the train each day. Heroism and hilarity ensue as she saves her crush, Peter (Peter Gallagher), and his giant wacky family thinks she's his fiance.

Add a coma, an estate furniture business, Peter's brother Jack (Bill Pullman), her landlord's bumbling son Joe Junior (Michael Rispoli) and Lucy trying to come clean and failing, and you have this clever feel-frustrated then feel-good movie.

Throw in a little memory loss, the Callahan family's amazing banter, and neighbor Saul (Jack Warden) trying to help, and you have a movie with the romantic comedy payoff you want after this wild misunderstanding fueled ride.  

When Harry Met Sally

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This movie is not only a classic, but includes at least two Christmas holiday seasons. It's the story of Harry (Billy Crystal) and Sally (Meg Ryan) through their meetings over the years and the changes in their relationship. 

This movie poses big questions. Can men and women be just friends? What is the right amount of cuddling time after sleeping together? Will a man ever leave his wife for his mistress? Can a man tell when a woman is "faking it"? 

This movie's comedic timing is epic. In an early scene, we see Harry having an initial conversation with Sally as he spews diatribes and spits grape seeds out the window. Later, Harry and his best friend Jess (Bruno Kirby) discuss Harry's impending divorce at a football game pausing intermittently to do the wave There's also the amazing scene where Jess and Harry have a phone conversation at the same time as Sally and Marie (Carrie Fischer) and the conversations overlap. All of this is punctuated by interviews of couples explaining their relationships, ending with Harry and Sally telling their story. It's a cinematic wonder. 

Honorable Mentions

With movies, it's hard to pick just three. For good measure, here are three more that I love. 
  • Elf: Will Ferrell as a crazily tall elf named Buddy. Cotton-headed ninny-muggins. Ginormous toilets. Miles Finch. Francisco being fun to say. The inevitable saving of Christmas. You had me at Will Ferrell.
  • White Christmas: Bob (Bing Crosby) and Phil (Danny Kay) as war buddies turned show biz partners. Judy (Vera Ellen) and Betty (Rosemary Clooney) as a musical sister act. Snow.  VistaVision. Choreography. A struggling general. Irrelevant musical numbers for no particular reason. A happy ending that makes me cry a little each time for all the reasons.
  • Bridget Jones Diary: Bridget (Renee Zellweger) and her delightful awkwardness as she decides to change her life. Mark (Colin Firth)'s horrid Christmas sweater. Two British men (Colin Firth and Hugh Grant) attempting to have a knock down, drag out fistfight that hurts a little to watch, but in a hilarious way. Genuinely tiny knickers. It's a lovely triumph of a not-quite-perfect woman who gets the guy she wants more than once.

What About You?

What are your favorite holiday movies? Include them in the comments. 

Learn More

  • 40 Best Christmas Movies of All Time
  • Die Hard
  • While You Were Sleeping
  • When Harry Met Sally
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    Brenda is an innovative learning and development leader, instructional designer, and continuous learner. 

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