All of us can relate the pain in the butt getting insurance can be but how much worse would it be when you disclose spending your spare time "not failing" the city as a masked vigilante?
What would the rate hike be if it were known you'd EATEN the brains of your last dozen (albeit already dead) clients?
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How fast would the agent rush you out the door if your face had been all over the news for an alleged violent crime spree? Could you even get in the door?
As a doctor, what kind of malpractice insurance would cover you if you hung your shingle in a city full of escaped insane asylum inmates?
Fair enough, it's unlikely that vampires, zombies, or Lannisters would be looking for insurance but imagining those application interviews makes for guaranteed hilarity!
Oliver Queen - Arrow
You'd think coming back from being presumed dead for five years would give your creditors some confidence in you but, since coming back, Oliver's been shot at, shot up, blown up, elected mayor, and sent to prison. That's a lot of risk right there.
Raylan Givens - Justified
Yes, being a U.S. Marshal means a certain amount of gunplay but Raylan's WAY up on that bell curve. An outlier even in Harlan County.
Dr. Lee Thompkins - Gotham
Once a reliable bet despite a risky posting at Arkham Asylum, our good Doctor Thompkins has seen her assurance drop through the basement of Indian Hill since exposing herself to the Tetch Virus, crowning herself Queen of the Gotham Narrows, and (um, oh yeah) DYING.
Jack Harkness - Doctor Who/Torchwood
He dies A LOT so yeah, there's no way anyone's gonna cover his deductible.
Cassidy - Preacher
Being technically undead AND liable to burst into flames in sunlight, there's a lot of pre-existing conditions that this eternal wingman vampire would probably have difficulty getting past his H.M.O.
Kara Danvers - Supergirl
As Kara Danvers, personal assistant and reporter, she's been unreliable at times and somewhat accident-prone. As Supergirl, she saves people on a regular basis but not without causing some infrastructure damage (like the Otto Binder Bridge incident) which most insurers would find more liability than they'd be comfortable with covering.