Tim Burton has been directing officially since he was 13 years old when he put out the 1971 film The Island Of Doctor Agor. It was a home made looking super 8 movie that eventually made it into Tim Burton's resume as his success grew. He got his first real chance at directing in 1985, at the age of only 27, when he directed the comedy hit Pee Wee's Big Adventure. From there he went on to create such visual and eclectic classics as Beetlejuice, Batman, and Mars Attacks!. In 1990 Tim Burton hooked up with actor Johnny Depp for the classic hit movie Edward Scissorhands and it would not be the last time the two would get together to make one of Burton's visual masterpieces. They got together again in 1994 for the Oscar winning movie Ed Wood which was a tribute to someone that Tim Burton obviously draws a lot of inspiration from, bad movie director Edward D Wood Jr. But Ed Wood was a financial failure despite winning Oscars and many people wondered if Depp and Burton would work together again any time soon. Their answer came in 1999 when Johnny Depp and Tim Burton got together to make yet another Oscar winning movie Sleepy Hollow. The difference this time around was that this Oscar winner was also a winner at the box office as well.

Tim Burton took to telling the story of Sleepy Hollow very well considering that he started his career as an animator for the Walt Disney Company and he wanted to use the 1958 Disney cartoon version of Sleepy Hollow as his inspiration for the look and feel of his movie. There were a lot of differences between the Sleepy Hollow cartoon and the Sleepy Hollow movie. Johnny Depp plays Ichabod Crane in Sleepy Hollow and traditionally, as the story goes, Ichabod Crane is supposed to be an ugly man with many unappealing personality traits. Johnny Depp insisted that he should wear some sort of make up to make him look ugly as Ichabod Crane was supposed to look but Burton insisted that Depp needed to display the ugly parts of Crane's character as opposed to any physically ugly traits and Depp went with it. In the original Sleepy Hollow story the Headless Horseman cannot cross the covered bridge into town and that is supposed to be the safety zone for anyone getting chased by him. But in the Tim Burton version of Sleepy Hollow the Horseman can roam freely across the bridge as he sees fit. It was a little confusing for some people that only had the original stories to go by but Burton and Depp definitely make it work.

The entire town of Sleepy Hollow was built as a set and it was the largest set ever built in England. When the movie was done filming the entire town was dismantled and the land left as it was before they got there. The woods in which the action takes place was all built on a soundstage so that everything from the weather and the elements to the lighting could be completely controlled. It was a massive undertaking that paid off in the end as Sleepy Hollow received three Oscar nominations of which it won one Oscar. All of that and Tim Burton still got to tribute the 1958 cartoon by having Johnny Depp ride his horse while sitting on it backwards just as Ichabod Crane did in the cartoon.