Enemies
- The Box (featured) - An insane cyborg vigilante character and a possible future son of Jack-in-the-Box II, an alternate version of the Jackson and Jerome Johnson.
- The Brass Monkey (featured) - a living metallic simian statue with a human mind.
- The Deacon - Head of the crime families of Astro City; despite years of investigation, has never been convicted of any crime.
- "Eyes" Eisenstein (viewpoint) - a small-time crook who discovers Jack-in-the-Box II's secret identity, but flees town when paranoid fantasies of what may happen if he told anyone get the better of him.
- The Gorilla Troops - henchmen of the Brass Monkey who wear gorilla masks.
- The Human Weasel - a short, wiry villain with weasel-like physical characteristics. His status as a Jack-in-the-Box villain inspired by the lyrics of Pop Goes the Weasel.
- The Jackson (featured) - A fanatic feral vigilante and a possible future son of Jack-in-the-Box II, an alternate version of the Box and Jerome Johnson.
- The Junkman (viewpoint) — an aged villain seeking vengeance on society for age discrimination. Recycles and enhances his weaponry from discarded trash. His closest analog, interestingly, is his primary antagonist, Jack-in-the-Box, whose origin, inventive genius, and use of gimmicks parallel his.
- The Middleman - a smuggler and gunrunner specializing in acquiring the weaponry of defeated villains and fencing them to other villains.
- Prospero - a past opponent of Jack-in-the-Box II, currently incarcerated.
- Smoke & Mirrors - villain with illusion-casting powers, a past opponent of Jack-in-the-Box II; as a hireling of the Conquistador, created an illusion of a city-wide conflagration. Currently incarcerated.
- The Underlord - a past opponent of Jack-in-the-Box I and II, active in the 1980s.
- Steeljack (viewpoint) - a past opponent of Jack-in-the-Box I, active in the 1970s, since reformed. As a super-villain he was a member of the Terrifying Three. After serving his time he was tapped by former associates as a private investigator to solve a string of murders in the super-villain community.
Read more about this topic: Jack-in-the-Box (Astro City)
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