I have a list of movies to watch every year with every holiday, getting as deep as having a few movies for Labor Day. Since the list of horrible unprecedented things happening in 2020 is growing longer, I thought I would start a year-long series of movies for every holiday. I am really leaning into celebrating the little things this year, as everything around us is horrible.
Since I just decided to do this, we are starting with the nearest holiday that I embrace, which is, of course, my favorite Halloween. Since my normal Halloween activities are largely canceled this year, and I will have no parties to throw or attend, or Trick Or Treaters to hand out candy to, I have decided to forge ahead with my other traditions. This means that the decorating of my home and office have already started, and I thought that I might share my top 10 favorite movies to watch around Halloween.
Some of these are kid-appropriate, and fun for the whole family, but some are definitely not, and I will specify which ones are which. Please be advised some of these are products of their time, and therefore have some less than savory aspects of them, and I will touch on them as best as I can without ruing plot twists. So without any more dithering let's get to the list!
10. The Halloween Tree (1993)
Based on the Ray Bradbury novel of the same title, this movie is fun for the whole family. Kid Appropriate, the story follows a group of friends through time and space to catch their friend Pipkin's soul and to understand the origins of their costumes, and Halloween customs around the world. The Narrator in the film is none other than Ray Bradbury himself, and the mysterious Mr. Moundshroud is voiced by Leonard Nimoy! I will warn you that this film is a product of its time, and not entirely historically or culturally accurate but it is a nice foot in the door for a deeper discussion with your kids or yourself about things like ancient Egypt, and Día de Muertos, and some Celtic history as well.
9. Identity (2003)
This is one of those ones that has some problematic things in it, primarily focused on mental illness, and one in particular but I don't want to spoil the movie so I will leave it at that. Based on the Agatha Christie novel And Then There Were None, this movie centers around 10 strangers who are stranded at a motel in Nevada during a nasty rainstorm. The evening starts off normally enough until they realize they are being picked off one by one by a mysterious killer. It is a great who done it story, and aside from the little bit about mental illnesses and how they are both perceived and treated psychiatrically being a little on the shady side, it's still a great film. A truly wonderful performance from John Cusack as well as a bunch of other stars. This movie has the benefit of having my favorite actress Clea Duvall in it as well. Also this goes without saying, but definitely not kid-appropriate!
8. The Monster Squad (1987)
This title is a classic 80's boy gang story akin to The Goonies and Stand By Me, but with a fun and hokey twist. While the movie did not age as gracefully as one might hope, with a scene that includes the boys peeping on one of the group's older sister, and some less than tasteful remarks about Virginity, it is also really kind of heartwarming and funny. Plenty of potty humor, and quick quotable one-liners, this movie is a gem. Not to mention one of my favorite discussions ever to happen on the screen, about why it is that wolfman wears pants. While The Goonies definitely did better at the box office, this was one of my favorites as a kid, and I would give it a kind-of kid-friendly rating, as it will require some additional discussion regarding consent and such when watching with kids growing up in today's world. Warning this film also deals very briefly with Holocaust survivors, and could be triggering to some viewers.
7. Donnie Darko (2001)
This movie is another one that touches weirdly on mental illnesses and has some pretty graphic violence, I would not recommend this movie to children under the age of 14. I don't want to give too much of the movie away to anyone who hasn't seen it, however, if you like Jake Gyllenhaal, this movie is probably my favorite performance of his. Dark, sardonic, and occasionally fitted with side-splitting humor, this movie is the story of a troubled teen, his dysfunctional family, and a man in a bunny suit named Frank. How that all fits together is often confusing, and I definitely recommend having a couple of views before passing judgment. The movie also features Drew Barrymore as the English teacher we all needed as a high school student. Be prepared to say "what the fuck?" as the movie ends, and start it over. At least that's what I did.
6. Monster House (2006)
Kid-friendly, but if your child is easily scared you might want to take a pass on this one. Without giving too much away, a band of young kids discover that the house across the street is in fact alive. That the old man who lives there is crotchety and mean, but when they are forced to cross into the yard to retrieve a wayward basketball and the old man has a heart attack, they are sent on a grand adventure to defeat the house. I won't give too much away, but it's a great story that boils down to, the only real monster is unkindness, and it endures long after hurtful words turn silent. I personally think this movie is astonishingly well done, and I recommend it to everyone, it really is a very fun movie to watch during Halloween!
5. The Cabin In The Woods (2011)
This is one of my all-time favorite movies, regardless of the season, but it feels so appropriate for Halloween. Five college students decided to take a break from studying and their lives and go to a cabin in the woods, where they get way more than they bargained for. The Author Peter Gallagher claims the movie was based on his self published book, The Little White Trip: A Night in the Pines but it appears the lawsuit for copyright infringement is ongoing. Regardless of whether it was a piece of original fiction or if Joss Wheadon and Drew Goddard ripped off someone else's work, the movie is a delight from start to finish. Dealing with the dynamics of young-adult-centric horror films, and office politics when your job is doing the really hard stuff. The movie gleefully pokes fun at horror tropes, while being super engaging, and fun. Chris Hemsworth, Kristen Connolly, Anna Hutchison, Fran Kranz, and Jesse Williams offer stunning performances as the young people, and there is a surprise Cameo from Sigourney Weaver but I won't tell you when! This movie is graphic, and there is a lot of drinking and pot-smoking, so definitely not kid-friendly. Plus there is a scene where someone makes out with a taxidermied wolf head, so there is always that to look forward to.
4. The Crow (1994)
This one is definitely dated and it shows. Based on a comic book by James O'Barr with the same name, this classic piece of gothic culture is centered on a man, brutally murdered on the night before Halloween, along with his fiancee. His soul is brought back by a crow, and he is immortal and powerful, but only for one night, in order to seek vengeance. The movie has some cheeseball dialogue, and some cringey moments, and some less than inocuous incest, so definitely keep the little ones away. The movie also has some stunningly beautiful imagery and sparked a loyal and undying fan base. The fact that Brandon Lee died on set, also marks the movie as the end of what could have been a wonderful career, he was talented and really leaned into the role as Eric.
I am pretty sure everyone has seen this movie. If by some miracle you have managed to avoid it, then by all means watch away! Kid-friendly and engaging, with a truly fantastic stop-motion animation style this is a favorite. And before anyone asks, yes I do also watch this one for the winter holiday season. The pumpkin king is bored with his life as the end all be all authority on Halloween and takes a weary walk in the woods all night long. He finds himself in a town not made for Halloween, but Christmas! He is delighted and amazed, and decides he is going to bring Christmas back to his town, and take it over from it's reigning king, Santa Claus. Hilarity and mishaps ensue. I think that this film can also be used to start a broader conversation on cultural appropriation if that is your jam.
Another one that I think has taken on a cultural adaptation, but I love it so I included it anyway. In the event that you somehow have avoided seeing this film in the 27 years since it's release (YIKES THAT HURT TO TYPE), it is the story of an angsty young boy and his kid sister who move with their parents from California to Salem. He is a cynic and a non-believer when it comes to spooky stories, and he hates Halloween. In an effort to impress a girl, and fit in after being robbed of his shoes he accidentally wakes up a trio of witches, played by Bette Midler, Sarah Jessica Parker, and Kathy Najimy. Catastrophe ensues, as they battle the trio to save the lives of all the children of Salem, and put the Trio back in the grave. Kid-friendly with a few more adult jokes, it's a delightful film. There are a few curse words to the tune of "damn" and "hell" but used in context, so nothing a little explaining can't help with.
This one is not one for the kids for sure. It is violent and graphic and definitely a slasher film. However, it is one of those movies that pieces together a lot of little stories, and winds them through one really amazing unifying storyline. It's an anthology for sure, but inside of it are a lot of detailed characters with notable back stories, and fully flushed out motivations all wound together into what I consider to be a piece of cinematic mastery. Like all good horror movies, it has it's fair share of camp and humor, but also it's one that I come back to again and again every year, usually watching it several times during the season because I adore it so much. It's kind of like the Scary Stories to Tell in the Dark for grown ups.
Some honorable mentions, of movies that I love but didn't make the list: