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Famous Hat-Wearers

Name these people and fictional characters famous for wearing hats.
Quiz by Quizmaster
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Last updated: July 15, 2015
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First submittedJanuary 31, 2013
Times taken11,117
Average score68.2%
Rating4.17
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Clue
Hat
Answer
US President
Stovepipe
Abraham Lincoln
Silent film star
Derby
Charlie Chaplin
He stole from the rich
Green Hat
w/ Feather
Robin Hood
Messenger of the Gods
Winged Cap
Mercury
King of the wild frontier
Coonskin
Davy Crockett
Palestinian revolutionary
Keffiyeh
Yasser Arafat
Movie archaeologist
Fedora
Indiana Jones
Friend of Ginger,
Skipper, and Mary Ann
Sailor Cap
Gilligan
Pop star who also
wore a single glove
Fedora
Michael Jackson
Racially insensitive
cartoon mouse
Sombrero
Speedy Gonzales
Former US first lady
Pillbox
Jackie Kennedy
Clue
Hat
Answer
Dr. Seuss character
Striped Tophat
Cat in the Hat
US President
Panama
Harry Truman
WWI Leader
Spiked Helmet
Kaiser Wilhelm
British detective
Deerstalker
Sherlock Holmes
Religious figure
Crown of
Thorns
Jesus
Hawaii TV detective
Detroit Tigers cap
Magnum P.I.
USA personification
American
Flag Tophat
Uncle Sam
Chicago gangster
Fedora
Al Capone
Friend of Bono
Black beanie
The Edge
Latin American
revolutionary
Beret
Che Guevara
Britney Spears'
ex-boyfriend
Fedora
Justin Timberlake
54 Comments
+2
Level 23
Mar 27, 2013
"Andale, andale! Arriba, arriba!" I forgot what he was called, I could just imagine him :I
+4
Level 27
Mar 27, 2013
It's been ages since I saw Speedy Gonzales the last time. What was racially insensitive about him?
+10
Level 45
Sep 23, 2015
There is absolutely nothing racially insensitive about Speedy Gonzales. Anyone offended by him is just a PC nazi out looking for things to complain about.
+8
Level 93
Apr 20, 2021
One of my favorite stories regarding Speedy Gonzalez is when people tried and succeeded in getting him removed from the show because of his existence being 'insensitive and racist.' He was immediately brought back when the Latino community were overwhelmingly outraged at his being pulled.
+2
Level 79
Apr 20, 2021
I'm actually a great fan of Speedy Gonzales
+1
Level 20
Mar 29, 2013
Could you accept "Christ" for Jesus?
+1
Level ∞
Jul 15, 2015
Okay
+2
Level 32
Apr 2, 2014
I could not get Davy Crockett! I kept getting stuck on Daniel Boone.
+1
Level 51
Sep 22, 2015
i wrote davy jones at first...
+4
Level 55
Sep 23, 2015
Well, my head combined Davy Crockett and Daniel Boone and gave me David Bowie at first....
+3
Level 73
May 10, 2014
A "Derby" hat is known as a Bowler in the rest of the world
+3
Level 84
Jun 19, 2014
Racked my brain trying to come up with the Pakistani revolutionary ... need to read more carefully.
+1
Level 75
Jan 31, 2015
Never kept up with Britney Spears' love life, and had no idea about Bono's friend. Still don't.
+2
Level 86
May 5, 2015
The Edge is the quite famous guitarist of U2...
+1
Level 86
Sep 22, 2015
But you never saw Cher wearing a black beanie, did you?
+1
Level 70
Sep 23, 2015
I think I did, not sure it was on her head though.
+1
Level 58
Feb 20, 2017
I never saw The Edge wear a black beanie, either.
+1
Level 84
Aug 8, 2017
How do his friends address him? "Hey, The!"??? I wonder what they call him for short.
+2
Level 83
Feb 9, 2019
There's a British sitcom Celeb that I enjoyed but others apparently not so much. The title character indeed mentions his pal "The" and it turns out it's The Edge
+3
Level 68
Sep 23, 2015
I kept typing Kevin Federline for Britney Spears but eventually remembered JT. #importantissues
+8
Level 59
Jul 31, 2015
When you enter into Google's browser "president that wore a panama hat." the first 4 out of 5 answers identify Teddy Roosevelt. Truman is not mentioned in any to the 6-7 sites I visited.
+1
Level 61
Sep 22, 2015
Ditto. Only one president is famous for wearing a Panama Hat, and - though he did wear one - it ain't Truman.
+4
Level 75
Sep 22, 2015
I tried Roosevelt first, too, but when that didn't work I just randomly entered 20th century presidents and finally got it. I was surprised when Truman's name worked. He formerly was a haberdasher and wore the proper hat to suit the occasion. One of his favorites was a Stetson. There is a story about a man who saw Truman in a Panama hat and thought it wasn't of good quality so he sent him one of his own. Truman sent the man the hat Truman had been wearing at the time which turned out to be of a much higher quality than the one Truman received. Perhaps that story is the basis of his being thought of as wearing a Panama, but he owned and wore many different types of hats.
+1
Level 57
Sep 22, 2015
Absolutely true.
+1
Level 55
Sep 23, 2015
Yes.
+2
Level 85
Aug 3, 2015
Timberlake is most associated with wearing a trilby (narrow brim), not a fedora.
+2
Level 65
Sep 22, 2015
26% got Truman, shame on you americans
+1
Level 33
Sep 22, 2015
At least more people got Kaiser Wilhelm than The Edge.
+7
Level 57
Sep 22, 2015
Maybe because Truman wasn't actually associated with Panama hats--Teddy Roosevelt was.
+2
Level 84
May 10, 2023
That was my first guess.
+1
Level 84
Aug 8, 2017
Barbara Stanwyck briefly had a Panama hat on in one scene of one movie she made. Maybe she should be on this list too.
+2
Level 55
Sep 22, 2015
I very much enjoyed the irony of typing "Kennedy" as the correct answer into a quiz about famous hat wearers.
+1
Level 51
Sep 22, 2015
you can fez for doctor who...
+1
Level 80
Jun 27, 2019
Yes please!
+2
Level 78
Sep 22, 2015
Should Pharell be added?
+1
Level 70
Sep 23, 2015
Wilhelm and Cat should be enough surely?
+4
Level 24
Sep 23, 2015
Please add Donald Trump. "Make America Great again!"
+4
Level 84
Aug 8, 2017
Without any politics pro or con, Chris makes a good point. That red hat has certainly become iconic enough to make the list. (though it may not be worth it for the flame war it might trigger in the comments)
+3
Level 83
Nov 11, 2015
It should be Spears' not "Spear's"
+1
Level 81
Jan 29, 2021
5 years and counting...
+1
Level 54
Dec 18, 2015
Indiana Jones had more of an akubra
+3
Level 77
Apr 19, 2018
Not a big deal at all, but Britney Spear's is incorrect punctuation
+1
Level 69
May 7, 2019
I thought of magnum, could picture him, but instead if the name, all that came was; mustache mustache, mustache..
+4
Level 57
Nov 7, 2019
Teddy Roosevelt is most famous for the Panama hat, not Truman
+3
Level 90
Oct 6, 2021
Roosevelt was my first guess
+1
Level 93
Nov 25, 2019
I thought the spiked helmet one could be otto von bismarck but as it says WWI leader and he died the previous century, it doesn't fit. Missed that one.
+2
Level 93
Apr 20, 2021
Please change the comment regarding Speedy Gonzalez.
+1
Level 79
Dec 15, 2021
Is Gilligan's Island massive in the US? I've never seen an episode aired in the UK. Am I missing out on something great?
+1
Level 68
Jan 27, 2022
You are absolutely not missing out on anything great. It was, however; fairly big for a brief time period.
+1
Level 78
Nov 29, 2022
Timberlake question is weak...
+4
Level 23
Mar 15, 2023
The Panama Hat is more so associated with 26th President Theodore Roosevelt than it is with Harry S. Truman. Roosevelt wore it to his visit of the Panama Canal in 1906, which then vastly increased its popularity.

No one associates it with Truman.

+1
Level 67
May 12, 2023
please accept Adolf Hitler for Charlie Chaplain, I often get confused between the two
+1
Level 78
Jul 9, 2023
If you're going to put digs into your clues, do it for all of them.
+1
Level 47
Mar 19, 2024
speedy gonzales is not "racist" or "insensitive" or "offensive", stop with the politics.