20 Essential Movies to Watch In the Holiday Season

Holiday season is here and I am happy to share with everyone 20 essential movies to watch for this Holiday season from me. These are movies that I have watched or rewatched multiple times. Each movie gives you different vibes when you celebrate the holiday with family (Of course there are movies not suitable for children) even though some of them has nothing to do with Christmas. Some are classics, some are today’s movies but together, they give the cheerfulness and the happiness. Grab some popcorn, pour out some wine, sit back, and enjoy.

Always Be My Maybe (2019)

This is the romcom that left me speechless because it is so cute. The story of two childhood friends turned to be lovers. But because of some conflicts, they had to break up. After a few years, they met again and began to work out their left-off relationship. It reminds me that if you were born for each other and fate has settled you to be with other half, then even if the world collides, they will always find each other. In real life, I believe so. Always Be My Maybe is a great way to start off the holiday season.

Where to watch: Netflix

A Christmas Story (1983)

A perfect Christmas movie of childhood. A Christmas Story tells a series of events in a family where a boy named Ralphie tried to convince everyone around why a BB gun was the great Christmas gift. The movie is so cute and so funny because you can watch things from the view of a child. With the narrative of Adult Raphie, it made you feel like how lovely it is when a child doesn't think much about life and just have a spirit of holiday season.

Where to watch: HBO Max

Harry Potter and The Sorcerer’s Stone (2001)

Come on, who doesn't love Harry Potter? Actually, I must include the whole franchise but with me, the first installment gives me the Christmas vibe. Harry and his friends enrolled Hogwart and started to learn magic. They were very excited to be wizards, to belong to each house, and to be friends. That was childhood. It was a Hogwart before You-Know-Who destroyed everything and it was beautiful. We regressed.

Where to watch: HBO Max

The Devil Wears Prada (2006)

If you are struggling with not knowing what to wear for the holiday season, this movie will be the best choice for you. You are invited to the world of fashion and decide what style you want to follow. Each design from The Devil Wears Prada is so fashionable, unique, and luxury. This movie also helps you to change yourself into a different person which can boost your confident. As long as you are willing to be confident, you can do anything in life.

Where to watch: Prime Video

CODA (2021)

I must say this movie is beyond incredible and there is no surprise when it won the Academy Award for Best Picture. CODA gives you a closer look about the deaf. You can understand them more and admire their confidence in life. The story is about a girl who was normal in her deaf family. She loves to sings and wants to pursuit her passion at Berklee College of Music. But she's afraid of abandoning her family when they are facing business trouble. This is a story of family love. Somehow I found CODA can connect or reconnect every family member together and it's precious.

Where to watch: Apple TV+

The Philadelphia Story (1940)

In the Hollywood Golden Age, Katharine Hepburn was a big star and until right now, she is the only person who won 4 Oscars for Best Actress in the Leading Role. I have watched some of her movies and to me, this is the best one. I must say that love is complicated and unexpected in so many ways. Tracy Lord and C.K Dexter broke up and then, they began to realize they were made for each other. I added this movie to the list because first, this is a comedy and we need laugh for the holiday season; and second, we need to have love in life. This will be a perfect movie for old black-and-white fans or couples.

Where to watch: HBO Max

Mariah Carey’s Christmas Special (2020)

This is the only non-movie in this list. As you know, Mariah Carey is like in everywhere during the holiday season. Right after Halloween, you begin to hear All I Want For Christmas Is You. Whether you hate this song or not, you have to admit this song cannot be missed every holiday season. So, in 2020, Mariah Carey had a special show on Apple TV+ featuring many famous Christmas songs as well as special guest stars. The show is a message of hope during the Covid-19 which meant even in the darkest time, the spirit of Christmas will never go away. Mariah Carey always knows how to entertain people.

Where to watch: Apple TV+

Parasite (2019)

If talking about this movie, there will be one word to describe. Magnificent. I must say never in my life I have watched a movie that is perfect in every single detail and I’ve watched 8 times. From acting to directing. From production design to editing. From wonderful screenplay to every metaphor scene. All of those had made the masterpiece “Parasite”. This is not a horror movie. It is drama/comedy. But when you’re watching it, you will never know or predict what’s ahead of you. This movie is about the barrier between the rich and the poor. It seems like each world will never be understood by others. There is one scene in the movie that I like the most. The stair scene. Stairs go up, stairs go down. You should watch it and you’ll understand why I love that scene. Also, the name “Parasite” means to me that in order to survive in this world, each parasite must find its host to hold on, to get the goods from the host. In the movie, I can see that the rich relies on the poor because the rich cannot do things that normal people can do; the poor relies on the rich because the poor needs money. Parasite will be a highlight for your holiday season.

Where to watch: Hulu

Little Women (2019)

Based on the classic by Louisa May Alcott, Little Women told the story of four young women in the March family during the Civil War. Once again, the movie is about family where the sibling love is the center of the movie. The innocence and the taste of first love are so cute and it brings me the vibe of Christmas. I don't know why but it warms my heart. And maybe yours, too.

Where to watch: Showtime

It’s A Wonderful Life (1946)

This movie is considered one of the greatest movies of all time. But at the time it was released, it was a box office bomb and almost brought a film production company into bankruptcy. When I found out this movie for the first time after I watched in my film class at high school, I immediately fell in love with it and I even cried every time I watch it. From that moment, I decided to watch this on every Christmas eve with my family and they love it. The movie is about George Bailey, the most important man at a fictional town named Bedford Falls who had a special impact on every person living there. He wanted to get out of the town and see the world. But he couldn't because there were so many things to take care of and Bedford Fall would be not the same without him. Everyone loved him and yet, in a desperate moment, he lost himself and then realized how wonderful his life was. It's A Wonderful Life is a perfect movie for family and helps you to understand you are important in this life.

Where to watch: Prime Video

Home Alone (1990)

This is another classic Christmas movie. Admit it, we all watched this movie. We all have a good laugh every time we watch this movie. The score of this movie has been trending on TikTok. One boy who was left at home alone after his family forgot him for the vacation trip. At home, Kevin had to deal with two burglars and just like that, a series of funny events happened. Back in the day, Home Alone showed on HBO and other movie channels on every Christmas day. It was like a gift to me. Home Alone definitely is a holiday treat for every family.

Where to watch: Disney+

Elf (2003)

Another Christmas theme movie to watch. I found out there are some movies in this list about family. I mean what is more sacred than family value in the holiday season. Elf is not an exception. It is about a father-and-son love. In this movie, we will watch Buddy, an oversized elf, bonded with his biological father, who seemed very grumpy and lost love in life. Elf, to me, is a healing movie. Besides the laugh, I can see the relationship of Buddy and his dad is so beautiful and so memorable because you will love your dad more and whoever wants to bond with their dad, they can watch this movie together.

Where to watch: HBO Max

A Christmas Story Christmas (2022)

This is the SEQUEL to "A Christmas Story" in 1983. There was "A Christmas Story 2", which was a knife stabbing directly into the fan of "A Christmas Story". This sequel took place when Ralphie has grown up and had a happy family. He was still dreamy, ambitious, and full of enthusiasm. He lived in Chicago with his wife and two cute kids. But after he received a bad news that his dad had passed away days before Christmas, he returned to the town where he grew up and the story of Christmas began. Probably, this sequel is not as good as the original one. But it still has the spirit of Christmas where even in the darkest time, they can still overcome it and bring the cheerful back in order to look into a bright new year. Ralphie has been a good father that his children can look up, a wonderful husband that his wife can rely on, a nice son that his mother can be proud of, and a man that connects everyone in the family together no matter what. "A Christmas Story Christmas" is a great choice to watch for this holiday season when the value of family is put on first.

Where to watch: HBO Max

Breakfast At Tiffany's (1961)

Who doesn't love Audrey Hepburn in her iconic Givenchy black dress with a pearl necklace? Hepburn has portrayed the role of Holly Golightly perfectly that no one else could beat her. Her beauty and elegance in this movie has stolen the heart of so many people including me. The way she talked, she walked, she sang, she dressed, oh my God, inspired me to be more confident in life because Holly didn't mind to show everyone who she really was. "Breakfast At Tiffany's" is a colorful picture of a high class society with all-day parties, money spending without thinking. But there is one thing they missed called "love". Holly desperately chased after the material of rich men but she doesn't feel love in them until she met a writer, Paul Varjak, who was not rich. This movie gives me a hope that true love still exists despite who you are. In this holiday, you can watch "Breakfast At Tiffany's" to feel the love and learn how to host a party for this holiday season. Seriously, no one hosts a party better than Holly Golightly.

Where to watch: Prime Video

Sex And The City (2008)

I know what you think. Why the hell this guy included this movie into this list? This movie is the worst. Well, it doesn't matter if one movie in this list is bad because they are for entertaining. I have been falling in love with "Sex And The City" series and I continue to rewatch every year right after I rewatched "Friends". The movie continues following the life of four best friends, Carrie Bradshaw, Samantha Jones, Miranda Hobbes, and Charlotte York, as they keeps pursuing their lives in New York with sex and love. We will also watching the love of Carrie and Mr. Big in this movie as they got married but with a little twist in it. The reason I chose "Sex And The City" for this list because I think it is like a rollercoaster. It is funny, scary, emotional, and lovable in many different way. To me, it celebrates life and you can also see four women represent each one of us in life. Maybe, when we watch it during last days of the year, we can have a chance to look back at ourselves again.

Where to watch: HBO Max

Psycho (1960)

I have been a big fan of Alfred Hitchcock since the first day I watched this movie in 2014. He was a true Master of Suspense. Exactly like its name, "Psycho" introduced us to Norman Bate, a monster behind the cover of a nice man. And he loved his mommy so much. He would kill any girl who dared to steal his mother's place. Marion Crane was one of those lucky girl. In this holiday season, I want you to watch or rewatch this movie. For those who haven't watched this masterpiece, you will be surprised in a way that you can never expect it to come. It will twist your mind and make you scream "WTF just happened???". It is a little ingredient for this holiday season to spice up and a different from other romance movie. And for those who've watched it before, just enjoy it. It doesn't kill you to watch "Psycho" again, right?

Where to watch: Rent on Prime Video

Chicago (2002)

The holiday season will be nothing if there is no melody. "Chicago" would be the best choice for this holiday season. I want to invite you back to the Golden Age of jazz, where it took the throne, to the age of scandal and fame where they dared do anything to be famous. I believe it's still happening today. The movie follows two girls, Roxanne and Velma, who were both accused of murder and because of that, they became infamous. They wouldn't mind to do anything to take the spotlight until they realized fame never belonged to anyone. It came and went away like wind. The music written for "Chicago" is absolutely fantastic. It will make you keep listening again and again. The melody will never keep you in your seat as well as the choreography. So, let pour some cold Gin and "all that jazz"

Where to watch: HBO Max

Last Holiday (2006)

What if we received the news that we have a terminal illness and we'll die soon, what are you going to do? "Last Holiday" will give you the alternate answer. After Georgia Byrd found out, she decided to withdraw her saving money and spent them for herself. She did all things that she had not done before. Throughout her journey, she met many interesting people who made her remain days in life more wonderful. It is so funny and meaningful. It helped me to realize that life is shorter than what we thought. It's time to take care of ourselves because it deserves to be loved by us more than ever.

Where to watch: Prime Video

Casablanca (1942)

In all the war-romance movie, "Casablanca" will be the best movie that ever made. A love story would be the sweetest thing ever happened during the WWII. The movie is about three people. Rick Blaine, an American owner of nightclub but behind the charming look, he is an American hero who helped Ilsa Lund, his ex-lover and Victor Laszlo, her husband and a rebel being chased by the Nazis. Despite Rick and Ilsa used to have a chemistry and their past, Rick still offered to help her and Victor to get out of the country despite the dangers. I can understand he did that because of love he had for Ilsa. It tells one thing that loving someone doesn't need to be with them. Sometimes, love can be about caring for the person you love and be happy for them as they're in the relationship with someone else. It sounds painful but it is a great gesture. I cried when I watched the scene Rick said goodbye to Ilsa before she got on the plane with her husband. Ilsa asked. "What about us?". Rick said. "We'll always have Paris. We didn't have, we, we lost it until you came to Casablanca. We got it back last night." No matter what happened, Rick would always love Ilsa forever. It is the best choice for every couple for this holiday season.

Where to watch: HBO Max

It Happened One Night (1934)

Let's end this movie list with the oldest film. "It Happened One Night" tells the story of Ellie, a rich girl ran away when her father didn't accept her marriage with the man who he didn't like, met Peter Warne, a journalist, on a bus trip. Like its title, they started to have feeling for each other after just a night but their love was more complicated than that when both didn't know for sure whether their feeling was right or just a feeling. "It Happened One Night" is like the pioneer of romcom genre where funny situations happened in this movie was so random and so ridiculous making this become an iconic movie of all time. Since it is about night and love, I suggest to watch either on Christmas Eve or New Year Eve. And you won't be regret.

Where to watch: Rent on Prime Video