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.
Huck - Scandal
The most askew of our White Hats, Huck epitomizes the individual with "a particular set of skills" which would be difficult to describe and horrifying to list. Beyond his mental health concerns, his past record (or lack thereof) would make his file one for the record books... or possibly an urban myth to frighten baby insurance adjusters.
Jake Peralta - Brooklyn Nine-Nine
Jake's about as enthusiastic about law enforcement as they come. Like an eager puppy even. And we know what eager puppies do...
Olivia Moore - iZombie
The most ironically named hero on our list has to be "Liv" Moore, the undead medical examiner-turned-renegade-freedom-fighter. Even if insurers were willing to overlook her zombie status (and the fact her boyfriends die with worrying regularity), the fact that she initially took her M.E. job in order to have access to brains to eat will definitely mean an increase to her premiums.
Danny Reagan - Blue Bloods
Danny is the embodiment of old-school, hot-tempered policing. His multiple suspensions and questionable tactics (not to mention the number of partners and vehicles he burns through) would be major red flags for any agency offering coverage.
Angus MacGyver - MacGyver
Secret agents must have their own special brand of life and property insurance. After all, anything and everything can be burned (literally and figuratively) if you're disavowed. Mac's ability to make practically anything blow up (a side effect of learning how to diffuse bombs) might get the side-eye from typical insurers.
Linda Martin - Lucifer
Doctor, heal thyself. As the Devil's own therapist, Linda has seen A LOT over the past few years that would leave most rational people questioning their own sanity. As she continues to practice despite having had a sexual relationship with one client and being tortured by another, most agencies would probably require a psychological evaluation before signing off on her malpractice insurance.
Malcolm Reynolds - Firefly
The BIGGEST of our Big Damn Heroes but an unlikely candidate for any sort of insurance - health, home, or vehicular - considering his penchant for volunteering for lost causes and working the WORST odds... and leaving the grenades at home.
Luke Cage - Luke Cage/The Defenders
Being who he is, Luke Cage doesn't really have much use for personal health/life insurance. Third-party insurance, on the other hand, would be useful considering how much stuff he breaks. But, yeah, that's gonna be tricky considering his track record.
Raven Reyes - The 100
Suffering nerve damage, PTSD from multiple incidents, and using some A.I. hardware to speed up her brain, Raven's got a wishlist of medical needs and no indication that she'll ease up on herself to facilitate recovery. Likelihood for insurance? Slim to none.
Roger Murtaugh - Lethal Weapon
He may not be too old for this sh*t YET but he's got a whole grab-bag of risk factors pointing his way out. Heart attack, over fifty, newborn at home, high-stress job... Good thing police work comes with health benefits. Of course, they may require an updated evaluation after his exposure to Martin Riggs.
Bob Lee Swagger - Shooter
It has to be a truly messed-up dilemma to try to review an applicant like Bob Lee "the Nailer" Swagger. Ex-military (with all the physical and psychological baggage that comes with) and an expert in a job where he LITERALLY waits to shoot the person who is trying to shoot him. Huh. But does he smoke?
Jessica Jones - Jessica Jones/The Defenders
Having both superpowers and a generally f*ck-this-sh*t attitude means stuff that gets in Jessica's way gets put OUT of her way in a hurry. This could be deemed "collateral damage" but would probably be more deductible than she would care to fork out.
Tyrion Lannister - Game of Thrones
Forget insurers, bet-makers would have a field day with Tyrion's initial chances of mere survival considering his family, his penchant for drink and women, and the circumstances which should have killed him several times over and in increasingly terrible ways.
Mick Rory aka Heatwave - Legends of Tomorrow
The guy travels through time and plays with fire for a living, so the odds are not good he'll be one to score the best rates on a life insurance policy, you know?
Eve Polastri - Killing Eve
Eve has been terminated by MI-6 and picked up by a silent organization without a name. She's a spy so secret nobody knows what it is. On top of that, one of the world's best assassins is her biggest enemy. And, oh, she may not be working for the secret agency anymore, but she's still a spy. Is she in the wind? In any event, no insurance for her!