How many times has 'The Simpsons' referenced 'A Clockwork Orange'? I can think of four.

Cafe Society
1

In no particular order:

  1. In the last Treehouse Of Horror, a direct spoof of ACO with Moe as the Malcolm McDowell character
  2. In a much earlier T Of H, Bart was wearing a costume of the Malcolm McDowell character, but it wasn’t a plot point of any type that I can recall
  3. The episode where the dog (Santa’s Little Helper) runs away, he’s brainwashed ACO style into become one of Burn’s hounds
  4. This one was subtle, and I didn’t catch it until reading about later. There was an episode where Lisa brainwashes Bart against cupcakes, and the scene where he tries to grab some but freaks out is a spoof of a similar ACO scene where the Malcolm McDowell character tried to grab boobs but has the same reaction.

Any others ?

2

In “Homer the Smithers,” Burns falls out a window and ends up in bed wearing casts, with Smithers feeding him.

“It’s a remarkable thing - in the short time you were gone, I learned to be completely self-reli- [gulp] -ant.”

3

Can’t cite the episode, but I remember Bart complaining–in a British accent–of a “bit of a pain in the old Gulliver.”

4

Bart the General
``There’s been a horrible ghastly mistake.’’

Duffless
the cupcake scene

Homer goes to College
Homer’s eyes are being held open to study

5

Nine times