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  • Complete Monster:
    • Darryl "Fearmaster" King, when not ordering the demolition of inhabited neighborhoods and overseeing experimentation on the downtrodden as a part of his day job as a senior executive of Alchemax Corporation, Fearmaster acts as the head of the Cyber-Nostra, and uses his transformative powers on innocent women, disfiguring some and turning others into decorative statues for his amusement. While he also used his abilities to revitalize those who attended his church, he had the rejuvenations be only temporary so that his congregation would become addicted to them and give him anything in exchange for them, including sex. Fearmaster's contempt for everyone around him also extended to his own allies; when the criminals that the Punisher had locked in his basement begged Fearmaster to let them out, the latter ignored them, and referred to the prospect of them all starving to death as a "bonus".
    • Kron Stone is the 2099 incarnation of Venom, the son of the equally-sociopathic Alchemax executive Tyler Stone, and a monster who plays a role in the origins of both the 2099 Punisher and the 2099 Spider-Man. Twisted since he was a kid, Kron was guilty of attempted murder in his youth, and graduated to slaughtering entire families at a time, even the kids, punishing random innocents to vent frustration about his own unhappy childhood. When put down by the Punisher, Jake Gallows—whose entire family Kron considered cheaper than one of his suits—Kron barely survived and bonded to the Venom symbiote, killing a random bum to disguise the corpse as his own. Taking the mantle of Venom, Kron attacked a hospital and attempted to kill his comatose father, killing dozens of innocents in the process, and takes the life of Miguel O'Hara's ex-lover Dana after forcing Miguel into a Sadistic Choice involving Dana's life and his other girlfriend, Xina. Both Jake and Miguel reject Kron's attempt to foist all the blame for his evil on his troubled childhood, and beneath his excuses Kron is a savage who kills because he loves it.
  • Crazy Is Cool: A frequent occurance, an example being when an evil shaman claims that death will allow him to ascend to Godhood. The Punisher sabotages this by dramatically feeding the man to a particle accelerator, which will supposedly incinerate his spirit.
    Punisher: ... I'm gonna get me a gun that shoots souls to death!
  • Designated Evil: After Jake becomes director of SHIELD, he eventually employs technology designed to track thoughts to detect malicious intent, so they can stop crimes before they happen. This is treated as a sign of how far Jake has gone over the edge, and it is the kind of thing you'd see in a lot of dystopia fiction. The problem is, the only times we see it being used are on people who were very clearly about to commit murder. Instead of coming off as a horrible device that will cause people to be arrested for having nasty thoughts, it instead comes off as an effective way to prevent serious crimes.
  • It's the Same, Now It Sucks!: Some readers criticized the book because, compared with 2099's takes on Spider-Man or Ghost Rider, Punisher 2099 really wasn't that distinct from the mainstream Punisher, apart from more high-tech weaponry and maybe a bigger focus on the class dynamics of the 2099 world.
  • Hilarious in Hindsight: Mills had previously written a dark, biting satire of The Punisher in Marshal Law. Ten years later, he wrote his own The Punisher story.
  • Memetic Mutation: A number of Jake's deranged declarations, especially, "I don't need a jet pack — all I need is hate!"
  • So Bad, It's Good: They combined The Punisher with Judge Dredd (which Pat Mills also helped create) and made it as over-the-top gritty as possible.

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