Sleepy Hollow (1999)

There are just director-actor combos that seem to just go together. Alfred Hitchcock had Jimmy Stewart. John Ford and John Wayne. And Tim Burton and Johnny Depp. We’ve talked about their collaborations before with Ed Wood. 1999’s Sleepy Hollow is another one of their perfect pairings. It’s a take on the Washington Irving story The Legend of Sleepy Hollow. Mr. Depp is at his quirky best as a New York City police officer sent to Sleepy Hollow to investigate a series of murders. Christina Ricci is the rich girl who Mr. Depp is drawn to. Mr. Burton has always had a very distinctive visual style, and it’s one most people who don’t pay attention to film study would quickly recognize as a Tim Burton movie. Sleepy Hollow has all that. Its forests and village have a Gotham City character feel. Even though it missed Halloween with its release date by a couple of weeks, it was still a major hit, making more than $100 million. Anytime Mr. Burton and Mr. Depp work together, they seem to bring out the best in each other. Even Dark Shadows, which was not a commercial hit, showcases their chemistry. This is a perfect movie for fall when the leaves have turned, night comes quicker, and there’s an element of the supernatural in the air. Sleepy Hollow is not a straight retelling of The Legend of Sleepy Hollow, and that probably helps it. It turns the expected into the unexpected. Considering how popular horror films are in 2026, Sleepy Hollow’s gothic look feels like it could fit right in with modern movies. Even though there are some people who have let the headlines about Mr. Depp color their view of him, it would be a mistake to overlook Sleepy Hollow because of it. Most of us weren’t alive during Mr. Hitchcock and Mr. Stewart’s box office run. And we sometimes regret missing out on something we had at the time and just didn’t realize it. Don’t let the pairing of Mr. Burton and Mr. Depp be one of those regrets. Hollywood’s flavor of the month capacity may have already passed them by, but you still have a chance to enjoy them right now.

Scream (1996)

Movies still have the power to become cultural events. But it’s not as strong as it used to be before our collective attention span splintered into a trillion directions. It is hard to describe the effect 1996’s Scream had when it was released to someone who hadn’t

Mannequin (1987)

If you can say one thing about 80s cinema, it was willing to take chances. 1987’s Mannequin might have been the most ludicrous concept to come to a theater, until Weekend at Bernie’s two years later. Kim Cattrall is the spirit of an ancient Egyptian who somehow gets

Romancing the Stone (1984)

Hollywood is a copycat factory. If there’s a hit movie, you can guarantee there are going to be movies just like it in the years following its release. Raiders of the Lost Ark set the world on fire in 1981, so of course there were going to be clones.

Sixteen Candles (1984)

There are times movies can represent the generational divide between audiences. 1984’s Sixteen Candles is one of them. Among its core Gen-X audience, it’s considered a classic. However, among Gen-Z on the internet, it’s considered a crime against humanity. John Hughes learned a lesson on

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Scream (1996)

Mannequin (1987)

Romancing the Stone (1984)

Sixteen Candles (1984)