Start of Darkness is the second of three print-only prequel books for The Order of the Stick.

While the first prequel book focused on the origins of the titular Order, this book focuses on the origins of Team Evil, and how Xykon, Redcloak, and the Monster in the Darkness came to become allies. Like the previous prequel, it delves into previously vague aspects of the story, such as how Xykon became a lich, how Lirian's Gate was destroyed before the events of the story, and how Xykon and Redcloak discovered the existence of the Snarl.

Note that the plot summary below is arranged in chronological order, to keep things coherent and easy to understand.

As a Recap page, all spoilers below are unmarked. You have been warned.

Start of Darkness provides examples of:

• Alcohol-Induced Idiocy: It turns out Eugene made his Blood Oath of Vengeance while heavily drunk.
• Aggressive Negotiations: According to The Dark One, his mortal life was ended in this manner. Considering that it led to his followers attempting to overrun human and elven lands and murder any humans and elves they could get their hands on, The Dark One rising as a vengeance obsessed god, and an even crueler repression of the goblinoids than what had come before, it doesn't seem to have worked out for anyone.
• Apologetic Attacker: Redcloak apologizes as he makes the decision to attack his brother, mortally wounding Right-Eye.
• Armor-Piercing Response: During the Sapphire Guard's raid on the goblins' village, Right-Eye left the safety of a cave and was nearly killed by a paladin. While Redcloak saved Right-Eye, another paladin killed their sister who was also in the cave. Years later, when Right-Eye decides to leave Team Evil, Redcloak asks him that if he ever thought that their sister would still be alive if Right-Eye hadn't left the cave. Right-Eye responds, "Honestly? No. I always thought that if I hadn't left that cave when I did, I would've been killed right alongside her. And I've got that same feeling now."
• Ask a Stupid Question...: When Redcloak meets the Monster in the Darkness for the first time:
  Redcloak: They call me "Redcloak".
  Monster in the Darkness: Really? Why?
  Redcloak: ...Because I wear black armor.
• Berserk Button:
  • Xykon has a slightly downplayed one about how wizards view sorcerers, starting after his encounter with Xavion.
  • The comic shows us why Redcloak showed a special dislike for Azure City and the paladins who live there in the main comic.
• Break Them by Talking: Xykon gives a truly nasty breaking speech to Redcloak which overlaps with "The Reason You Suck" Speech:
  Xykon: I now have every confidence that you will act to serve my interests from now on, even when I'm not really around to supervise you. I know that you'll protect my phylactery if my body is destroyed.
  Redcloak: You don't know that... I could wait until someone defeated you, and then—
  Xykon: And then face the realization that if you destroy my phylactery, you killed Right-Eye over nothing. Nothing at all. And you don't have the balls for that.
  Redcloak: I-I can raise him from the dead! I'm a Cleric, I just have to—
  Xykon: Ah, but he'll know. He'll remember that you killed him to protect me, and he'll know you for what you are: My willing slave. And man, you REALLY don't have the balls for that.
  Redcloak: What have I done?
  Xykon: So therefore, you're just going to continue following me and doing whatever I order you to do. Because as long as you're loyal to me, I'll let you pretend this never happened. We'll just go about our daily business, and you can hide from the horrifying truth of what you've become — namely, a murderer who just killed his own baby brother in cold blood. And hey, we can both pretend that you don't really have any options about any of the despicable actions I ask you to take from here on out — rather than acknowledging that, like Right-Eye, you do in fact have a choice. But unlike Right-Eye there, you're too chickenshit to ever make it. You'll obey me forever now, because I give you an excuse for your inexcusable behaviour. Now, are you going to stand there and tell me that I'm wrong?... Didn't think so. As a reward for your honesty there, I'll let you in on a little evil secret. What I said up there to Dorukan about overwhelming force? That's only part of Colonel Xykon's secret recipe for winning. It's not just about raw power, it's also about how far you're willing to debase yourself before feeling bad. And me? I ripped off my own living flesh so that I wouldn't have to admit weakness. You're strictly little league compared to that. That right there? That's the difference between bonafide true Evil with a capital "E" and your whiny "evil, but for a good cause," crap. One gets to be the butch, and one gets to be the bitch — Bitch.
• Brought Down to Normal: Lirian's virus is an ingenious method of doing this to any spellcaster who tries to take the Gate, which is ultimately only useful to spellcasters. Unfortunately for her, Redcloak was unaffected thanks to the Crimson Mantle and had the resources in his prison cell to turn Xykon into a lich, making Xykon immune as well.
• Bullying a Dragon: Eugene Greenhilt points out both that Right-Eye is doing this at one point, and the inherent foolishness of it. Right-Eye, disgruntled in his final days under Xykon's employ, covertly contacts Eugene and attempts to get Eugene to take out Xykon. Eugene refuses, and Right-Eye gets angry about it, and makes like he's going to attack Eugene. Eugene points out that if Right-Eye is trying to recruit him, then Right-Eye has clearly come to the conclusion that Eugene is considerably stronger and has a better chance at taking down Xykon, so attempting to threaten Eugene is a really bad idea, complete with a demonstration of Eugene's magical power. Right-Eye quickly backs down.
• Call-Forward: The Oracle calls Eugene "Ghost Dad". Eugene is confused, and the Oracle replies it'll be funny to those who read the webcomic. Funnier than the movie, at least.
• The Cameo:
  • Keith Baker, the Friendly Rival of OotS author Rich Burlew, has one in the book, as a candidate vying with Xykon and Yydranna to be chosen as the Number Two of The Unholy Master.
  • Look closely at the panel of Master Fyron giving a tour of his library. One visitor looks like Vaarsuvius, and given a elf's extended lifespan, just might be them.
• Captain Ersatz: Xavion is clearly one for Charles Xavier, aka Professor X, and his students are the X-Men.
• Celestial Bureaucracy: The epilogue sees Eugene Greenhilt being kept out of the Upper Plains by this, because he hadn't fulfilled his Blood Oath of Vengeance.
  Eugene: Oh, uh, no, I finished that. Must be clerical error.
  Deva: Our clerics don't make errors.
• Cerebus Retcon: There's a ton of it going on in this book. Just for starters we have the Character Development given to Redcloak, the fact that the goblins the Order killed left, right, and center in the Dungeon of Dorukan were ordinary goblin villagers literally forced to work for Xykon, etc.
• Chekhov's Gun: There are several that may or may not have still have a role to play in the comic. For example:
  • When Xykon first encounters the Monster in the Darkness, he puts an enchantment on it that will make it kill Redcloak and leave Xykon's phylactery, if Redcloak ever betrays Xykon.
  • Right-Eye's daughter is mentioned as having been smuggled to safety during The Siege of the Dungeon of Dorukan, and thus is presumably still alive and at large somewhere in the world.
• Co-Dragons: A young Xykon was this for awhile under The Unholy Master, but a Passed-Over Promotion made him angry enough to leave and attempt to become an Evil Overlord in his own right.
• Combat Pragmatist: Xykon can't overpower Fyron with magic, so he fakes defeat before beating the man to death with a trophy.
• Complaining About Shows You Don't Watch: invokedThe intro to the book is written in-character by Miko, who is disgusted at the reader for reading and buying the book, accusing it of being nakedly pro-Evil propaganda, while openly admitting she hasn't actually read it.
• Condescending Compassion: Xavion helps and teaches young sorcerers, but also freely admits to seeing them as inherently less than wizards.
• Covers Always Lie: The cover shows Xykon as a lich killing a paladin before his first encounter with Redcloak — while in the story proper, he wasn't yet undead when this happened. This is lampshaded on the last page of the book:
  MitD: Wait— the scene on the cover didn't actually happen that way.
  Demon-roach: Welcome to show business, kid.
• Darker and Edgier: The main comic certainly has dark moments, but there is no doubt that this prequel goes to much darker places than the main comic had at that time, and still is generally darker than the main comic. Genocide and the murder of one's own family are just the start of what happens during the course of the story.
• Deal with the Devil: Redcloak, at the end, describes his alliance with Xykon as such.
• Death by Irony: Throughout their lives, Right-Eye was the impulsive and rash brother while Redcloak was the careful planner. In his old age Right-Eye made a carefully-thought-out plan to kill Xykon, but was killed before he could thanks to Redcloak's impulsive decision to stop him.
• Defiant to the End: Redcloak's master mentions that both of the two previous bearers of the Crimson Mantle died at the hands of the Azurites and accepts that it's time for him to face the same fate. He then goes down fighting until his last breath, trying to save as many goblins as possible by getting the paladins to attack him instead.
• Didn't Think This Through:
  • When making Xykon a lich, Redcloak makes his holy item the phylactery, reasoning that this will give him control over Xykon by threatening to destroy it. When he makes that threat, Xykon points out that he only needs a Soul Jar for when his body is destroyed- meaning right then it's just a pricey ornament, one that can be replaced after Xykon finishes killing the two of them.
  • Also, Redcloak made his alliance with Xykon with the assumption that he could appease the elderly mage by giving him a life of comfort and pleasure in his final years after letting him believe that they would be taking over the world instead. Once Xykon is a lich, he no longer has any interest in those comforts or pleasures and he also doesn't have just a few final years left, he could potentially live forever. Redcloak never addresses exactly how he's going to deal with Xykon once the lich learns the true purpose of the Ritual and doesn't get the entire world handed to him on a silver platter.
  • Redcloak (almost certainly accurately), accuses Right-Eye of this at the Dungeon of Dorukan. Right-Eye's backup plan in case his attempted assassination of Xykon fails is to have his eye regenerated and hide among the other goblins, counting on Xykon not being able to tell them apart. Redcloak points out that Right-Eye is assuming that Xykon will give up when he can't find the particular goblin that attacked him, and Right-Eye doesn't seem to realize that Xykon's response will most likely be to massacre every goblin there to make sure that the one goblin who backstabbed him doesn't get away.
• Disaster Dominoes: In their second assault on Lirian's Gate, Redcloak uses the flame strike spell on a Treant. The burning Treant topples over onto a second, who does the same to a third, and so on until the entire forest is on fire, destroying the Gate.
  Redcloak: [as the Treants fall over] Hey, check it out: I got a two-fer! Ummm... make that a three-fer. Huh. Well this... This probably isn't good.
• Disowned Sibling: After spending the whole book calling each other "brother" out of disdain for their Line-of-Sight Names, Right-Eye's dying words are to call his brother "Redcloak" once the latter decides The Plan is more important than Right-Eye's life.
• Doomed by Canon: As a prequel novel, it was guaranteed that a number of things would have to end badly to set the stage of where the online comic began, or to fit various events that had been revealed in the main comic. This includes Xykon defeating Dorukan (and defeating or at least surviving a fight against any other foe he faced), Lirian dying and her Gate being destroyed, Redcloak failing to find a more peaceful way to live in the world, etc.
• Doomed Hometown: Redcloak's village is wiped out by Knight Templar Paladins from the Sapphire Guard early in the story, and his entire extended family except his younger brother are killed. Some of them, including his own mother, are killed right in front of his eyes.
• Downer Ending: Xykon succeeds in killing Lirian and Dorukan and takes over the dungeon. Redcloak decides to kill Right-Eye because he decides that he can't betray Xykon or else it would mean giving up on the Plan.
• Dragon-in-Chief: Thoroughly deconstructed. Xykon is essentially hired on to be Redcloak's dragon, but because Xykon is so much more powerful than Redcloak, Redcloak has no means of preventing Xykon from making foolish decisions or mistakes that kill off other goblins, and later loses any ability to control Xykon at all and can only watch as Xykon usurps the title of Big Bad.
• Dramatic Irony: Eugene Greenhilt tells Right-Eye to give up on killing Xykon. "When you're dead, you're never going to look back on your life and say, 'Darn, I didn't spend enough time on petty revenge.'" While that would normally be true (and very good advice), since Eugene died with his Blood Oath of Vengeance unfulfilled he was essentially Barred from the Afterlife, and he wishes he had spent more time on revenge. In the main comic, getting Xykon killed is now all Eugene cares about, if only so his Oath will be fulfilled and he can finally pass on.
• Draw Aggro: As the Azurite paladins begin slaughtering the goblin villagers, the previous bearer of the Crimson Mantle tells a young Redcloak to run, then loudly shouts at the paladins, calling attention to himself and declaring that they came for him, challenging them all to fight him. The paladins all leave the various goblins they're butchering and ignore Redcloak to go after the bearer. While he takes a number of them down with him, he's facing impossible odds and he knows it. The fight ends with the Bearer very, very dead.
• Dumbass No More: Alive, Xykon was powerful and ruthless, but also foolish and easy to manipulate. After being turned into a lich he becomes much smarter and starts seeing through some of Redcloak's plots and bluffs, and that was very bad news indeed for Redcloak and Right-Eye.
• Dying Declaration of Hate: Right-Eye does a rather more subtle one than usual. As he lays dying, Redcloak tells him "Goodbye, brother" and Right-Eye responds with "Goodbye... Redcloak." Right-Eye had refused to call Redcloak that title all throughout the story, instead insisting on calling him brother. He in fact, considers "Redcloak" to be something like a demeaning slave name put on for Xykon, so the fact that he calls his brother that with his dying breath is quite a rebuke and insult... and Redcloak doesn't even appear to notice it.
• Episode Zero: The Beginning: This book takes place even earlier than the other prequel book, and is labeled as #-1 on the spine because of it.
• Even Evil Has Loved Ones: Shown again and again. Tragically so, in many cases.
  • Redcloak starts his part in the story by watching in horror as his mother, uncle, older brother, mentor, and younger sister are killed in an unprovoked attack. He was shown to care for or respect them all.
  • Xykon has several, but they are definitely the exception to the rule for him. As a boy, Xykon genuinely loved his pet dog, and it was his grief over the dog dying that first let him access his magic powers and he accidentally brought it back to life as a zombie. Downplayed, however, since Xykon was the kind of creepy kid who immediately thought it was cool to watch the zombie dog eating other animals. Presumably he also cared about his grandmother, and that's why he secretly kept her around as a zombie after her death. Yydranna is the only other person that Xykon is shown to have a genuine bond with.
• Evil Cannot Comprehend Good: Xykon, who has cared for very, very few people in his long life, doesn't seem to get the fact that binding the souls of both Lirian and Dorukan in the gem gives the two lovers comfort and company for however long they're stuck in the stone.
• Eviler than Thou: Part of Xykon's speech to Redcloak was the longtime page quote. Most of Xykon's speech can still be found on the trope's quote page.
• Expy: Xavion and his school are a Parody of Professor X and the X-Men.
• Foregone Conclusion: It's a prequel, so of course the story ends with Xykon taking over Dorukan's Dungeon and Redcloak becoming completely subservient to the lich. It's even lampshaded in Eugene's trip to the Oracle of the Sunken Valley;
  Oracle: [in regards to Eugene's suggestion he come back for a second question] We're in the middle of a scene you don't remember in a narrated flashback framed by a flash-forward in a prequel book. There's no way in hell you're finding your way back here.
• Foreshadowing: When Xykon confronts Redcloak over the forest fire he started that destroyed Lirian's Gate, Redcloak insists that it's the fault of the druids for putting out tiny brush fires, contributing to so much dead growth waiting to burn. It's the first sign of his most damning flaw— the refusal to admit to his mistakes.
• Freudian Slip: While arguing with Right-Eye at the end of the book, Redcloak insists that every goblins' death were a necessary sacrifice for the Plan, and not his fault. This causes Right-Eye to realize that what's keeping Redcloak invested in the Plan is the Sunk Cost Fallacy.
• Gone Horribly Wrong: Turning Xykon into a lich backfires horrifically for Redcloak and his brother. It does get them out of Lirian's prison. It also makes what was originally Redcloak's strong-but-dumb patsie who would almost certainly die of old age within a few years of accomplishing their goals into something near-immortal, far more powerful and - most dangerously - smart enough to figure out what was going on. Very quickly, Xykon went from an Unwitting Pawn to the new Big Bad, all due to this one terrible decision. Right-Eye sees it. Redcloak can't admit that it was a mistake.
• Good Cannot Comprehend Evil: Right-Eye believes he can hide from Xykon's wrath by blending in with the rest of the goblin mooks who make up Xykon's forces. Redcloak points out that Right-Eye is assuming that Xykon's thought process will be "Well, I can't tell which goblin tried to attack me, I guess I have to let it go" the way a good person would. In reality, as Redcloak points out, Xykon is almost certain to respond by killing all the goblins there to make sure that his attacker doesn't get away.
• Great White Hunter: Lampshaded with the hunters who capture the Monster, who are members of the "Stereotyped Big Game Hunters Lodge".
• Gretzky Has the Ball: Played for Drama. As his wife Sara points out, Eugene Greenhilt could very easily learn the rules of any sport, but he clearly doesn't think that doing so would be worth his time, despite the fact that doing so would let him bond with his son Roy. It's a demonstration of how little he cares about Roy's interests that he adamantly refuses to do anything to bond with Roy over them or even just to talk about them in a minimally informed way.
• Gut Punch: We get introduced to Right-Eye's family, including his intelligent, snarky teenage son and gentle, loving wife. (And then are the two cute kids who have a great relationship with their dad.) We see them bond with Redcloak and the close ties within the family... and then all of them (aside from his daughter) are ignominiously killed off during a Time Skip by a group of adventurers that Xykon made no move to stop when they began killing his goblin followers. He was entertained by it, in fact.
• Heel–Face Turn: Right-Eye does one, and was close to making Redcloak do one as well, but then Xykon showed up and forcibly re-recruited all of them into Xykon's service.
• Hope Spot: Right-Eye had given up being a minion, and happily settled down and raised a family. He's on the edge of persuading his brother Redcloak to do so as well... and then Xykon shows up.
• I Don't Like the Sound of That Place: As a young man, Xykon spent time as an apprentice villain at the Helldeathdoomfire Volcano, home of The Unholy Master.
• Ignored Epiphany: Redcloak is ready to give up the Plan and try to do some good by building up the local goblin communities... then never thinks of it again after Xykon reappears and restarts The Plan.
• I Have No Son!: Right-Eye's dying words were to call his brother "Redcloak", a name he considered demeaning and symbolic of their servitude to Xykon, to cut ties with him after he chose Xykon and The Plan over him and the freedom of the goblin people.
• I Have Your Wife: How Xykon gets Dorukan to come out into the open. Reading in Serini's diary that Lirian and the human wizard were lovers, Xykon reveals to Dorukan that he has the elf druid's soul confined to a gem. Dorukan, who hadn't budged from his stronghold for months while Xykon and company besieged it (and who had spent years trying to unsuccessfully resurrect Lirian since her death), is out within ten seconds.
• I'm Dying, Please Take My MacGuffin: How the previous bearer of the Crimson Mantle passes it on to Redcloak, with the slight variant that he's already dead, and it's his spirit manifesting to urge Redcloak to take it.
• Immortal Immaturity: Right-Eye calls Redcloak out on how he hasn't changed in the climax, both figuratively and literally.
  Right-Eye: Life is about growing — growing older, growing wiser, growing closer to your loved ones. But you, you're frozen in time. You're the same angry kid who took that artifact off of your master's corpse that day.
• I Surrender, Suckers!: Xykon pretends to surrender to Fyron during their Wizard Duel, then beats Fyron to death with a trophy when the mage drops his guard.
• Kick the Dog:
  • Xykon has an endless stream of them in the book, between cruelty to animals, making an innocent plead for his life on the basis of I Have a Family and then killing the guy after Xykon had said he wouldn't, murdering people like Xavion or the waitress on a whim, forcibly recruiting Right-Eye's village into his army and then getting most of Right-Eye's family killed when he could have easily saved them, etc. Burlew wrote that one of the great challenges of writing the book was to make sure Xykon wasn't sympathetic once readers saw his whole story and experienced life through his eyes. "I mean, he's wholly and unapologetically evil, but more to the point, he's kind of a dick" is how Burlew sums up the matter.
  • The paladins wiping out the goblin village come across as doing this, since we see the goblins have no idea why the attack is happening and are simply trying to protect their loved ones.
  • Redcloak at the very least is doing this when he fatally wounds Right-Eye, and some readers considered it an outright Moral Event Horizon.
• Line-of-Sight Name: Redcloak and Right-Eye, in order to avoid being blasted by an impatient Xykon.
• The Loins Sleep Tonight: By the point where Xykon is transformed into a lich, he notes how that particular part of his body hadn't moved on its own in years.
• Mistreatment-Induced Betrayal: Right-Eye gets so unhappy with Xykon's callous disregard for the lives of the goblins working under him that, at two separate points in time, he tries to arrange for the sorcerer's death.
• Monochrome Past: The entire book is in black and white, with the exception of Redcloak's exposition on The Dark One and the Snarl.
• Motivation on a Stick: Before Xykon decided to use Lirian's soul, the goblins tried to lure out Dorukan with a book on a fishing hook. Needless to say, it didn't work.
• Must Have Caffeine: Xykon has a brief Villainous Breakdown upon discovering that his physical senses have perished along with his mortal flesh, and he can no longer taste or enjoy coffee. He replies by flying into a Tranquil Fury and offing minions around him until his rage is sated.
• My God, What Have I Done?: Redcloak's reaction to killing his brother, once Xykon reveals it was for nothing.
• Nice Job Breaking It, Hero!:
  • Nobody on Team Evil, not Redcloak, Xykon, or even The Dark One, knew there was more than one Gate until Lirian, knowing her Gate had been destroyed, told Xykon that her he'd never be able to get control of one of the other Gates.
  Lirian: Even if you locate them, my friends will stop you from conquering the other four Gates.
  [beat panel]
  [beat panel]
  Xykon: Did you— Did you just say, "the other four Gates"?
  [beat panel]
  Lirian: Crap. [Xykon snaps her neck]
• No Name Given: The real names of Xykon, Redcloak, and Right-Eye are never revealed. Xykon is a made-up "cool name" that his teenage self came up with, while Redcloak and Right-Eye are Line-of-Sight Names, and they spend the entire comic calling each other brother... until Right-Eye's final words.
• Once More, with Clarity: In the webcomic proper, we only get a single panel of Xykon killing Eugene Greenhilt's mentor, which looks like he's using a spell to do the job. In this book, we see what really happened; Xykon had already killed Fyron through blunt force trauma by that point, and was turning his corpse into a zombie.
• Overly Long Name: When the leader of the lizardfolk petitions for Xykon's help, he introduces himself as "Ekdysdioksosiirwo, Viridian Lord of—". That's as far as he gets before he's Killed Mid-Sentence by Xykon with lightning, who remarks, "Yeah, that's too long to remember." For this reason, the Bearer of the Crimson Mantle introduces himself and his brother as "Redcloak" and "Right-Eye" respectively.
• Passed-Over Promotion: Xykon was actually OK with getting passed over in favor of the evil mage Yydranna, as he admits she's good at what she does and he genuinely respects her. Being passed over in favor of Yydranna and Keith Baker, however, pissed him off to no end and he angrily decided that it was time to end his service to the Unholy Master and go Start My Own.
• Pass the Popcorn: Deconstructed. Sometime between Right-Eye's village being enslaved and the siege on Dorukan's Dungeon, adventurers attacked Team Evil's forces, resulting in the deaths of Right-Eye's family. As Right-Eye hatefully notes later on, Xykon could have intervened, but found the carnage amusing and let it go on so he could enjoy the show.
  Right-Eye: For fun. He watched my family die FOR FUN!!
• Pragmatic Villainy: As a mortal, Xykon declines to have anything to do with a scheme that involves kidnapping virgins. Not because he has moral qualms about it, but because if he's going to turn a woman into a Sex Slave, he'd prefer that they have some experience and know what they're doing.
• "The Reason You Suck" Speech: Just before going to attempt to kill Xykon, Right-Eye calls out Redcloak for a number of his faults, his true motive for refusing to turn on Xykon, and wasting his life by serving both an insane lich and a god that Right-Eye has come to view as petty, callous, and cruel.
• Regretful Traitor: Redcloak deeply regrets betraying and killing his brother, and continues to be haunted by the deed long afterward (as shown by the 5th and 6th panels here), but rationalizes that he had to do it for the sake of his entire race. (In truth, Right-Eye is correct and Redcloak simply can't face the responsibility of admitting that he is responsible for the deaths of all the goblins who died due to Redcloak's refusal to Know When to Fold 'Em with regards to his bad deal with Xykon.)
• Secret Test of Character: Xykon knew Right-Eye had a dagger that could harm him, but he simply used it to see where Redcloak's loyalties lay. Redcloak passed the test (or failed it, depending on your point of view.)
• Self-Made Orphan: Teen Xykon kills his own parents.
• Sense Loss Sadness: Xykon really doesn't care about losing the majority of his flesh. But losing his tongue - and more importantly, losing the ability to taste coffee - really hurts.
• Significant Name Shift: Redcloak and Right-Eye use those nicknames for Xykon's convenience but otherwise always call each other "Brother" in private. When Redcloak murders Right-Eye to protect Xykon and the Plan, Right-Eye calls him "Redcloak" with his last breath.
• Smash Cut: When Xykon decides to be an independent villain;
  Xykon: How can I best bring the world to its knees? Ah! I have it! I'll just—
  [cut to Xykon in a jail cell as a pair of paladins look on]
  Paladin: Looks like we caught you dead to rights, necromancer!
• The Starscream: The Unholy Master openly acknowledges that whoever he chooses for second-in-command will almost certainly fall under this trope. True to form, Yydranna is ready to start plotting his assassination once lunch is done, just so she can give Xykon some advice.
• Start My Own: After the Unholy Master refuses to promote him, Xykon decides to leave his service and become an evil leader in his own right.
• Start of Darkness: For Redcloak, anyway, as we see the traumas that made him a Well-Intentioned Extremist and the rationale behind his actions. Xykon, as we see, was pretty horrible from early childhood.
• Sunk Cost Fallacy:
  • Redcloak just barely manages to convince Xykon to keep going with The Plan using this as part of his argument to get Xykon to keep going. It's very clear that Xykon was basically flipping a coin in his mind about whether to kill Redcloak anyway.
    Redcloak: If- if you kill me, then you'll never rule the world. Only I know the secret rituals to control the Snarl. [beat panel] You will have gone through this change for nothing. [beat panel]
    Xykon: [throws both Redcloak and Right-Eye through a window] Fine. But from now on, I'm in charge here. You each obey every order I give you or I simply snuff both of you out.
  • The main reason why Redcloak ends up Trapped in Villainy with Xykon. To stop would mean everything he did, up to and including killing his brother, was for nothing. This is even lamphaded by both Right-Eye when he calls his brother out and by Xykon in his Eviler than Thou speech.
• Together in Death: Xykon unwittingly causes this by binding the souls of Lirian and Dorukan to the same Soul Gem. Due to Evil Cannot Comprehend Good, he thinks he's inflicting And I Must Scream on them, but it works to reunite the two lovers and give them comfort they otherwise wouldn't have.
  Lirian: Dory? Dory, is that you?
  Dorukan: Yes, my love. I've failed. It looks as if I am to share your prison forever now ...
  Lirian: No, no... not a prison anymore. [they embrace]
• Took a Level in Badass: As the book covers more than 100 years, we see this happen repeatedly to both Xykon and Redcloak, but more noticeably with Xykon. With time Xykon goes from a kid who doesn't know what he's doing with his powers, to a small-time villain helpless to do anything more than stand there and take it as the authorities who've arrested him crack cheesy jokes at his expense, to a major threat, and finally, to one of the most dangerous beings in the world who has singlehandedly killed off at least two different epic level spell casters, not to mention Fyron, who had to be high-level at least (as Eugene Greenhilt's mentor).
• Tragic Monster: The main focus of the story is seeing how Redcloak became one.
• Tranquil Fury: When Xykon finds out that being a lich means not being able to taste coffee^note since his tongue dissolved with the rest of his body, save the skeleton, he doesn't raise his voice. He doesn't throw a tantrum. He just starts killing whoever gets within arms reach, and after Redcloak narrowly avoids death with a Sunk Cost Fallacy, he very coldly names himself leader of Team Evil without another word.
• Trapped in Villainy: Right-Eye and the rest of the goblins of his village are once Xykon forcibly recruits them. Played with in Redcloak's case, as halfway through the novel and again at the end, he essentially chooses his own fate.
• Villainous Breakdown: Xykon has a brief one of these upon discovering the loss of his earthly senses, in particular the implications for his former enjoyment of coffee. He deals with it by murdering minions around him and coming within a hairsbreadth of doing the same to Redcloak.
• Villainous Friendship:
  • A number of examples, but the story goes to great lengths to show that Xykon and Redcloak are not friends at all. Readers who read the webcomic back when it looked like Xykon and Redcloak might have a case of this got a nasty shock at the end of the book.
  • Yydranna the wizard is probably the only person the Xykon ever genuinely liked.
• Villain Has a Point:
  • The reason the Unholy Master passes Xykon over for promotion is because the sorcerer has the strategy of a rabid wombat, who just blasts his enemies with magic without bothering to think any further than that. Yddranna agrees with this analysis, and warns Xykon to to put more thought into his plots if he wants to make it as an arch-villain.
  • This is what makes Xykon's Breaking Speech so painful for Redcloak; the lich is 100% right.
• Wham Line:
  • Xykon revealing he was fully aware that Right-Eye was plotting behind his back.
    Xykon: Huh. First you blast your brother, then you lie to me about it, now this? Did they have a big sale down at the Testicle Store or something?
  • And then right after that...
    Redcloak: Wait— you knew in advance?? Why didn't you stop him before it got this far?? Kill him or something?
    Xykon: Why, I would have thought that was obvious. I wanted to see if you would kill him for me.
• What Happened to the Mouse?:
  • Where is Right-Eye's daughter?
  • Was the Soul Gem with the souls of Dorukan and Lirian destroyed when the Dungeon of Dorukan was obliterated at the end of the webcomic's first arc? Or is the gem still intact somewhere?
  • What happened at the Helldeathdoomfire Volcano with the Unholy Master and Yydranna after Xykon left?
  • When Xykon first embraced villainy, did he stop with simply killing his parents and leaving, or did he wipe out the whole village? If nothing else the scream of his parents might have drawn attention and resulted in neighbors approaching, and one can easily imagine even a teenage Xykon killing those people with his magic or letting his zombies attack them.
• Wizard Duel: Several are seen:
  • The first is between Xykon and Eugene's master Fyron. Fyron beats Xykon with magic after a prolonged duel, but is then beaten to death by Xykon.
  • A mortal Xykon and Lirian start to have such a duel, but it has barely begun when Lirian's virus erases Xykon's spellcasting abilities. Xykon pays Lirian back later when, now a lich, he catches her by surprise and curbstomps the Elven druid.
  • Later, we see Xykon take on Dorukan, and Xykon wins because of Boring, but Practical tactics and the advantages granted by being undead. (And black and white artwork negating Dorukan's attempt to use the prismatic spray spell.)
• You Are Worth Hell: Dorukan and Lirian aren't too unhappy to be trapped in a Soul Gem forever, since it means they get to be Together in Death.
• Your Soul Is Mine!: After killing Lirian, Xykon uses Soul Bind to trap her soul in a black gem, specifically to spite her beliefs in the cycle of life. He later does the same thing to Dorukan, ironically helping the two lovers be Together in Death.