Didn’t they just repaint that for The Cat in the Hat?
One of my favorite movies, The 5000 Fingers of Dr. T, has several scenes in which we see hundreds of little kids, each wearing a “Happy Fingers” beanie with a widow’s peak at the front and a hand sprouting out of the top. Here is the hat. Now imagine a whole flock of kids wearing it ('cuz I couldn’t find a good group photo).
There are a few that got missed in that collage, too. Here’s some links: the “Black Invasion”, the Coruscant Pre-Senate, the Sabe Battle Decoy, and for good measure a better view of the Black Coruscant Post-Senate. I will concede that this hat from the Dune miniseries is pretty snicker-worthy. But if there’s anything in Dune that can beat this “grandfather clock weight/Tibetan prayer wheel” ensemble, I’ll eat my hat.
My system won’t open that link, but some of the Dune hats were, I’ll bet, as bad or worse. Many were ridiculously huge (bigger than the one you post), and you wouldn’t want to be aught out in a wind while wearing one.
The shoe hat has always been one of my favourites.
I love the Dune hats. They fit so well with the scenes.
As for movies that are period movies, out of fashion currently, isn’t the same as bad hats for then.
Princess Ardala from the Buck Rogers pilot movie.
Not as nutty as the Dune or Star Wars hats, but Roz Russell gets mocked for this number in His Girl Friday and later changes into this one.
No one makes out well in The Women. Not Norma Shearer, not the fashion show models and not Roz Russell again.
She was wearing a hat?
Danny Kaye explains where bad hats come from in this clip from “The Secret Life of Walter Mitty.”
MilliCal agrees with **mobo85/B], and says that another episode of The Wizards of Waverly Place features an awful hat that Max had to wear for three days when he first got his powers.
Here’s Crazy Funky Junky Hat on YouTube:
How could we have a thread about funny movie hats and no mention of Hello Dolly!? No production of Hello Dolly! is complete without the crazy hats.
Streisand seemed to be in her fair share of movies with funny hats. Funny Girl and On a Clear Day found her in some interesting chapeaux, as well.
An earlier thread on Alarming Fantasy and SF Headgear has some splendid examples: honourable mention also goes to the mugger with a teatray on his head from The Fifth Element.
The original miniseries DINOTOPIA.
From the film:
Buck Rogers: " … she had the nicest set of…horns at the ball."
Dr. Theophilis: “Yes, it was an attractive hat.”
Great seventies humor… 
What, no love for the Wayan Brothers? How about I’m Gonna Get You Suckas Big Hat Club scenes?
Love, Phil
Dammit! I’ve been searching and searching, and I can’t find the Birdhouse hats from the Other Boleyn Girl. But I swear the Queen and her maids wore upholstered bird houses. Both Mr. singular & I said it out loud when we were watching that.
That’s the one I came here to mention.
You should see his Horton Hears a Who-type shit.