Literature: Sinister Six Trilogy

The Sinister Six Trilogy is a series of books written by Adam Troy Castro about Spider-Man facing off against a new Sinister Six, consisting of Doctor Octopus, The Chameleon, The Vulture, Mysterio, Electro and Pity, and behind them a mysterious benefactor known as The Gentleman.

The first book, titled The Gathering of the Sinister Six is about Mysterio taking revenge against old enemies in the film industry while the Gentleman gathers the rest of the Six. Book two, Revenge of the Sinister Six, is about the Six's Day of Terror in which they try to defeat Spider-Man first one by one, then all at once. Book three, Secret of the Sinister Six, covers the Gentleman's real plan and everyone finding out about it.

The series shows examples of:

  • Ax-Crazy: Most of the Sinister Six fall under this trope, especially in the third book.
  • Badass Normal: SAFE, especially Colonel Sean Morgan.
  • Bad-Guy Bar: The Machiavelli Club, though it's more of an upscale restaurant than a bar or club.
  • Big Bad: The Gentleman, much to Doc Ock's annoyance.
  • Big Damn Heroes: SAFE arrives just in time to rescue Spider-Man and Pity from frigid North Atlantic waters after their plane crashes.
  • Brainwashed: Pity underwent years of treatment and became The Gentleman's obedient servant/assassin. She does nothing without him first ordering her to.
  • Call to Adventure: Spider-Man initially doesn't want to get involved with the suicide of Brick Johnson. Until Mysterio crashes the funeral, endangers everyone present and announces that he will be going after the film industry.
  • Continuity Nod: The story carefully fits into Marvel Comics continuity, including a Where Are They Now bit explaining what the Six's next moves were.
  • Continuity Porn: The novels contain several references to past Spider-Man stories from the the early years all the way up to the modern era. There's also several nods to past Spider-Man novels and short stories.
  • Crossover: A rather odd one at the end of the third book Pity winds up picked up by Mystery Inc of all people as she's recovering from the climax.
  • Dark Action Girl: Pity plays this one straight, being able to go toe-to-toe with Spider-Man himself.
  • Disproportionate Retribution: When Quentin Beck and Brick Johnson were both young in Hollywood trying to make names for themselves, Brick refused to help Quentin get a job. Later after becoming Mysterio, he spends a year driving Brick insane with hallucinations, ruining his career and sending him into a state of suicidal depression and seeming insanity. Then he crashes the funeral and tries to kill everyone present.
    • This is also the Gentleman's stock in trade.
  • Even Evil Has Standards: The Six with the exception of Octavius are disgusted and horrified by the Gentlemen's treatment of Pity, particularly the Vulture and Electro. The Gentleman actually calls them out on this, claiming the Six have little right to complain considering some of the things they have done.
  • Evil Laugh: Mysterio is fond of these to the point that by the second book, Spidey suspects them being played from a tape.
  • Evil Old Folks: The Gentleman, who is orchestrating the whole evil plan, is said to be at least well into his 80s.
  • Faux Affably Evil: The Gentleman.
  • Gambit Pileup: The second half of book three has the gentlemen escaping aboard his plane ready to betray everyone, except Doc Ock already worked everything out and is going to steal his plane and go ahead with his plan. Except it's not the Gentleman, it's the Chameleon who already betrayed the Gentleman and is going to do the exact same thing. Then Spidey and Pity show up because Spider-man turned her to his side so he could catch the Gentleman.
  • Good Scars, Evil Scars: Pity has scars running down her cheeks, but The Gentleman did this intentionally to make her look more helpless and nonthreatening.
  • Heroic BSOD: Spider-Man undergoes one when he gets up to the news room in the Daily Bugle and finds the butchered remains of all his friends. Luckily it was just one of Mysterio's tricks.
  • Incurable Cough of Death: Mysterio has one of these, since it's set just before "Guardian Devil" in Daredevil.
  • Karmic Death: The Gentleman who always put wealth above anything else, is killed by The Chameleon and has all of his fortune stolen from him. To rub salt in the wound, a detective whose life The Gentleman ruined confronts him as he lays dying. He thinks he has the final laugh until the detective points out he'll die a pauper. The detective then lays a penny on the opposite end of the room and leaves knowing The Gentleman will crawl for it. The icing on the cake comes after the Gentleman's death-with no friends or family to claim his body, Fiers is dumped in an unmarked grave in Pauper's Field, alone and forgotten.
  • Kick the Dog: Anytime discussion of the Gentleman's past comes up it's just an excuse for him to do this with a smile.
  • Large Ham: DON'T PRESUME TO FORGET OCTAVIUS, YOU FOOL!
  • Lightning Bruiser: Electro naturally but surprisingly Mysterio as well having extensive training as a martial arts stuntman.
  • Luke I Am Your Brother: The final book hints that Pity might be Peter's long lost sister. She isn't
  • Ninja Pirate Zombie Robot: Mysterio's robotic sharks.
  • Out-Gambitted: The Gentleman, then the Chameleon, then Doc Ock all have their master plans fail when the next person comes along.
  • Oh, Crap: The Chameleon, after betraying the Gentleman and taking his fortune when Doc Ock comes on board his escape plane.
  • Remember When You Blew Up a Sun?: Early in book 3, a minor villain named the Disk Jockey gets into a fight with Spider-man. He takes a hostage and Spider-man tells him about the 6 people trying to kill him, some of the most deadly people alive. He mentions that he's fought all of them and in their most recent Boss Rush against him, he sent them all running by mid-afternoon to get the guy to back down. Doubles as a recap.
  • Red Shirts: The SAFE troops.
  • Running Gag: A minor villain named the Candy Man shows up throughout the series. Every time he's subdued in less than a minute.
  • Screw the Rules, I Have Money!: This is about the only reason the Gentleman is a real threat.
  • Shout-Out: Many. Castro is fond of these.
  • Siblings in Crime: Gustav Fiers, aka The Gentleman, and his anarchist Professional Killer brother, Karl, aka The Finisher.
  • Sinister Silhouettes: The Machiavelli Club is designed so that everyone sits in the shadows and can't be overheard by others nearby.
  • Smug Snake: The Gentleman who is not nearly as intelligent as he thinks he is.
  • The Sociopath: The Gentleman, his brother Karl, and all the members of the Sinister Six, most notably Dr. Octopus.
  • Suddenly Sexuality: Mysterio gets lines like "I'm not, by life preference, as concientiously solicitous towards the ladies as Adrian", and describes the gay 1930s film director James Whale as an inspiration "both personally and professionally".
  • Tailor-Made Prison: In the beginning Electro is locked up in a plastic box suspended in water.
  • Villain Ball: The Gentleman quite possibly would've gotten away to enact the last part of his plan to release the catalyst over New York City had he not insisted on betraying the Six and being a dick to The Chameleon.
  • You're Insane!: Conversed and defied in Revenge over The Gentleman's treatment of Pity:
    Spider-man: You're insane!
    The Gentleman: Not at all. Simply evil. Those of you who happen to be players on the other side have so much trouble understanding the difference.