7 Most Terrifying Horror Films for Your Halloween Movie Marathon

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This is it. You’ve found it: The one true list of the scariest movies ever made. Every website and blog has compiled a list of frightening films that claims to be a definitive ranking of horror movies during the Halloween season. But they are not it. It is this one. This list. Beware: The following movies are not for the weak, not for the innocent. These are the films one only dares to show at their Halloween movie marathon if they want their guests to tremble with fear for weeks to come.

The Exorcist? The Blair Witch Project? Alien? Halloween? Those movies look like children’s films compared to these truly horrifying, truly unnerving films. They’ll stay with you, crawl into your mind and make themselves at home, never letting you forget what you’ve just seen.

DON’T SAY I DIDN’T WARN YOU!!!!! Keep reading, only if you dare.


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7. I Now Pronounce You Chuck and Larry

Kevin James and Adam Sandler pretend to be gay in order to get a better life insurance policy. That is 100% more unsettling than any dystopian movie I’ve ever seen.

6. Little Nicky

This movie is about Satan and his three sons, and yet the scariest part is not the devil himself but the extremely bad jokes. I wish I could go back in time and save Patricia Arquette and Reese Witherspoon from this hellish movie. Actual hell sounds better than watching Little Nicky.

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5. Just Go With It

The premise of this horror movie pretending to be a rom com is that Adam Sandler’s character lies to women in order to get them to sleep with him. What did Jennifer Aniston and Nicole Kidman do to deserve partaking in such horror?

4. That’s My Boy

Misogyny. Racism. Homophobia. Body-shaming. Those four terrifying things converge to form the beast that is That’s My Boy. Do not watch this movie unless you wanted to be haunted for the rest of your life.

3. Jack And Jill

Adam Sandler plays Jack and Jack’s twin sister Jill. That sentence alone should terrify and upset you to the point of nausea.

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2. Blended

As if the mere premise of getting trapped at a resort for families after a blind date with Adam Sandler were not enough to scare you, the unabashed racism and stereotypical (not to mention monolithic and anachronistic) depiction of Africa is what makes Blended a horror movie disguised as a romantic comedy. Do you ever get indescribably sad about how many movies Drew Barrymore and Adam Sandler have done together? The only way to wipe Blended from your memory and cleanse your soul is to watch Whip It 75 times in a row.

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1. 50 First Dates

This is it: The scariest movie ever made. Imagine Adam Sandler mansplaining your life to you every day. Imagine waking up, not knowing you’re pregnant, and then Adam Sandler informing you that you are pregnant and that he is the father. As with most of Adam Sandler’s horror films, there’s also some casual racism at play. I wish I had the fictitious condition that causes Drew Barrymore’s memory loss in the movie just so I could forget ever seeing it. 50 First Dates will haunt me to my grave.

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Kayla Kumari Upadhyaya

Kayla Kumari Upadhyaya is the managing editor of Autostraddle and a lesbian writer of essays, short stories, and pop culture criticism living in Orlando. She is the assistant managing editor of TriQuarterly, and her short stories appear or are forthcoming in McSweeney's Quarterly Concern, Joyland, Catapult, The Offing, and more. Some of her pop culture writing can be found at The A.V. Club, Vulture, The Cut, and others. You can follow her on Twitter or Instagram and learn more about her work on her website.

Kayla has written 840 articles for us.

21 Comments

  1. Back in college I once bought a pirated copy of 50 First Dates, but my computer couldn’t recognize the CD so I ended up never watching the movie. To think that all these years later I would be feeling so #blessed!

    It still pains me to think of Winona having to act like she could ever fall for that schmuck.

  2. When I was 13 I endured a 27hr bus trip to Germany with my school where our only entertainment was four Adam Sandler films. That journey haunts me to this day.

  3. I wish Adam Sandler had stopped making movies after Happy Gilmore so we could remember him as a quirky one-hit wonder who got quirkily punched by Bob Barker instead of being literally haunted by him forever.

    • I would agree, but I did like Punch Drunk Love(yes it’s a Paul Thomas Anderson film, but he stared in it). Also, as a Jew I am bit partial to 8 Crazy Nights.

      Side note, never thought of 50 First Dates that way.

  4. You know what’s also terrifying? Rob Schneider is probably in every single one of those movies

    • I think he is all of them but Blended. Instead we get the awful Nick Swardson(I don’t how he became a thing for a while). Then again Rob hasn’t really done any good movies himself, which is a shame because how often do you see half Asian half Jewish person in the media?

  5. As bad as 50 First Dates is, That’s My Boy takes the cake for me. Especially the pedophilia that’s framed as “high five bro!” because a 12-year-old boy impregnates his teacher. She does go to jail for it, but it’s still presented as acceptable because she’s super hot. There’s also a baffling subplot that involves a brother and sister in an incestuous relationship. Again, it’s acceptable because they’re both hot. So disgusting I can’t even take it.

  6. I imagine a similar list with Jack Black is forthcoming? Shallow Hal is the worst goddamn movie to ever be created.

    • Oh my God, that movie was on cable this weekend and I had forgotten how hateful it really is.

  7. I’m scared just by looking at this list.

    Also I think he looks exactly like Larry on OITNB (I thought he was him for at least five episodes.. the writers really wanted us to hate him).

  8. Thankfully, I’ve never seen any of these movies. I just can’t do realistic horror like that. I can handle the paranormal, but men like these Adam Sandler characters are real, and they’re out there right now with beliefs and thoughts. Ugh, I just gave myself the chills.

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