A Clockwork Orange.

Anthony Burgess’ A Clockwork Orange appears on the three major lists of the best books of the 20th century (Modern Library, Radcliffe, and the TIME 100), one of 25 books to pull off the trifecta. It’s a masterwork, a deeply philosophical novel that poses serious questions about liberty and free will, as well as a linguistic tour de force written in a brilliantly expressive invented slang.

The novel is narrated by Alex, who refers to himself as “Your Humble Narrator,” a teenage tough called a “droog” who spends his evenings causing mayhem, assaulting older citizens, dabbling in the occasional rape, and listening to dramatic pieces of classical music. Eventually arrested in a home invasion gone awry, Alex spends two years in prison before he’s offered a chance to gain his freedom in two weeks if he submits to an experimental treatment known as the “Ludovico Technique,” probably the best-known sequence from the book or the movie version, where Alex is forced to watch violent films with his eyelids held open. In its final third, Alex re-enters society and the questions begin: Is a man still a man if he’s acting morally by force rather than choice? How much do we want or expect our government to do in the name of public safety?

Burgess created his own slang for the novel to give it a futuristic or alternate-history feel. Most of the new words draw from Russian vocabulary – “nadsat,” meaning teenager, from the endings of the Russian words for the numbers between eleven and nineteen; “viddy,” to see, from the Russian “vidyet” – with occasional invented slang words, like “sinny” for the cinema. It makes the first few pages of the book a bit tough to get through, but after a while, it becomes easier to follow and adds color to Alex’s language, sometimes sarcastic, sometimes almost musical, while also creating a clear delineation between his speech and that of the adults around him.

My senior year in high school, I took an AP lit class with Mrs. Glynn – who saw phallic and “concave” symbols on every page of every book – and she assigned us a choice of one of three books: Slaughterhouse-Five (also on all three top-100 lists), Catch-22 (ditto), and One Flew Over the Cuckoo’s Nest (omitted by Modern Library). I ended up reading and enjoying all three, since they presented moral or philosophical questions, often about horrible situations, with heavy doses of humor and a thoroughly modern tone. A Clockwork Orange would have fit perfectly on this list, and if anything, Burgess’ novel is more clever and more serious than the other three.