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33

'The Astronaut's Wife'

 
 

This isn't a very dumb hat. Space hats are pretty cool.

 
32

'Platoon'

 
 

War hat. Respect. His face is pretty dumb in it, though.

 
31

'Arizona Dream'

 
 

A baseball cap is perhaps the most subversive of Johnny Depp hats. Plain and unassuming.

 
30

'Edward Scissorhands'

 
 

You would think Edward would not wear a hat. You would think wrong.

 
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29

'Lucky Them'

 
 

Johnny Depp makes a cameo as a friendly neighborhood hobo.

 
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28

'Once Upon a Time in Mexico'

 
 

Displaying surprising restraint.

 
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27

'Fear and Loathing in Las Vegas'

 
 

Well, Hunter S. Thompson also wore some pretty dumb hats. We'll give him that one.

 
26

'Dead Man'

 
 

Existential hat.

 
25

'Benny and Joon'

 
 

Accessories do not give you personality and make inherently charming. Even most 13 year-olds know this.

 
24

'Donnie Brasco'

 
 

Undercover dummy.

 
23

'From Hell'

 
 

This is literally the only scene in which he wears a hat. He couldn't resist.

 
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22

'The Man Who Cried'

 
 

Important historical hat.

 
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21

'Dark Shadows'

 
 

More like Dumb Shadows AM I RIGHT high five

 
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20

'Don Juan DeMarco'

 
 

Early prototype for 'Secret Window.'

 
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19

'The Rum Diary'

 
 

The Wicker Hat.

 
18

'Finding Neverland'

 
 

Pharrell's dumb hat has nothing on Depp. Bonus Dustin Hoffman in a classy hat for comparison.

 
17

'Public Enemies'

 
 

This should be a classic, but it's just proportioned all wrong. It's like he looks at every hat and thinks, "How can I make it bigger and dumber?"

 
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16

'Mortdecai'

 
 

A silly old man's hat, perfect for nightly power-walks or investigating the mystery of who stole the crossword from your Sunday paper.

 
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15

'Secret Window'

 
 

Demented Amish hat or "artistic statement"?

 
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14

'Pirates of the Caribbean'

 
 

Four movies of dumb pirate hat, but at least pirates should wear hats, so we'll go easier on this one.

 
13

'21 Jump Street'

 
 

The first appearance of what has become the classic casual Depp hat.

 
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12

'Benny and Joon'

 
 

This is where he started to believe that dumb hats make him quirky.

 
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11

'The Libertine'

 
 

Spends most of the film without a dumb hat, and then sneaks one up on you.

 
10

'Life's Too Short'

 
 

Dumb hat's too big.

 
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9

'Arizona Dream'

 
 

A proper and dainty hat.

 
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8

'21 Jump Street'

 
 

Undercover acorn.

 
7

'Charlie and the Chocolate Factory'

 
 

The uncanny valley of top hats.

 
6

'The Fast Show'

 
 

Johnny Depp's head went through a Bret Michaels phase after spending a summer watching 'Rock of Love' reruns on VH1.

 
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5

'Jack and Jill'

 
 

It has its own belt to keep it snugly strapped onto his head.

 
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4

'Finding Neverland'

 
 

He found feathers.

 
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3

'Alice in Wonderland'

 
 

Like your grandma's curtains, this thing is so hideous not even the dog will pee on it.

 
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2

'Into the Woods'

 
 

Into the bottom of a mass-produced pimp costume bag from a Halloween store.

 
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1

'The Lone Ranger'

 
 

This one has the high honor of serving a dual purpose: not only is it Johnny Depp's dumbest headwear, but it's offensive.

 
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