40. DON JUAN DeMARCO (1995)

As psychiatrist Jack (Marlon Brando) counsels a young man (Depp) under the delusion he’s the womanizer of legend, Jack finds himself so romantically inspired, it repairs his dispassionate marriage with his wife (Faye Dunaway). The charm and talent of the cast carries the movie, but can’t disguise the lack of an interesting story.

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39. CRY-BABY (1990)

It’s not that John Waters’ idea for an ode to teen movies of the ‘50s is a bad one, nor the fact that he makes it a musical. Ultimately, what sinks Cry-Baby is a lack of its own voice. With barely any of Waters’ trademark subversiveness, his throwback musical of a rebel and a bookworm falling in love just feels too much like a flavourless Grease.

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38. NICK OF TIME (1995)

The gimmick of Nick of Time taking place in real-time is entertaining enough, but it’s cinematic junk food. With Christopher Walken at that awkward stage where you couldn’t take him seriously anymore but he wasn’t playing roles for laughs yet, Nick of Time showed Depp was able to anchor painfully mainstream pictures and nothing much else.

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37. THE LONE RANGER (2013)

The controversy over Depp’s casting as the Native American Tonto overshadowed the movie itself, but only because Gore Verbinski’s The Lone Ranger wasn’t a strong enough picture to be heard above the arguing. The final half-hour is absolutely awesome, but it’s not enough to salvage the two hours it takes to get there.

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36. SLOW BURN (1986)

A made-for-television movie, Slow Burn tackled the neo-noir subgenre 20 years before Brick. A detective (Eric Roberts) is hired to track down a man’s missing son (Depp), but soon finds himself unraveling a giant conspiracy. The concept was pretty fresh upon its release, but its execution aches of a TV production.

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35. CHOCOLAT (2000)

Depp reteamed with his What’s Eating Gilbert Grape director Lasse Hallström for this perfectly pleasant tale of decadence and enchantment. Chocolat has moments of vivid life, but also stretches that move so slowly, you wonder if they were filmed on molasses rather than celluloid. Juliette Binoche shines, but Depp can’t quite find the matching tone.

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34. PIRATES OF THE CARIBBEAN:
AT WORLD’S END (2007)

The Pirates of the Caribbean series had diminishing returns through the 2000s, with At World’s End being its lowest point. All the nuances of the first movie are embellished into caricature and the colossal running time leaves the whole bloated affair half-dead in the water.

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33. THE NINTH GATE (1999)

It’s actually surprising it took so long for Depp to team up with Roman Polanski, as both actor and director have a proclivity for creating cinematic unease. Polanski’s dark tale of an unscrupulous rare-book dealer (Depp) hired to verify the authenticity of a tome supposedly written by Satan starts really strongly and only starts to falter about halfway through. Once it does, though, things go badly so quickly, it taints the rest of the film.

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32. ALICE IN WONDERLAND (2010)

One of the least impressive collaborations between Depp and Tim Burton, Alice in Wonderland may be adapted from Lewis Carroll, but instead calls to mind the words of Shakespeare: “Full of sound and fury, signifying nothing.” An all-star cast is wasted (save for the bonkers Helena Bonham Carter as the Red Queen) amidst a numbing bombardment of psychedelic CGI.

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31. INTO THE WOODS (2014)

After Depp’s Oscar-nominated performance in Sweeney Todd: The Demon Barber of Fleet Street, he was lured back to the lyrics of Sondheim by the call of Into the Woods. Unlike Sweeney Todd, which was free to be as morbidly dark as it wished, Into the Woods is clearly a shadow of its Broadway self, with Disney trying to make a family film out of NSFW material. Depp does the best of anyone in trying to keep a subversive edge to his lupine sexual predator.

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ON THE NEXT PAGE: Finding Neverland, Corpse Bride, and Benny & Joon…