Woody's Hats

This is the place to go for all things hat-themed in the Woody Harrelson universe! Every time Woody wears a hat in one of the movies I watch, I will chronicle and rank it here, along with some in-depth and important commentary. This list is complete as of March 2022!

88.) Battle in Seattle (Police Helmet)

Ugly!

87.) Wildcats (Football Helmet 2)

At least the other one has a yellow face thing!!!!! This one doesn't have anything going for it!!!!!!!

86.) Wildcats (Football Helmet 1)

See above. Also, it doesn't look much like a bike!

85.) Kingpin (Fedora)

I think this hat really works for Woody, color palette-wise. However, this does look like a hat you might come across at Marshalls or TJMaxx, and while I certainly do not consider that an insult, it means it's not very special! Furthermore, I think if I came across a person other than Woody Harrelson wearing this hat in my own life, I wouldn't like it very much.

84.) Lost in London LIVE (Fedora)

I get that this hat is a reference to one of Woody's most famous hats (see above), but it really does not make it any better! Ugly hat!

83.) Palmetto (Straw Hat)

Stop!!!!!!!

82.) Surfer, Dude (Crocheted hat)

This hat sucks, man. Like most crocheted things, it is extremely ugly and very disappointing. Looking at it makes me feel angry, uncomfortable, and upset.

81.) The Messenger (Camouflage Cap)

Boring. Unoriginal. Been done before.

80.) Defendor (Grey Beanie)

Sad. :(

79.) The Thin Red Line (Army Helmet)

It's the texture of this hat that really grinds my gears. I get that probably if you're trying to be sort of camouflaged in the jungle, you might not want a really shiny hat. But shiny is more fun! I think, if you're going to force young men to go off and die in wars, they should at least get to wear a shiny hat. It wouldn't make it worth it, obviously, but it would make it a little better, in my opinion.

78.) Transsiberian (Baseball Cap)

This hat is fun and casual—if it wasn't blue, it would probably be much higher up on this list. As it is, I think it's pretty lame. Why is blue the default color?? There are so many other, better colors out there, and I'm just not sure why this is the one we had to get stuck with! I'm done with blue's tyranny, and I hope you'll join me in taking a stand against it!

77.) Indecent Proposal (Navy Baseball Cap)

Just another sad blue baseball cap!

76.) North Country (Blue Baseball Cap)

Will the tyranny of the navy blue baseball cap ever end?????

75.  L.A. Story (KYOY Blue Baseball Cap)

At least this one appears to be part of work attire so ostensibly Woody had no choice but to wear it.

74.) After the Sunset (FBI Cap)

Dale Cooper would never wear this hat.

73.) The Big White (Black Baseball Cap)

At least it's not blue.

72.) Defendor (Black Headband)

Woody wears this under his Defendor helmet. I think that would have been the perfect place for a wonderful pop of color, but what do I know? At least it looks cozy.

71.) Ted & Venus (Mystery Headwear)

Listen, he's definitely got something on his head. Woody's only in this movie for probably two minutes, and the whole time he's holed up in a little box draped with an American flag. This is about as clear as the image gets, so it's what I'll have to work with. My general rule for whether or not to include a piece of headwear on this list is twofold. I ask myself if the headwear was donned by the Woody purposefully to fulfill a goal oriented towards his own safety, fashion, or function. Hence, a burlap sack placed over his head in Shock and Awe doesn't count, nor does the bag Woody puts on right before blowing his brains out (spoiler!) in Three Billboards. While both of these bags fulfill a function, they're not exactly self-serving. That might not make a lot of sense to you, but it makes a ton of sense to me. No one is reading this anyway, so it only matters what I think. And what I think is that in this scene Woody is wearing some sort of black headband contraption. It's obviously very dirty, but you can't really blame him. It's better, anyhow, than the plethora of blue baseball caps Woody is seen in otherwise.

70.) Battle in Seattle (Black Beanie)

Just an extremely boring black beanie! It doesn't even look that warm, and you can tell from the way Woody's character wears it in the movie that he's only wearing it because he's insecure about his bald head (the character, I mean. I'm pretty sure Woody himself is quite comfortable being bald).

69.) Money Train (Striped Grey Beanie)

Not a huge fan of this one! I love stripes as much as the next guy (probably more, actually), just not these ones! It doesn't fit Woody very well, and what's up with that seam in the back?

68.) Free Jimmy (Forgettable Hat)

I forgot this hat existed as soon as I took a screenshot of it. Maybe because I watched this movie on 2x speed in German with no English subtitles and those weird dots covered the whole screen. Maybe because the hat is highly forgettable. The world may never know.

67.) The Glass Castle (Black Baseball Cap)

I know you all know by now how I feel about a boring, blank baseball cap. They're awful! The only reason this one is so high up on the list is that it's part of a disguise. You have to admit, a baseball cap is one of the best hats for purposes of disguise—it hides your face, and is so boring that no one wants to look at you more than they have to. I think this is a clever use of a basic hat!

66.) Lost in London LIVE (Black Beanie)

God, I just really wish Woody had taken the special opportunity to wear whatever the hell kind of hat he wanted in the movie and run with it, instead of wearing another drab, boring hat. Sad!

65.) Sleepwalking (Mystery Beanie)

For the life of me, I cannot figure out what is depicted on this hat! Some sort of cartoon character? A Phoenix? A Pokemon? I'm just not sure, and for that, this hat can't go any higher on this list, even though I kind of like the color combination.

64.) Wag the Dog (Prison Hat)

Look, I like neon orange as much as the next guy—in fact, probably quite a bit more than the next guy. But I find that neon orange works best in places you wouldn't expect to find it. On a pair of overalls, for example, or a beautiful hand-knit sweater. But when it's somewhere expected, like a dog collar, or a safety vest, or a prisoner's hat—well, it just doesn't do it for me!

63.) The Big White (Balaclava)

A controversial entry, perhaps, seeing as in the past I have neglected to include hoods, burlaps sacks and a certain bag with a note written on it worn over the head. A balaclava is not a hat, per se, but it is a purposeful head-covering which is not part of another garment (ie a hood). As you know, this is my list, so I can include whatever I want, but I thought it would be kind to explain my reasoning to my readers nonetheless. Anyhow, it looks cozy, which is probably a big requirement in the Alaskan chill. PS. I'm calling it a balaclava instead of a ski mask not to be pretentious, but because I think it sounds nicer.

62.) Surfer, Dude (Bandana Headband)

Normally, I'd be excited to see such a fresh hairstyle on Woody. But not this time! His hair is ugly, frizzy, and uncared for, and the bandana does nothing to help. It's way too far down on his forehead, and to top it all off, it's navy blue. Very sad.

61.) Play it To the Bone (Navy Blue Hat)

I'm just not a hue fan of such a folded up hat. It looks funny and short. 

60.) Kingpin (Amish Hat)

Unfortunately, this hat is mostly guilty by association. Woody wears it in a stupid scene in a stupid movie, and therefore I don't like it very much! It's also pretty boring.

59.) Zombieland (Striped Beanie)

This hat gets points for being outside of Woody's regular repertoire. I also really like the colors. However, he's definitely wearing it pulled down way too far over his head (I feel like if we had a front view we wouldn't be able to see his eyebrows), and there's something about a beanie on a bald head that just feels wrong to me.

58.) Sleepwalking (Tan Baseball Cap, Rasta Striped Knit Hat Combo)

Layers? Yes. Elegantly chosen ones? No.

57.) The Grand (Black Cowboy Hat)

In the realm of Woody's many wonderful cowboy hats, this one isn't really anything to write home about. The addition of the eyepatch is the only thing that elevates this look, but it's simply not doing enough.

56.) Defendor (Defendor Helmet)

I really like that this hat lights up. However, I feel like when you're a superhero you can wear whatever kind of hat you want in whatever color you want, which makes the choice of a plain black helmet pretty sad in my opinion.

55.) Now You See Me (Brown (?) Hat)

Brown is a great color! But this is a stupid hat. It has a stupid bow and a stupid shape. Not a big fan.

54.) Zombieland (Cowboy Hat)

This is a pretty good hat. Woody's character definitely picked it out for that authentic zombie hunter look. And you have to respect that. The only thing I don't like about this hat is the weird grommets in the side. They remind me of a zookeeper, and that just throws the whole vibe off.

53.) Management (Pork Pie Hat)

This hat has the potential to rank higher, but the problem is we barely get a chance to see it! It does seem sort of plain, though, so I don't mind putting it here.

52.) Defendor (White and Rainbow Beanie)

I love this hat's beautiful rainbow stripes! It sure has a lot of personality, especially when you take into account the way Woody chooses not to pull it all the way down, leaving the top loose. However, it looks a little dirty, and the white color really shows that off.

51.) The Grand (Straw Cowboy Hat)

Another pretty subpar cowboy hat in my opinion. It reminds me of the hat I wore to the cowboy-themed open mic night my friend and I planned in high school, which is to say it looks cheap and inauthentic. It is, however, well suited to its environment, and it's definitely nicer than the Zombieland hat.

50.) The Prize Winner of Defiance, Ohio (Tan Hat)

Turns out that this type of hat isn't quite so bad when it's being worn in a time when lots of people were probably wearing this kind of hat. No one in the 21st century can wear this hat, but it seems like it was probably okay in the 20th century.

49.) The Big White (Brown Knit Hat)

This hat gets loads of extra points because it is the first hat in this adventure so far which has seemed to be symbolically important to the plot. It starts out as Robin William's hat, but he takes it off and puts it on Woody's head just before Woody is shot. Their characters are brothers, but they have kind of a complicated relationship, so this is what Robin does instead of trying to save Woody from dying, which I guess is nice. It's also a little mean though.

48.) Shock and Awe (Bicycle Helmet)

Safety first!!!

47.) Three Billboards Outside Ebbing, Missouri (Policeman's Hat)

This is a good hat, even if it's not really anything special. It's probably just a standard issue police chief hat, but that rich black is pretty classy, and the silver buckle adds a little bit of pilgrim-inspired pizazz.

46.) Money Train (Black Beanie)

This hat is a staple—reliable, warm, and in a nice neutral so it'll match practically any outfit. It's just a little boring, even though it looks extra cozy.

45.) The Glass Castle (Black Beanie)

Surprise, surprise—another cozy looking black winter hat! At least this one is sideways.

44.) Now You See Me 2 (Grey Hat)

Woody wears this hat in the most iconic scene of Now You See Me 2, and it definitely gets a lot of points just because I associate its sleek neutral tones with that incredible (magical!) moment. Besides that, I think it's nice and understated while also having a bit of magician's flair.

43.) Zombieland: Double Tap (Santa Hat)

This was a big moment for me, obviously. Santa! However, this hat doesn't even begin to exude the potential excellence which is achievable by the perfect Santa hat. You can barely see the red top, which is, to me, one of the most important elements of a great Santa hat. 

42.) North Country (Maroon Baseball Cap)

I mean, it's pretty obvious to me that the costume designer for this movie simply went to the nearest blank baseball cap emporium and bought a couple blank hats to see which ones would go with which of Woody's character's outfits. They didn't even bother to rough them up or make them look used at all, which is kind of annoying, and I really don't think I've ever seen anyone normal wear just a blank baseball cap! Slap a patch on there, for God's sake! Nonetheless, I have to be thankful that this hat is not navy blue. The color doesn't look so great in this picture, but it coordinated well with Woody's outfits, and at this point and pop of deep maroon is enough to satisfy me.  

41.) Edtv (Black Hat)

This isn't the first time Woody's worn a nondescript black knit hat. It is, however, the first time he's chosen to pair such a basic piece with such a dazzling pair red of sunglasses! Very recently, I learned the term "successorize." As you might be able to deduce, the word is a portmanteau of the words "success" and "accessorize" which, when applied to an outfit, means a person has done quite a fine job of picking out the outfit's supporting elements. That's exactly what's gone on here, and the results, I think, are just thrilling.

40.) The Hi-Lo Country

It's too bad that Woody's best cowboy movie features the cowboy hat that I am have the least opinions on. Fine hat. Nothing special. Nothing bad.

39.) Sleepwalking (Tan Baseball Cap, Red Knit Hat Combo)

You all know that I love a layered look! This one is pretty nice.

38.) Bay Cove (Baseball Cap)

I painted my bedroom this color in January. I think it's nice.

37.) Indecent Proposal (Wedding Hat)

Generally, I think a hat is a pretty fun choice for a wedding! However, there are definitely specific hats that would be more fun for a wedding than this one. It does have pretty good vibes, though! I like the slightly disheveled look—slightly fanciful without being too formal.

36.) The Glass Castle (Yellow Construction Helmet)

If you keep scrolling, you'll find another construction helmet further down this list, ranking much higher. They're essentially the same helmet, but this one is way too clean and shiny. It's never seen a day of honest work in its life! Without marks of wear, how are we to know that this helmet will actually keep anyone safe?

35.) Friends With Benefits (Periwinkle Headband)

You may have heard that I hate the color blue—and I do! I think it's awful, with just one exception: periwinkle. Besides having a very fun name, I think this hue is rather nice looking, even if it's a part of the blue family. Not only is this bandana-headband periwinkle, it's very suited to the occasion it's being worn at (a casual outdoor basketball game) while still maintaining a sense of fun! Furthermore, Woody's character pairs it with a bright sunshiny yellow tank top, and this headband really makes that pop. There's nothing quite like the power of complementary colors!

34.) The People vs. Larry Flynt (Army Helmet)

Obviously this isn't really a spectacular hat in and of itself, but the attitude with which it is worn makes up for a lot of that.

33.) The Highwaymen (Grey Cowboy Hat)

This is a pretty boring hat, but it's a classic shape, and you have to respect that.

32.) The People vs. Larry Flynt (Visor)

We love a good visor, don't we, folks?

31.) 2012 (Mystery Hat)

I have no idea what type of hat this is, but I really respect it. It's so different from what we usually see Woody in, and on top of that, it's pretty different from what you'd expect a radio host/prophet to be wearing. I really like the subtle contrast of colors, as well as the beautiful applique design around the rim. I believe I'm also detecting a bit of iridescence at the top, in the greenish fabric that's striped with red, and we must celebrate iridescence whenever we get the chance. I'd love to get a closer look at this hat, just so I could get to know it a little better, but even without doing so, I know it's an excellent and unique hat deserving of acclaim.

30.) Transsiberian (Ushanka)

This is SUCH a step up from a regular old boring winter hat! The earflaps give it so much personality! I wish it were fur-lined, like an authentic Ushanka, but I think that could be a little pretentious, especially for a humble Iowan Christian, like Woody's character in Transsiberian. That it's baseball cap inspired makes it less authentic Russian-wise, but more authentic Woody's-character-wise, and I think that's sweet.

29.) Now You See Me & Now You See Me 2 (Magician's Hat)

You can call me a purist, but I really think a magician's performance hat should be a top hat! No rounded edges, no weird bumps—I'm talking full Abraham Lincoln. Obviously, this hat doesn't quite fulfill these requirements, rather serving as a subtle reference to the classic shape we associate with magicians. I get it—Woody's a modern guy, and he likes to spice things up a little bit. I'll let this one slide.

28.) Shock and Awe (Beret)

We're only granted the quickest of glances of this hat, for Woody takes it off almost immediately in order to play some tunes on his guitar. But from what I can tell, this is some sort of green woolen military beret, which is a style of hat I quite like! But I can't be sure!

27.) Wilson (Prison Hat)

This black beanie ranks higher than every other black beanie on this list due to the very good vibes of this particular scene, which is the Paddington 2/Crime and Punishment crossover of my dreams. We can only pray that Woody will be cast in the recently announced Paddington 3. 

26.) Money Train (Pork Pie Hat (?))

At least, I think it's a pork pie hat. I sure am learning a lot about hat types! This feels like a classic to me, and it looks especially great with the long coat Woody's character wears in this scene. If I was at a thrift store and I saw this hat, I'd definitely put it on jokingly but then kind of like the way it looked but ultimately decide that I would not get enough wear out of it to justify the purchase. 

25.) Scorched (Camo Bucket Hat)

It probably won't come as a surprise to you that I'm a little peeved that bucket hats are so In lately. Objectively I think they're a wonderful type of hat, but when you can get them a dime a dozen at Urban Outfitters, they lose a lot of their appeal. Ever since I learned the difference between hats and caps, I'm always on the lookout to identify the difference, and in my studies I've noticed that caps are WAYYY more prevalent than hats, at least in my parts. That's kind of ironic, since I think most people would tell you that hats are more common than caps (this is, I think, generally an issue of baseball cap misidentification). Anyway, when you do see a hat, it's pretty exciting. More often than not, it's a bucket hat. So at the same time, you're excited for having spotted a real hat out in the wild, but you're also disappointed that it's such a trendy hat, and therefore not a truly unique fashion choice. In the context of Scorched, I think this is the perfect hat for Woody's character, since he's sort of a desert cowboy zoologist, and a camo bucket hat is definitely the kind of hat a desert cowboy zoologist would wear. If bucket hats weren't so trendy, I'd probably like to wear this hat. 

24.) Sleepwalking (Orange Baseball Cap, Red Knit Hat Combo)

It's sort of amazing, isn't it, how two not-at-all extra-ordinary hats can come together to create something magical? Woody wears quite a few layered hat looks throughout this movie, but this is far and away the best one—the orange pairs beautifully with the red to create something bold and fresh.

23.) Solo: A Star Wars Story (Disguise Hat #1)

Sci-fi chic! Great hat and goggles combo.

22.) Mother Goose's Rock-n-Rhyme (Sheep's Bowler Hat)

I don't really think an explanation is necessary for this one.

21.) Now You See Me (Straw Hat)

At first glance, this hat may appear similar to the dreaded hat from Kingpin. On the contrary, however, it's much flatter and has a much more old fashioned feel! I like the brown ribbon, and generally this hat reminds me of Bert from Mary Poppins, which is pleasant! Even though this isn't really my favorite style of hat, I would enjoy seeing Woody dance with a bunch of penguins.

20.) Cool Blue (Party Hat)

What can I say? I love a festive look!

19.) Money Train (Backwards Flat Cap)

I had to do some research to figure out what to call this hat—I wasn't sure if it was called something different if worn backwards. I didn't really find an answer to that, but I did find this great tidbit, about the difference between a hat and a cap: hats have brims that go all the way around, while caps only have partial brims! According to these rules, I better be very careful when labelling Woody's hats in the future. On to the hat itself, though—I think this is a reasonably good hat. It's a classic neutral, and appears to be made out of a nice woolen material. If Woody was wearing it with the brim in the front, it would not be so high up on this list. But backwards, I think it has a little something special.

18.) The Duel (Gray and White Cowboy Hat)

This hat is pretty good. I like the intense contrast of colors, and it's a classic shape. There's nothing really special about it, though.

17.) Palmetto (Noir Hat)

Only a few types of hats have specific genres attached to them, so it's exciting to see good old film noir hat on our friend Woody—I might not have known what kind of movie this was without this hat to tip me off!

16.) Now You See Me 2 (Pizza Delivery Baseball Cap)

I like how it just says "Pizza".

15.) Solo: A Star Wars Story (Disguise Hat #2)

It's just so practical!

14.) Austin Powers: The Spy Who Shagged Me (Velvet Beret)

This hat continues what is becoming a grand tradition in the world of Woody's Hats, where the hats from the movies I like the least often rank quite high on this list. I'm not sure what that says about my taste in hats, but no matter. The thing I love most about this hat is the beautiful velvet material from which it is crafted. It looks extremely soft, and I quite like the color, too. I'm not really sure why Woody is wearing this particular hat in the movie, where he's appearing as himself, but I can only assume that it's because Woody himself may have been known to wear such hats on his own time, which I find quite interesting indeed.

13.) Zombieland: Double Tap (Cowboy Hat)

This hat is the ONLY part of the second Zombieland movie which is better than the first. Clearly, in the years which passed between the two films, Woody's character saw how important it is for a zombie killer to have a great hat. And this hat is great! Although that shade of teal is definitely not my favorite color—not by any means—I appreciate a good pop of color as much as the next guy! And against this darkest of blacks? It's a powerful statement, that's for sure. Well done indeed!

12.) No Country For Old Men (Cowboy Hat)

I think you'd be pretty hard-pressed to find a person who doesn't agree that the cowboy hat is a hat made for Woody Harrelson. Lots of people would look really dumb in a cowboy hat this big, but when he walked on camera wearing this bad boy, I cheered. And check out that braided band! Really nice!

11.) Defendor (Construction Helmet)

What is not to love about this wonderful helmet?! It's safe, vibrant, and certainly an attention grabber!

10.) The Cowboy Way (Cowboy Hat)

Love the red accent and the dramatic flair of this authentic cowboy hat!

9.) The Messenger (Black Beret)

Even though this is a standard-issue army uniform hat, I won't hide my feelings for it! It's fabulous, and has a ton of personality. I noticed that unlike the other character in this movie, Woody's character wore his a little askew, which is a classic Woody move! Wearing this hat a little off to the side definitely made it more jaunty AND more interesting. Without the little turquoise insignia on this hat, I would wear this hat myself, which is a first for this list! 

8.) LBJ (LBJ hat)

WE MUST RETURN TO AN ERA WHEN PRESIDENTS WEAR HATS.

7.) Bay Cove (Scary Hat)

Great hat, greater presentation.

6.) The Prize Winner of Defiance, Ohio (Feather Hat)

I've just invented a new category of hats. They're called "gaspers," and they are, as you may guess, hats that make me gasp when they come up on screen as I frantically fumble to screenshot them. This hat is a top-tier gasper! The feather is the perfect accent to the sleek black base. There's nothing I would change about this hat!

5.) A Prairie Home Companion (Big Brown Cowboy Hat)

Woody wears a lot of cowboy-inspired hats, but this is the first one that really made me believe he was a cowboy. It's huge, first of all, which everyone knows is a key component of a cowboy hat. It's also a beautiful brown color, which is so much better than either black or tan, at least when we're talking cowboy hats. It's simple, too—no extra frills on this baby! In my opinion, this is the perfect cowboy hat.

4.) The People vs. Larry Flynt (Tricorn Hat)

Now THIS is a hat!!!!!

3.) White Men Can't Jump (Tie-Dye Baseball Cap)

Yes!!!!

2.) Midway (Army Cap)

Wow! What a hat! If I was strolling around an antique shop and caught a glimpse of this hat, I would gasp and run to its side at once in order to try it on. If it was below forty dollars, I'd probably even buy it! I mean, how could I say no to a hat like this? The gold appointments are astonishing in their beauty and grandeur, but the tan is enough to still make this hat feel like a neutral! I think I could wear this with practically any outfit, and it would add exactly the amount of pizazz with a vintage twist that I'm always striving for. I want this hat!!!!

1.) The Duel (White Mayor's Hat)

Wow, is this an incredible hat! I truly gasped when it came on screen. It's the classic mayor's hat, but with a twist! I've never seen a white top hat before, and I doubt I'll ever see one again. I think the subtle contrast of the satin ribbon gives this hat a sense of luxury—maybe even opulence—while still remaining humble and relatively unimposing. This hat is strong and sturdy (as it should be, for life in the Wild West), but maintains a sense of whimsy, which is so incredibly important in hats if you ask me.