Johnny Depp’s Best Movie Predicted All His Worst Performances

Johnny Depp did his best work ever in Tim Burton’s Sleepy Hollow, but it also unlocked all his worst, most cartoonish tics.

By Nathan Kamal
| Published

Before he was one of the world’s biggest box office draws and then one of Hollywood’s most problematic figures and now to the kind of middle place he seems to be in, Johnny Depp was considered an excellent actor. During his recent, notorious defamation trial against his estranged former spouse Amber Heard, Johnny Depp admitted that the massive commercial success of the Pirates of the Caribbean franchise had utterly changed his life and career and it is not difficult to see how. After Captain Jack Sparrow came into the picture, his roles started to get more and more predictable and wacky, relying on costumes and schtick and bizarre characters.

But strangely, Johnny Depp’s best movie actually predicted where his acting style was going to go: 1999’s Sleepy Hollow, in which he played the 18th-century police constable Ichabod Crane. The movie hit the sweet spot between Johnny Depp’s earlier career mostly playing quiet, internally conflicted characters and his following career, in which he battled supernatural monsters and wore a whole bunch of makeup. In many ways, Sleepy Hollow opened a doorway for Johnny Depp to the kind of overacting that would eventually sink to the depths of Dark Shadows and Mortdecai.

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Sleepy Hollow was Johnny Depp and Tim Burton’s third collaboration together, following 1990’s gothic fairytale Edward Scissorhands and the underrated Ed Wood. Technically an adaptation of Washington Irving’s 1820 short story, Sleepy Hollow is more the apex of all of Tim Burton’s spooky influences up till then; it is equal parts 1970s British horror, 1990s bodice-baring sensuality, and Johnny Depp acting like a weirdo. That is not meant as a pejorative, though it might sound like it. 

Simply put, Sleepy Hollow has Johnny Depp in his finest form ever, allowing him to project the emotional vulnerability he displayed so well in What’s Eating Gilbert Grape and Donnie Brasco while still having the bizarre tics of Edward Scissorhands and Fear and Loathing in Las Vegas. It is impossible to overstate just how fun of a movie Sleepy Hollow is, with its proudly artificial soundstages, absurdly gory death scenes, and Christopher Walken as a pointed-tooth undead Hessian warrior. But the movie truly belongs to Ichabod Crane, who the movie delights in proving a cowardly dunderhead every step of the way. 

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Sleepy Hollow cleverly sets up Ichabod Crane as a revolutionary in police methodology, who understandably believes that detectives should use logic and science to solve crime rather than the time-tested techniques of torture and assumption. However, as soon as Johnny Depp gets to the titular town, it turns out that his rationality and belief in forensic technique mean exactly jack squat. A large part of the nasty delight of the film is seeing Crane be absolutely wrong pretty much all the time, even as he holds the superstitious townsfolk in contempt. 

It also helps that Johnny Depp is playing against an ethereally gorgeous Christina Ricci and a collection of world-class character actors like Michael Gambon, Miranda Richardson, Christopher Lee, Ian McDiarmid, and Jeffrey Jones. Ichabod Crane seems just as creeped out by the weirdos of this village as the audience (as well as besotted by Christina Ricci), which just makes it that much funnier as he slowly becomes one of them. Tim Burton and Johnny Depp would never do better work together or find themselves so in sync.

But Ichabod Crane was also a telling sign of where Johnny Depp would go. He is not as cartoonish as Captain Jack Sparrow or Willy Wonka, but his increasingly frantic reactions to the supernatural are the direct ancestors of those characters. He may not be slathered in as much makeup as Barnabas Collins, but the arch costuming and Hot Topic-ready looks of Ichabod Crane were clearly pointing in that direction. Sleepy Hollow is simply the spot where Johnny Depp was just successful enough and on his game to pull this off, but before he took it too far. 

And then, way way too far. Pirates of the Caribbean basically made the Walt Disney Company dump truckloads of money in Johnny Depp’s driveway and asked him to play it to the rafters. With every box office success, he was encouraged to do more, do it bigger. Sleepy Hollow is both the best of it and to blame for a lot of it.