Theatrical:

10. "Spooks", Oswald Rabbit cartoon, 'Phantom of the Opera' parody. "Hell Heels" is close thouh...

9. "Great Piggy Bank Robbery", Daffy Duck as 'Duck Twacy'. Upclose scenes of the villians.

8. "Stage Hoax", early 50's Woody Woodpecker cartoon. One scene features Woody in drag and with multiple legs (don't ask)

7. "Alice In Wonderland", several scenes especially towards the end with the chase.

6. "Duck Amuck", Daffy Duck cartoon where an unseen animator (a certain wabbit) constantly changes the scene and even Daffy's body


5. "Der Fuehrer's Face", WWII Donald Duck cartoon featuring the duck being forced to work at a munitions factory for the evil dictator


4. "Minnie The Moocher", most Betty Boop cartoons would fit the category, though it's the strangest I've seen. About Betty & Bimbo going to a cave and meets a ghost walrus voiced by Cab Calloway

3. "Sh-h-h-h-h-h", last Tex Avery directed short about a man that wants complete silence

2. Bugs Bunny invading Elmer Fudd's dream in "Big Snooze"

1. Pink elephants scene from "Dumbo"


TV cartoons:

"Traffic Zone" 4 part episode of "Hoppity Hooper" with the main characters visit another dimension that turns people into vegetables (like the bear turining into a turnip).  A bit strange...

"The Simpsons"... when Homer & Bart turns CGI in a early '90's Holloween episode. Good thing the movie wasn't done that way...

"Ren & Stimpy"... "Black Hole" when the main characters constantly mutate would be the weirdest... though the show's plain twisted in the first place (in a good way)

"South Park"... many  episodes  including the first with an alien probe inside of Cartman and parts when he sings "I Love To Singa"

That's a pretty good list. I'll have to think of some of the weirdest cartoons I've seen here in alittle bit.

TV:(From what I seen while at relatives, I don't have cable at home)

1. Squidbillies- In general.

2. Aqua Teen Hunger Force- I've watched a few of these, one of the weirdest was the one where Meatwad had the Ouija-board video game(for lack of a better word).

3. Cat-Dog- In general.

4. Cow & Chicken- Especially when Cow becomes Super Cow.

I can't think of any theatrical at the moment, I come back later.

Uh Family Guy I dont understand it at all.. but its addictive.

The Ambigeously Gay Duo from SNL

Hmmm....

1. Catdog
2. Spongebob

"Duck Amuck", Daffy Duck cartoon where an unseen animator (a certain wabbit) constantly changes the scene and even Daffy's body

There was a sequel to this, where Bugs got the same treatmeny, and it ended up the artist was Elmer Fudd.

"Well, I finawwy got that scwewy wabbit! Heh-huh-huh-huh-huh!"

Theatrical:

1. Pink elephants scene from "Dumbo"

Not weird but very surreal.

It was a cartoon I saw a long time ago-I believe during an animation festival (well, it was basically 1 film that had a bunch of cartoon shorts in it). There was a baby in a room and the only thing that was in the room was a door. DON'T READ IF YOU DON'T WANT TO KNOW THE ENDING!!! The baby goes to try to open the door but can't. There is basically a flash of light and the baby is now a toddler. He still can't get the door open. Another flash a light and he is older. This goes on and he gets older and older. Finally he is an old man and finally dies-without ever opening the door. The door finally opens on its own and out pops an ironing board.  :o :o :o  I looked for it but couldn't find it-which is why I gave away the ending.  :D ;D ;D



Cat

Private Snafu "Rumors", especially that Theodore Giesal (aka Dr. Suess) worked on those cartoons