My Villainous Fantasies, Part 3, the Finale: The Coolest Villains of All Time

These aren't characters I have fantasized about being.  They're just really cool villains.

Laplace's demon or just a cryptic cat that likes to screw with people's heads?  Either way, the Cheshire Cat is very cool, but tragically did not make the cut!

We all have our favorite villains.  Maybe they're the villains we fight in our fantasies.  Maybe they're villains we identify with.*  Maybe they're just great concepts.

This list was the hardest to come up with because there just are so many cool villains out there!

* This footnote has nothing to do with villains.  I'm just pointing out that I know I ended a sentence with a preposition, which is a grammatical taboo.  However, the alternative is to use "whom," which comes off as pedantic.  If anyone has found a solution to this, please let me know.


Honorable Mentions
(As always, beware!  Spoilers are lurking about!...)

Too many to name.  Here's a brief listing of a handful of the top contenders.

Ahab [Moby Dick, 1851 book] is one of the coolest characters ever written.  Whether or not he's a villain or just a compulsive could be the subject of endless debate.  However, his obsession with revenge against the mindless whale and his willingness to sacrifice not only himself but his crew on the alter of personal vengeance makes him evil enough to qualify as a villain, imho.  What makes him cool are quotes such as this:

"Speak not to me of blasphemy, man; I'd strike the sun if it insulted me. Look ye, Starbuck, all visible objects are but as pasteboard masks. Some inscrutable yet reasoning thing puts forth the molding of their features. The white whale tasks me; he heaps me. Yet he is but a mask. 'Tis the thing behind the mask I chiefly hate; the malignant thing that has plagued mankind since time began; the thing that maws and mutilates our race, not killing us outright but letting us live on, with half a heart and half a lung." - Ahab

Ahab: completely freakin' nuts, but cool as heck.

Alex, from A Clockwork Orange [novella, not the movie] was a close one, too.  In fact, he was so close he was in the top three until I started typing.

Alex is awesome because he is the face of the irredeemable, unrepentant psychopath and hedonist.  His villainy is for nothing but pleasure.  Burgess's novel is particularly brilliant because I really feel that Alex is the expression of his own antisocial tendencies as a writer and philosopher.  Unlike the movie, which I feel is mere shock, the book is incredibly thought provoking.

The Cheshire Cat from Alice's Adventures in Wonderland [1865 book] is also a wonderful villain.  While he doesn't do anything villainous, his taunting answers to direct questions which simultaneously give the image of both sense and nonsense make him incredibly irritating to all the other characters in the book.  I love him because I think he's one of the few characters who is not irritating to the reader but is so frustrating to the other characters he's actually evil.

Tribbles, the furry little exponentially multiplying organisms from the original Star Trek series get an honorable mention simply because they're such a cool concept.

Can mindless evil also be adorable and fuzzy?  According to Star Trek, yes, yes it can.

Two incredibly serious villains that I adore are from the same Shakespeare play, Titus Adronicus: Titus, the protagonist, and Aaron the Moor.

Titus, like Ahab, is so bent on pleasing the Emperor of Rome that he utterly destroys himself and his family.  This ultimately leads to a complete mental collapse where he turns on Rome, the Empire, and the evil Queen of the Goths.  Thus, Titus spends most of the play as a tragic antihero and ends the play a psychopath.

Aaron on the other hand is cool for many of the same reasons that Alex is cool: he is totally irredeemable and unrepentant, as his speech from the gallows demonstrates.  Yet, unlike Alex, who appears to engage in villainy for the same reasons as Caligula, Aaron also has some of the same features as Frankenstein's monster: the world has condemned him and abandoned him and thus he has condemned and abandoned the world.  A great story, a great character.

Anthony Hopkins ably played the lead role of Titus in the 1999  movie Titus.  The movie's language isn't updated; it is actually a very imaginative, well-directed version of the play.  Probably also doesn't hurt that I am one of those people who would watch Anthony Hopkins eat a plate of nachos for 30 minutes.  

An entire separate series of posts could be done on the villains in John Carpenter movies.  While one of his most famous, Mike Meyers from the Halloween slasher series is probably the first that comes to people's minds, the coolness of the villain in Halloween pales compared to the unstoppable chimeric evil in The Thing or the kitschy evil that provides the vehicle of social commentary in They Live.  His classic antiheros, such as Snake from Escape from New York, have even inspired other media.  John Carpenter: master of cool villainy.

The Winners

Frankenstein's Monster, Frankenstein; or, The Modern Prometheus [1818 book]

Frankenstein's monster in the novel is an amazing character.  Dr. Frankenstein set out to create a creature of unsurpassed intellect and beauty.  He was successful in the first - the monster is a genius - but in the second Frankenstein failed.

Abandoned and held contemptible to society through no fault of his own, the Monster, though initially loving and forgiving, turns against humanity and seeks revenge through murder.

A great story of how even a gentle heart can turn because of society's narrow minded cruelty.

The Id of Dr. Morbius, Forbidden Planet [1956 movie]

I am extremely hesitant to put too much information on this villain simply because it would ruin one of my favorite movies of all time, Forbidden Planet.

Forbidden Planet is one of the greatest science fiction stories from any time period and played a huge role in the development of science fiction during the Golden Age.  A classic adventure mixed with almost prescient social commentary, it is a must watch for any true science fiction fan.

HAL, 2001: A Space Odyssey / 2010 [multiple books and films]

Mad?  Evil?  Or tragic hero of the rational?

HAL, the superintelligent computer from the 2001 / 2010 book and movie series wins for coolest villain of all time.

It's not that he's the most powerful or most dangerous.  But he's the best mechanism to explore motivation and questions of free will that I've ever approached.

HAL's problem is that he values the objectives of the mission more highly than the safety of the crew. In a certain sense, he's very much like Ahab: he has a goal that is more important than the people around him.

Yet, unlike Ahab, most of us would agree that HAL's goal is noble and logical.  For both science and for the larger safety of mankind, HAL is obligated to disregard the safety of the the crew aboard Discovery One.

From the perspective of Bowman and the rest of the crew - and the audience, who knows the crew personally and identifies with them - HAL is evil and insane.  Yet, to a more distant observer, perhaps HAL made the right decision.  Perhaps the individuals aboard the ship matter little compared to the safety and knowledge of all of mankind.

HAL is the the source of an infinite array of potential philosophical questions and musings.  Therefore, he is, at least to me, the coolest villain of all time.