History Literature / TheRulesOfSupervillainy

* {{Antihero}}: Gary zig-zags between this and VillainProtagonist for much of the book before finally choosing which he is. [[spoiler: He's an anti-villain.]]

* {{Antivillain}}: Namechecked. Gary says this is what he aspires to be after a long period of soul searching.

* CaptainErsatz: Necromongers are not just {{Expy}} of the creature from ''Franchise/{{Alien}}'' but actually the inspiration for them in-universe.

* {{Clocktower}}: The Nightwalker was based in the Falconcrest City Clock Tower.

* NinetiesAntihero: The book shreds these mercilessly (no pun intended). Shoot-Em-Up is the first and he inspired Gary to become a supervillain by murdering his brother after he reformed. The Extreme, an entire team of them, are even worse.

* {{Transgender}}: The Human Tank is a trans woman. She's also TheAtoner for her past as a supervillain and now a superheroine.

* BadassGay: The book has a number of gay and bisexual superhero and supervillain characters. These include the protagonist's wife, his henchwoman, his wife's ex-girlfriend (one of the strongest supervillains alive), and a Fragile Speedster who is married to an even more famous and powerful Speedster.

* {{Adorkable}}: Lampshaded in-universe as one of Gary's qualities by all of the people who know him.

This book contains the following tropes:

* FreudianExcuse: Played with. The death of Gary's brother and the traumatic consequences [[spoiler: including killing his brother's murderer at age fourteen]], certainly contributed to Gary becoming a supervillain. However, it's also clear Gary always admired supervillainy and had extremist political vies as well.

** Ultragoddess is one for Supergirl w/ Green Lanterns powers and the Shadow Seven are stand-ins for the Suicide Squad.

* {{Transsexual}}: The Human Tank is a male-to-female one. She's also TheAtoner for her past as a supervillain and now a superheroine.

** When Cloak debates Gary's claim that an AntiVillain is a thing, Gary argues that he looked it up on [[ThisVeryWiki TVTropes.]]

The sequel, ''Literature/TheGamesOfSupervillainy'' came out on December 19th, 2015.

* MsFanservice: Cindy Wakowski a.k.a. Red Riding Hood deliberately cultivates this role as a henchperson.

* PopCulturedBadass: A very very nerdy pop-cultured badass.

* Tradesnark: Gary is ''Merciless: The Supervillain without Mercy™.

* VillainDecay: In-universe. Diabloman used to be one of the most feared villains in the world but health problems have reduced him to being a D-Lister's sidekick. Gary offers him a position as his Dragon and Diabloman never looks back.

* CoolBase: The Nightwalker was based in the Falconcrest City Clock Tower.

* TheAdjectivalSuperhero: ''Merciless: The Supervillain without Mercy!"

* AmbiguouslyBi: Cindy. Humorous, since Gary's wife Mandy is openly bisexual and put off by Cindy's vague allusions.
* AmbiguousDisorder: Gary reacts to things in a slightly off-way, finding humor in inappropriate things as well as saying whatever is on his mind regardless of whether it's appropriate or not. He also suffers no guilt for killing supervillains. This briefly leads him to think he's a Sociopath. Given he's prone to empathizing with everyone ''except'' the supervillains he kills, this is unlikely.

* DarkChick: Cindy fills this role in most of the supervillain teams she's on. Also qualifies as a NotSoHarmless villain when she reveals she's closer to TheLancer of the group.

* DeadpanSnarker: Gary is this in ''spades.'' Almost every word out of his mouth is unaudulterated pure sardonicism.
** Qualifies as a full-on SnarkKnight once you realize Gary's opinion of himself isn't much higher than his opinion of anyone else. Mandy, Ultragod, Diabloman, and Ultragoddess are about the only people he seems to respect.

* GenreSavvy: This is why Gary is able to get out of the majority of his predicaments along with the variety of powers he gets from the Nightwalker's cloak. Qualifies as DangerouslyGenreSavvy since he's a supervillain.
* GrayAndGrayMorality: Gary's conflict with the Society of Superheroes is this as he's clearly in the wrong but they're a little too repressive for their own good.
* HappilyMarried: A first in superhero literature as both Gary and Mandy seem to be quite content in their relationship.
* HollywoodNerd: Gary is an enormous geek who references everything from Star Wars to video games to comic books.
* IntelligenceEqualsIsolation: It's implied Gary suffered this as a child, reading much-more advanced books than is normal for his age while hanging around his supervillain brother instead of kids his age.
* JackOfAllTrades: Gary has a number of minor (by comparison to the setting) abilities. Minor fire, ice, levitation (not flight), durability (not invulnerability), and insubstantibility powers. He can also see ghosts. Gary turns these all into a massive advantage.
** Subverted when he [[spoiler: makes a pact with Death]] and becomes a master of fire and ice throwing.
* JewishAndNerdy: Gary is a definite example of this. Cindy is definitely Jewish and UN-Nerdy.

* KavorkaMan: Gary is an unemployed oddball who wants to be a supervillain. No less than three stunningly attractive women have been revealed to have been in relationships with him. He's also off-handedly mentioned to be with many more.
** Played with when Gary reveals the secret of his success with women was to treat all of the ones he wants to date with respect while giving complete honesty about his intentions. [[WordOfGod It helps the author has also said Gary bears a striking resemlance to]] [[ComicBookFantasyCasting Wentworth Miller.]]

* RidiculouslyAverageGuy: Gary appears to be this but turns out to have a startling number of relationships to many superheroes and villain.
* SoapboxSadie: Gary has elements of this, talking at great length about political matters which all the other characters tune out as background noise.

''The Rules of Supervillainy'' is the first book in the ''Literature/TheSupervillainySaga'' series by Creator/CTPhipps. The series is published by Jim Bernheimer, author of ''Literature/ConfessionsOfADListSupervillain.''

''The Rules of Supervillainy'' is the first book in the ''Literature/SupervillainySaga'' series by Creator/CTPhipps. The series is published by Jim Bernheimer, author of ''Literature/ConfessionsOfADListSupervillain.''

''The Rules of Supervillainy'' is the first book in the ''Supervillainy'' series by Creator/CTPhipps. The series is published by Jim Bernheimer, author of ''Literature/ConfessionsOfADListSupervillain.''

** The Nightwalker is one for Batman as the Society of Superheroes reflects archetypes of the Justice League (Ultragod for Superman, Guinevere for Wonder Woman, Prismatic Commando for Captain America).

* SoapboxSaddie: Gary has elements of this, talking at great length about political matters which all the other characters tune out as background noise.

* NiceJobBreakingItHero: Not Gary but Shoot-Em-Up. An Anti-hero in the Nineties who wanted to kill supervillains to make sure they stopped menacing people, targeted a bunch of reformed and mostly-harmless ones in front of their families. The effect of this is, after killing Gary's brother Keith (a B-list supervillain named Stingray), he sets Gary on his path to supervillaindom. [[spoiler: Which results in Gary shooting him in a hotel later that year, despite being only fourteen years old.]]

** A blink and you'll miss it reference is Gary's fourteen year old self is described as dressing nearly identical to Quentin Quire.

* CompositeCharacter: The book combines this with {{Expy}} to create very familiar-seeming but unique characters.
** The Nightwalker seems to be a combination of Batman and Doctor Strange.
** Ultragod is a combination of the Silver Age Superman, Icon, and Green Lantern.
** Ultragoddess is, appropriately, one for Supergirl with the same Green Lantern-esque powers as Ultragod.
** Red Riding Hood seems to be a stand-in for Harley Quinn and Songbird.
** Diabloman stands in for Bane, the Tattooed Man, and Brother Blood with elements of Deathstroke. He's also similar to Deadshot in that he has young daughter he cares about deeply.
** The Lightning Family are very similar to the Flashes.
** Stingray is a Stand-in for Black Manta and belongs to a group similar to the Flash's Rogues.
** The Extreme seem to be a combination of X-Force, Youngblood, and every other 90s group ever with a healthy TakeThat toward them.
** Tom Terror resembles the Golden Age Lex Luthor combined with Doctor Sivanna and the Red Skull.
** Gary is inspired by Spiderman, Anarky, and the Hood. He also has elements of Batman in his origins.

** Red Riding Hood seems to be a stand-in for Harley Quinn.