Writing about Kubrick films is difficult, because while he was obviously a great Director and produced movies with great scenes ( cf: HAL the computer, The boot camp with Lee Emerick, the attack on "The anthill" etc.) his movies are, on the whole, unsatisfying. The great scenes are usually accompanied with unengaging characters, simple-simon plots, and a lack of humanity. Such is the case with Clockwork Orange.
We have *individual* violent or nasty scenes of great power.
The gang rape and fight, the singing in the rain rape, the murder using a plastic penis, etc. The set design is creative and memorable even if it often verges on the pornographic. Yet, everything after Alec's arrest is dull as dishwater. As Ebert says the last 1/3 of the movie seems like the last 1/2. Equally dull are every interaction between Alec and his gang or his home life.
The Shocking Violence - not so shocking anymore
In 1971 many critics were shocked by the violence and found Kubrick's sympathetic portrait of a rapist-killer disturbing. Now, 50 years later, of course, we've all become so jaded with violence, sex and torture porn (cf: Game of Thrones) that Clockwork Orange seems almost restrained.
The Leading Character Book vs. The Movie
Kubrick seems to have loved taking famous books, written in first person narrative, and turning them into movies. Lolita, Barry Lyndon, and Clockwork Orange all have "Monsters" narrating their adventures (usually unreliably) and doing so in great literary style. None of this can be translated to the film. So, Kubrick ends up giving us unengaging lead characters. We can't sympathize or identify with them, they're objectively awful. And their actions when translated to film, have to be shown literally. We don't have an author filtering their actions through a lens of irony or humor. The result? On film - they're either disgusting or dull.
There's a big hole in middle of Clockwork Orange
We have a unsympathetic lead character that's in every scene, and he's impossible to care about. We end up observing him - like looking at a bug on glass. And that can be boring. Nor does the story about his "cure" hold any interest. So what's left? Just various scenes of violence, rape, and perversion. Which are well done from a technical standpoint.
Summary: This was my second viewing of Clockwork Orange and my opinion hasn't improved. Outside of some well done "sex and violence" there was nothing that kept me interested. All the greatness of the novel has been lost, and the last 1/3 is incredibly dull. One of Kubrick's biggest misfires. Rating **