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The Six Movies I MUST Watch to Make it Feel Like Halloween (Especially This Year)

I wasn't a big fan of Halloween growing up. I was a fan of candy and occasionally a fan of dressing up, but I never counted down the days until October 31st. That changed about four years ago. I don't know why, but it did. Now I spend all of September waiting for October 1st and for spooky season to begin. I'm still not so much into dressing up or going to Halloween parties, but I am a huge fan of the aesthetics of fall and the movies. Boy do I love the movies. Freeform's 31 nights of Halloween was like my favorite thing ever on cable. Over the past four years, I have compiled a list of movies that I have to watch during the month of October. If I don't, it doesn't feel like spooky season to me. And this year, with Halloween being basically cancelled, I think these movies are essential for setting the vibe.

Two disclaimers here. The first, I'm a total scared-y cat. I hate horror films. I went to a Halloween movie party one year and there was a movie with a Vampire who jumped out of tree and killed a guy; I couldn't walk under a large tree without my heart pounding for months. So, yeah, this list will not consist of slasher movies or blood curdling horror. It's filled with children's movies and comedies. The second disclaimer is that Hocus Pocus and Beetlejuice will not be making an appearance. Both of these films scarred me as a kid and even though I have seen Hocus Pocus since, they just aren't essential to my Halloween experience. I'm not saying their bad movies, just not for me. I wanted to get that out there before anyone was like "What about Hocus Pocus or Beetlejuice!?"

Ready? Here we go!

  1. Sleepy Hallow (1999)

In this rendition of The Legend of Sleepy Hollow, Ichabod Crane is an investigator with an aversion to blood who has been sent to Sleepy Hollow to investigate a series of murders. All the victims have been decapitated and their heads stolen. Why is this happening? Is there a method to the madness? And is it a town member or the famed ghost the Headless Horseman?

I don't consider myself a squeamish person but oh my goodness does this movie make me squeamish! I don't know what it is about it but sometimes I have to look away from the screen. Because of this, I had never actually watched this movie all the way through. However, that didn't stop it from being a staple in my spooky season. I would try to watch it every year but never succeeded...until this year! And now that I have finally watched it all the way through, here are my thoughts. I think this is the perfect Halloween movie. From the casting to the concept to the weird grey-scale it has, I think it is the perfect movie to keep you a little bit uncomfortable and in the Halloween spirit.

The movie itself is a bit uneven. Sometimes it's good and chilling but other times it can be a bit silly and confusing and the character of the headless horseman can sometimes seem a bit comical. However, I do like how the plot has many twists and turns and you often think you've figured out the mystery only to realize you're wrong. All that aside, I do think this is an excellent movie for getting you in the Halloween spirit (whether you watch it all the way through or not).

2. The Addams Family (1991)

To be honest, this is not my favorite movie but these are my favorite characters. I don't care much for the plot and often get bored with i halfway through, but I could simply not have Halloween season without these iconic characters and the weird things they say. Nor could I go without Christina Ricci as Wednesday Addams. To me (and I think to a lot of us) Christina Ricci is Wednesday. I tried watching the original 1960s television show of The Addams Family and the whole time I was like "no, that's not Wednesday. She's not doing it right!" even though clearly she was the original so if anyone was doing it "right" it would be her. Wednesday is also my go-to Halloween costume because I love her but also because it's so easy. You just pop on a collared dress, throw your hair into some braids, and boom! Festers' your uncle! So, in conclusion, this movie is essential for my Halloween collection almost solely for Wednesday Addams. But also, I wanted to add that Morticia and Gomez are a really strong couple. The family in general, I think, has a really strong dynamic. They all are crazy supportive of each other and the love and pride within the family is palpable. It almost makes this a feel-good family film. Almost. Also, this was the first year I realized Addams was spelled with two Ds.

3. The Adventures of Ichabod and Mr. Toad (1949)

This is a compilation of two short Disney stories combined into one. The first story follows Mr. Toad (the story that inspired the rides at the Disney parks- though the movie is nothing like the story the ride tells) from The Wind in the Willows as he develops motorcar madness. The second, follows Ichabod Crane and his encounter with the Headless Horsemen as told in the book The Legend of Sleepy Hollow. Although the Mr. Toad story has nothing to do with Halloween and indeed takes place partly during Christmas, I still watch it every year. They were produced together and so I feel they should be watched together.

Although this movie includes "Mr. Toad" I think it was clearly meant to be a Halloween movie. It was released in October and as you can see, the cover only shows Ichabod and the Headless Horseman. No J. Thaddeus Toad in sight. I have watched this movie since I was little and therefore it has become an important addition to my Halloween playlist. Some people watch Charlie Brown, I watch Ichabod.

This movie really scared me when I was a kid, but even as an adult I find this to be a fantastic movie for Halloween time because the ambiance and the mood are created so masterfully. Right away we are told that this is going to be a ghost story and are even told that "foreboding" things await in the forest and therefore later in our story. I think that was a great way to start the story because most of the movie is humorous and light-hearted yet we are still slightly on edge because we know something bad is going to happen later. Ichabod's characterization is also very well done. We learn early that he is highly superstitious. This becomes a theme throughout the story and plays a big part in the climax.

Speaking of the characters, I think they play a big part in why this movie gives off such a Halloween feel. What I personally think makes a good Halloween movie is the feeling of unease. I think they should be fun and entertaining but also give you a hesitant feeling. The characters are a big part of creating that feeling because none of them are really likeable. The three main characters are Ichabod, Brom, and Katrina. Brom is clearly the villain as he continuously pranks Ichabod, Katrina is a huge flirt and doesn't really care about the consequences of her actions or the broken hearts she leaves behind, and even Ichabod is questionable. He plays favorites with his students (he's the schoolmaster) based on if their mother is a good cook and basically only loves Katrina because she is beautiful and rich.

However, the most amazing part of this movie is right before Ichabod's encounter with the Headless Horseman. It's Halloween night and Brom has just told Ichabod about the ghost who haunts the forest; lopping off heads to replace his own. The scene where Ichabod enters the forest is so chilling and beautifully done. The clouds form hands that enclose around the full moon, the insects and frogs sound like they are warning Ichabod or calling out his name. This scene is the perfect example of how your brain plays tricks on you when you're scared or alone. I almost hate when the Horseman actually shows up because it diffuses all the tension. Although the arrival of the Horseman may diffuse the tension for a while, it is regained by the end of the movie because it is entirely up to interpretation. The audience is left wondering whether Ichabod made it out of the woods alive or not as well as if the Headless Horseman really exists or was it Brom playing another prank.

4. Mickey's House of Villains (2002)

This is another one I've watched since I was a kid and it has become my own personal tradition to watch it either on Halloween or the day before.

This is a movie based off the TV Series Mickey's House of Mouse. The premise of the TV show was that Mickey has a nightclub where all the Disney characters come to hang out and watch old Disney cartoons. This movie has the same premise, but when the clock strikes midnight and it officially becomes Halloween, the Villains take over the club. The cartoons displayed become scarier and Mickey and his friends are kicked out onto the street. So, the rest of the film is still a series of various Halloween cartoons but with the underlying storyline of Mickey getting his club back from the villains.

My favorite part of the TV show and this film are by far getting to see all the old Disney cartoons. This movie has an incredible range of cartoons from 1937 to 1999 and from haunted houses to Goofy failing as a fairy in a leotard. When I was younger some of the shorts used to scare me but obviously they don't anymore. It's a really cute movie and I watch it now for nostalgia's sake.

"That is all. Brekenridge."

5. Edward Scissorhands (1990)

This is probably my favorite movie on the list and possibly one of my favorite movies ever. However, I only watch it around this time of year which actually works out in my favor because I always forget how amazing it is. It's like a surprise every time.

This movie is about a young "man" who was created by an inventor out of a machine. However, before the inventor could put on the finishing touches (the hands), he died and poor Edward was left with long scissors for hands. Years later, a kind suburban housewife finds him hiding in an abandoned mansion and welcomes him back to her house. Although it does get real serious real quick towards the end, overall I would say this movie is a love story and a comedy.

I think the thing I enjoy the most about this movie is how weird it is. The aesthetics are weird, the characters are weird, the time period is weird. Is it the 1950s? the 80s? And, Johnny Depp is so so good in this film. Edward Scissorhands is so sweet and shy and scared and Johnny Depp portrays that perfectly. I think it's one of the only characters Johnny Depp plays where I don't see glimpses of Jack Sparrow or where I'm not thinking "you're Johnny Depp" the entire time (except for also Willy Wonka. I'm convinced that isn't even Johnny Depp sometimes). This movie is so entertaining yet thought-provoking. In a sense it's showing us that the scariest looking man in the room isn't always the monster. Sometimes the monster is the person we suspect the least. Plus, this is the movie where Winona Ryder and Johnny Depp met so it's like watching a bit of Hollywood pop culture history in the making.

6. The Nightmare Before Christmas (1993)

First of all, I cannot believe this came out in 1993! What!? That was 27 years ago! If you had asked me when this came out, I would have guessed 2005. Anyways, I think by now we are all familiar with the story of how Jack Skellington discovers Christmas and becomes obsessed with being the one to pull it off that year, but with a Halloween twist.

Honestly, this is not a movie I feel I have to watch every year but because The Haunted Mansion at Disneyland is invaded by these characters each year, I feel it is a big part of my Halloween experience. And so, since Disneyland is closed this Halloween, the movie itself has become more important.

More important than the movie is the song "This is Halloween." I add it to my main playlist at the beginning of October and it plays a big part in hyping me up for spooky season.

And there we have it! The six movies I love to watch to get me into the Halloween mood. I noticed a ton of patterns in my movie selections. Two Christina Ricci movies, two Johnny Depp movies, three Tim Burton movies, two movies taken from The Legend of Sleepy Hollow, and four out of the six movies also have something to do with Christmas. And, aside from Ichabod, they were all released relatively in the same time frame. I guess the 90s through the very early 2000s was a good decade for Halloween movies.

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