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Not that the comic is exactly "light and fluffy", but prequel book Start of Darkness is significantly darker than the online comic's average tone.
Things have gotten a turn for the dark starting around comic #823. The Resistance falls arc and three teams are headed for the same gate: Team Evil, the Order of the Stick and The Linear Guild. And then the entire Draketooth family turns out to be dead, and guess who's responsible?
Dark Is Not Evil: Invoked by Belkar after Haley assumes that V's new black robes, glowing eyes, and evil whispers mean that s/he's turned evil. Belkar, too, is convinced of that, but defends Vaarsuvius with this argument just to mess with everyone's heads.
Deadpan Snarker: Most of the characters fall into this at some point, but Roy took extra points in this skill. Vaarsuvius comes only second to Roy in the snark, and being The Spock he's even more deadpan. And V's raven familiar seems to take after his wizard. On the villain's side, Redcloak is no slouch either.
Death Is Cheap: Not literally; coming Back From the Dead is actually rather expensive. But price aside, it's usually not all that difficult, except when the plot requires it to be, as in Roy Greenhilt's case, or in special situations like being killed by the Snarl or dying of old age. This is Lampshaded to the extent that a character calling for reinforcements (Haley in Old Blind Pete's cellar) suggests they bring the wherewithal to resurrect her and her friends. Also, you can apparently do the old "challenge Death to a game for your life" thing. And you can pick Wet T-Shirt Contest as your game.
The prequel books are fully in greyscale. According to the author, this is to give them a "nostalgic" feeling, since these are the "home movie" of the OotS characters. Which is mostly a joking explanation — the primary reason being costs.
During the siege of Azure City, Roy beheads Xykon's undead dragon. The head crushes a Death Knight that is overwhelming Vaarsuvius; V later complains that it was a lame "deus ex machina".
When V cast Familicide on an ancient black dragon in "If They Pull a Knife... ", the first victim is a black dragon currently battling against a pair of adventurers — who are left wondering just what the heck caused their opponent to inexplicably drop dead in front of them.
Dirty Coward: Thanh accuses Redcloak of being one when he decides to attack the resistance directly, but for the most part uses summons to fight against them. In truth, he simply prefers not being a front-line fighter. And he does actually fight a few of the paladins directly...with gruesome results.
This is the main motto of Nale and the Linear Guild, even mentioned on their business cards.
Vaarsuvius. Ancient Black Dragon. "Familicide!"
Tiamat is promised five good dragons dead for every black dragon killed by V.
General Tarquin offers to give the pair of bounty hunters 8,000 gp for their trouble in accidentally bringing in Elan instead of Nale. Gannji then demands 50,000 instead because he has a thermal detonator (which is actually a soup can — he was just keeping up a Running Gag). Tarquin then "misplaces" some court paperwork, leaving the bounty hunters sentenced to die in the arena for attempting to extort him in front of his son.
Elan, when he's not The Fool, or both simultaneously.
Celia has her moments, explained in part by her status as an Outsider and therefore someone not familiar with the customs of the Material Plane. She's also from the Elemental Plane of Air, making her an "airhead".
Subverted in "Neutralize Elf" — Haley pushes Elan out of the way of a poisoned bolt, only to have it hit V.
Do Not Do This Cool Thing: Yeah, yeah, we know V's genocide of the black dragons was evil. But damn was it powerful, damn did it look awesome, and damn it if comic #639 didn't vicariously satisfy every major revenge fantasy the readers have ever had. In fact, the entire Soul Splice arc did wonders for V's character depth and popularity, regardless of any evil things V did in the storyline. Antihero-esque lust for power combined with insufferablesnarking and heroic desperation? PSL Webcomics page, here we come!
As Roy points outhere, the Order is usually at some disadvantage when they fight their Evil Counterparts. Despite Roy's caution, it happens again when Vaarsuvius gets himself incapacitated by a trap right before the Linear Guild attacks.
Ultra-powerful soul-spliced Vaarsuvius is literally the most powerful mage to have ever existed...as long as he/she holds on to the splices. Good thing one of them slips away BEFORE the elf goes to fight the Big Bad, Xykon, or else the series would have ended in a curb stomp.
An Angel "of pure Good and Law" clears the heroes' names, making them innocent of a very serious crime in the eyes of an order of paladins. However, the trial is just a Sham Ceremony, and the "angel" is just a manipulative ghost disguised as an angel.
The evil trio who tempts V takes on the role of Enigmatic Empowering Entities, but subverts the role to snare the wizard. V is manipulated into accepting a price s/he doesn't understand and is tricked to believe that s/he has an excuse to let her more destructive tendencies run wild without accepting true responsibility for the havoc. Also, the power they give is tainted and fatally flawed in itself, not at all what V had imagined "Ultimate Arcane Power" to be.
Equal Opportunity Evil: The Lawful Evil Empire of Blood employs humans, lizardfolks and kobolds indiscriminately, from the lowliest foot soldiers or slave drivers to the upper echelons of society, including the Empress' main counselors (with a human general, a lizardfolk high priest and a winged-kobold chancellor).
Escalating Brawl: The argument between Roy, Gannji and Enor ends up in a serious pub brawl.
Vaarsuvius was already aware of this, chose to ignore it, and is likely to pay some consequences in the next plot arc.
As revealed in the Start of Darkness prequel, Redcloak's plan, hatched by the god of goblinoids, the Dark One, to have a powerful divine and a powerful arcane caster manipulate the Gates to control the Snarl without completely releasing it, and then use the Snarl to force the other divine pantheons to give equal rights to the goblinoids and other humanoid "monsters" solely created to be experience point sword fodder for clerics of the other, older races. Redcloak is well aware that this might end with the death and unmaking of himself and Xykon, but is still determined to go through with the Plan.
Similarly, in Start of Darkness, Redcloak learns the hard way that Xykon is not a toy, or even a tool. Subverted, as it turns out; Redcloak still thinks of Xykon as a tool, just one which takes a little more skill than most to use. Whether or not this assumption will come back to bite him in the arse again, time alone will tell.
Evil Is One Big Happy Family: Even though it's the Trope Namer, subverted constantly. Evil characters don't care about the alignment of other characters, only whether or not they will help or hinder them in achieving their goals.
Lee: Don't be silly, why would we want the lich to win?
Note that the IFCC, despite defying the trope in the above quote, also play it completely straight, since their long-term goal is to forge a truce which will unite the warring fiends in an alliance against the forces of Good.
The Giant seems to enjoy playing with the Faux Affably Evil trope in general: Redcloak averts it, both before and after his My God, What Have I Done? (before it, he doesn't bother to show the slightest concern for the hobgoblins, and after he genuinely does care about them), and Miko inverts it via Good Is Not Nice, though she's not so good after she kills Shojo, hence her being removed from paladinhood.
Evil Power Vacuum: Averted; Celia convinces Haley not to kill Bozzok, leader of Greysky's thieves guild, in order to stop a power vacuum being created.
Nale, Elan's twin brother, who multiclassed as fighter/rogue/sorcerer specializing in enchantments (instead of being a bard like Elan);
Samantha, the spoiled sorceress daughter of the leader of the bandits of Wooden Forest;
Tsukiko, the evil mystic theurge (technically she is both a divine and arcane caster); Jirix brings that up when he questions whether she planned to betray the group, since she could potentially take control of the Snarl single-handedly provided she knew what to do.
Qarr the Imp;
Jephton the Unholy, the sorcerer-archmage used for Vaarsuvius's soul splice.
Xykon conducts a job interview while storming the Azure City castle.
In the hypothetical scenario the archfiends suggest to Vaarsuvius instead of accepting their offer, V's master Aarindarius is shown defeating a powerful dragon while reading a book, not even bothering to look in its direction.
Exotic Entree: The banquet that Elan's father Tarquin holds in his honor. Poor Elan, not being the sort to enjoy such dishes, loses his appetite rather quickly.
Face Doodling: Elan and Belkar do it to Roy when he's paralyzed by a poison trap.
Face Heel Turn: Averted in "The Power of Immediate Gratification", where Belkar, of all people, gives up the chance to join a cause that'll let him do all the killing he wants. Admittedly, Belkar leaves something to be desired as a "face", but the other side is even worse, so....
Fake High: In "Madness", a being from the Lower Planes explains why Vaarsuvius (under the effects of a "soul splice") appears to have shifted more towards Evil on the character-alignment scale by presenting a college-university analogy: "It's like if you were at a party where someone has been drinking beer that they didn't know was non-alcoholic: They might seem drunk anyway, just because they were expecting it."
False-Flag Operation: Tarquin places his allies as advisors and uses them to manipulate rulers into conquering the western continent.
Basically Redcloak's motivation both ways. His family was slaughtered because paladins don't consider his kind to have the right to exist, so he blames all humans for the actions of that group and kills them freely.
Classism: Wizards in general and Vaarsuvius in particular seem to look down on the other magic-using classes. Sorcerers are usually the targets, but being called a warlock is a dire insult.
Far East: (Or Far South, as the case may be.) Azure City would be a Fantasy Counterpart Culture for Japan, if it were at all consistent. Instead, names like "Miko Miyazaki" stand side by side with names like "O-Chul", and the people worship the Twelve Gods, the animals from the Chinese zodiac. This, naturally, is a pastiche of D&D's Oriental mishmash settings, most specifically the Oriental AdventuresSourcebook.
On the Origin of PCs has Roy claiming that belief in the complete supremacy of arcane magic is a common flaw among spellcasters.
Thinking he knows more about a situation than he actually does is Roy's Fatal Flaw. If Roy had known that liches can regenerate from a phylactery from the very beginning, he could have made sure Xykon was Deader Than Dead and wouldn't have been able to return to kill him later. This also lead to Miko becoming wrongfully suspicious of Roy, with disastrous consequences. In a Too Clever by Half moment, he also believed he had outsmarted the Oracle when the latter was more than happy to just tell him which Gate Xykon was headed towards next. Later, he dismissed the Celestial's warnings about V's Deal with the Devil because he thought she was talking about Belkar.
The Ancient Black Dragon intended to bind Vaarsuvius' children souls to it forever, and Xykon has a fondness for trapping the souls of important enemies in gems. This is subverted when he imprisons Dorukan in the same gem as Lirian.
A slightly more humorous example: after willingly being abused and used as a weapon by Belkar in order to not be destroyed, the head of the "Eye of Fear and Flame" (one of Xykon's three decoys) finally draws the line when the latter announces his intentions to eventually use him as an "emergency chamber pot".
Final Solution: Vaarsuvius's partner and children are threatened by a vengeful dragon. Fueled by demonic and devilish magic, Vaarsuvius finds a solution to the problem: Vaarsuvius kills not only this dragon, but also any dragon that is in any way related to it — a quarter of the Black Dragon population — to stop any threat to his family.
Fire-Forged Friends: Blackwing resents being Vaarsuvius's familiar, due to V's neglectful behaviour towards him for most of the comic. But when they're forced to work together in an attempt to destroy Xykon, they put aside their differences and learn mutual respect for one another.
After defeating a Black Dragon, the party realizes he was just an underling of the real guardian of the cave. The real guardian of the cave? His mom. Uh oh. Plus, the Black Dragon in the cave mentions his mother while talking to V. For extra fun, read V's dialogue in strip #338. Spoilers, ahoy!
Plus #572, specifically when the Oracle tells Roy why he wants him gone.
Also an extremely subtle one in #600. See what Eric is playing with?
Girard Draketooth isn't just your basic fantasy Awesome McCoolname. He's the grandson of a dragon. A dragon related to the one Vaarsuvius nailed with Familicide. Oops.
Forging Scene: Appears with the reforging of Roy's greatsword intercut with shots of other characters preparing for the upcoming story arc. Also notable in that it's one of the few forging scenes in fiction that feature a female smith.
Fox News: Referenced briefly as the horrible method Gnomes get information, it looks like Burlew is taking a shot at the news outlet... until the panel cuts away to a bunch of gnomes listening to an actual fox, red, white-tipped tail, yipping noises and everything. Let's face it, if you got all your news from a small furry animal, some things would slip through the cracks.
Friendly War: We have three desert empires that always struggle against each other. However, they are secretly allied with each other. The conflict between them is merely an excuse to take over other nations, as well as a safeguard to keep the other peoples from uniting against them.