7 of the Most Epic Fails in Literature

Before there was Failbook, Engrish, or Ugliest Tattoos, there was good ol’ fashioned literature: the fail that takes time to explain.

Here to demonstrate its rich and fail-tastic legacy are seven of the most epic fails in Western literature.

1. Herman Melville’s Moby-Dick

Captain Ahab’s Plan: To find and kill the famous white whale that took one of his legs.

The Problem: It’s a freaking whale.

The Outcome: Everyone but Ishmael dies.

Why This Fail is Epic: Having devoted his life to hunting Moby-Dick, Captain Ahab convinces his crew to join him in his quest. They spend over a year looking for the thing and when they finally find the whale, they battle it for three days – on the third of which it attacks (and destroys) their entire ship.

As his vessel goes down, Ahab makes one final attempt to harpoon the whale… only to wrap the rope around his neck and drown himself. Ishmael survives by floating away on a coffin.

The whale? Totally fine.

2. Shakespeare’s Hamlet

Hamlet’s Plan: To kill Uncle Claudius, who murdered Hamlet’s father, married Hamlet’s mother, and stole Hamlet’s (future) throne.

The Problem: Tapestries aren’t see-through.

The Outcome: Hamlet accidentally murders Polonius.

Why This Fail is Epic: At the beginning of the play, Hamlet swears to avenge his father’s murder. Following which he mopes, pretends to be crazy, ponders stuff, puts on an elaborate play about regicide to study Claudius’s reaction, and even blows a perfectly good chance to kill the guy because the timing isn’t right.

It goes on like this for two whole acts, until Hamlet finally does ONE proactive thing: he blindly stabs someone hiding behind a curtain. What could possibly go wrong?

Nothing, unless killing your girlfriend’s dad counts.

Here’s how the Danish dominoes fall: Hamlet, still pretending to be crazy, decides to act like the whole thing’s no biggie > His girlfriend commits suicide > Her brother challenges Hamlet to a duel > A lot of poison is involved > The queen AND both duelers all end up poisoned > Hamlet recognizes he’s at death’s door, goes, “meh,” and finally kills his uncle > The Norwegian army shows up to topple the government only to realize it’s totally overdressed.

3. F. Scott Fitzgerald’s The Great Gatsby

Gatsby’s Plan: To win back the woman of his dreams.

The Problem: She’s married. And really not worth it.

The Outcome: Gatsby and two other people die in a complicated murder/suicide love pentagon.

Why This Fail is Epic: You’ve just spent the past five years developing an elaborate alter-ego and amassing a fortune through the black market. You buy a mansion near the woman of your dreams and tell her you just “happened” to be in the neighborhood. You throw an endless party to ensure she makes her way to your house and then you rekindle the old flame.

Except that once you actually ask her to leave her husband, she backs off. You let her drive your fancy car home and she kills someone in a hit-and-run. You take the blame for her and the victim’s husband shoots you before turning the gun on himself. Your so-called sweetheart skips town with her abusive, adulterous husband and almost nobody shows at your funeral.

You probably spend your afterlife sitting around and waiting for her to return your angel-grams. (She probably doesn’t.)

4. Samuel Taylor Coleridge’s “The Rime of the Ancient Mariner

The Mariner’s Plan: You know that lucky albatross that’s been following our ship and seems to attract fine wind and good weather? How about I shoot it!

The Problem: He shoots it.

The Outcome: Immediately after the mariner shoots the albatross, the wind picks up and blows his ship into uncharted waters.

Then there’s a dead calm. For days. Everyone runs out of water. In the human version of forcing your dog’s face into its own droppings, the crew hangs the albatross around the mariner’s neck.

But wait, it gets better. Next, the crew 1) encounters a ghost ship that is 2) manned by Death incarnate, who 3) kills everyone on board except for the mariner, who is 4) left alone on a shipful of corpses until 5) the sea inexplicably turns into a slime pit filled with 6) slime beasties, which, because the mariner is so lonely, actually 7) become comforting to him – which is apparently the seafaring equivalent of saying “I do believe in fairies!” because after that, 8 ) the crew temporarily reanimates, sails to shore, and deposits the mariner on land to really think about what he’s done.

Why This Fail is Epic: See above.

5. Mary Shelley’s Frankenstein

Victor Frankenstein’s Plan: To recombine and reanimate necrotic human components into one big, cuddly B.F.F.

The Problem: Dead meat isn’t all that pretty to look at.

The Outcome: The instant Victor Frankenstein looks at his creation, he decides he wants nothing more to do with it and washes his hands of the whole experiment. (At least, we hope he washes his hands.) “I had selected his features as beautiful,” he insists, scratching his head. Who knew that a putrid patchwork quilt of human flesh could be so ickums!

Why This Fail is Epic: Contrary to what some of the movies would have you believe, Frankenstein’s monster (we’ll just call him “Frankie”) isn’t a mindless, grunting flesh golem with a criminal brain; he’s a lonely, articulate outcast who wants nothing more in the world than companionship.

It’s not until after Victor Frankenstein completely writes him off that Frankie begins those revenge killings.

Frankie even takes the time to explain his predicament to his creator, begging for a Mrs. Frankie to keep him company. But instead, Victor Frankenstein knowingly condemns him to a life of unbearable loneliness – probably while averting his eyes.

Let’s put it this way: if this were a romantic comedy, the entire dilemma would easily have been remedied with a stylist, some new duds, and a prom-date-bet-turned-life-lesson type of situation.

6. Edmond Rostand’s Cyrano de Bergerac

Cyrano’s Plan: To write beautiful and inspired love letters to the lovely Roxane on behalf of her inarticulate and not-all-that-bright wooer, Christian.

The Problem: Cyrano is also in love with Roxane, but because he isn’t good-looking, he doesn’t think she will ever reciprocate.

The Outcome: Cyrano’s mad writing skills successfully win Roxane’s heart. So thoroughly, in fact, that Roxane insists she would marry anyone who could write with such passion – even if he were – gasp! – ugly.

Just as Cyrano is about to admit that HE penned those letters, Christian is struck down in battle. Not wanting to get all awkward on his buddy’s deathbed, Cyrano decides to let Roxane and Christian continue believing what they want to believe.

Which is a nice sentiment in the moment, but guess what: fifteen years later, when Roxane is a lonely spinster mourning the “one that got away,” Cyrano is still secretly hoping that things will work out. Only as he’s about to die does he let it slip that Roxane should have been with him all along.

Why This Fail is Epic: You know those people who are so smart that they make a full circle right back around to being stupid? Cyrano is one of these guys. Here are a few things he doesn’t seem to get:

1) Cyrano sets Christian up to fail. Hard. If it weren’t for the fact that Christian is slaughtered before the marriage can go anywhere, he would undoubtedly have lived out the rest of his days as a MAJOR disappointment to his wife.

2) Cyrano’s letters trick Roxane into marrying under incredibly false pretenses. Some might call this the seventeenth-century equivalent of internet prowling. It’s not really something you do to be nice.

3) After fifteen years of allowing Roxane to believe that her soulmate is dead, Cyrano reveals the truth – juuuust as it becomes too late for her to do anything about it. Here’s to another decade and a half of regret, tootz!

7. J.R.R. Tolkien’s The Lord of the Rings: The Return of the King

Gollum’s Plan: To bite The Precious off of Frodo’s grubby little finger and then do a bumpin’ victory dance.

The Problem: Dancing on the edge of a fiery precipice is tricksy.

The Outcome: Clutching the One Ring (and Frodo’s finger), Gollum unceremoniously falls into – oh yeah – the one place in Middle-earth where this actually poses a problem.

Why This Fail is Epic: You’re five-hundred-and-eighty-some-odd years old. You have no family, no friends, no home, no clothes, and only one possession.

You like it a lot.

Ever since it was stolen about eighty years ago, you’ve been tracking it down relentlessly.

You’ve eluded men, elves, orcs, goblins, wizards, cave trolls, witch-kings, magic pterodactyls, and a huge freaking spider. You’ve finally gotten your mitts/chompers on the Precious when what happens? You misstep into a volcano.

The end.

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