#5 - Anna Milton
So what makes Anna a reluctant and unwilling hero? She was an almightly and powerful angel and gave it all up. She lost faith, got disillusioned, and decided to pursue human pleasure. Worse, she even threw her grace down to Kentucky, the one state that had no idea what to do with it other than grow a tree.
Anna fits in this category because she’s the first to realize something was rotten in Heaven and did something about it that didn’t involve starting the apocalypse or becoming a Lucifer worshipper. She is a silent rebel that’s determined to fight on the side of good, despite the knowledge her “father” wants her dead. She’s trusting her instincts. Granted that involves a lot of hiding and pleading to Castiel to do better, but she did save his life (twice) and rid the Universe of a very bad demon (sort of) and a very bad angel. Plus she nails a Winchester, in the back seat of the Impala nonetheless, just for fun. 
Alas, her soft spot for Castiel gets her captured, but she’s proven right when Zachariah reveals the dastardly plan. This is enough for Castiel to come to his senses, which is no easy feat. Something tells me there will be more to come from her too now that the world is ending. Castiel needs a fallen friend. 

Anna:The end... Is coming. The apocalypse.
Psychologist: The apocalypse. Like in the bible?
Anna: Kind of. I mean, same bottom line. This demon, Lilith, is trying to break the 66 seals to free Lucifer from hell. Lucifer...Will bring the apocalypse.  So...Smoke 'em if you got 'em.
"The Father you love, you think He wants this? You think He’d ask this of you? You think this is righteous? What you’re feeling, it’s called doubt. These orders are wrong and you know it. But you can do the right thing. You’re afraid, Cas. I was too. But, together we can.”
Uriel: You haven’t even met the man! There is no will. [punches Castiel] No wrath. [punches Castiel] No God.
Anna: [stabs Uriel through the neck from behind] Maybe. Maybe not. But there’s still me.

#4 - Victor Hendriksen
Even when he’s hunting down Winchesters, you could hardly call FBI Agent Victor Hendriksen a bad guy. He honestly believes he’s fighting on the side of justice, saving the world from two very bad men. After all, that’s what he’s been trained to do.   
He’s a righteous son of a bitch, but that’s part of his charm. His tactics and delivery are cool, cavalier, and we knew that it would only be a matter of time before he would become an ally. Sure he learns the hard way, being possessed as demons surround the same jailhouse he compares to “Mayberry PD,” but luckily the same fugitives he’s hunted as wackos are crazy enough to use a toilet to get the damned thing out of him. Whatever works. 
Unfortunately, we also knew given the history of this show it wouldn’t be long before he joined the dead pool too. He goes out swinging and knowing the truth though, which is the heroic way to go in this show. He even gets to come back as an angry spirit, so we truly haven’t seen the last of him. Death doesn’t seem to be an issue on this show. 

Dean: Yeah, listen, I'm not really in the negotiating mood right now.
Hendricksen: Good. Me neither. It's my job to bring you in; alive's a bonus but not necessary.
Dean: Whoa. Kinda harsh for a Federal Agent, don't you think?
Hendriksen: Well, you're not the typical suspect, are you, Dean? I want you and Sam out here, unarmed. Or we come in. And yes, I know about Sam. Bonnie to your Clyde.
Dean: Yeah, well, that part's true, but how'd you even know we were here?
Hendriksen: Go screw yourself, that's how I knew. It's become my job to know about you, Dean. I've been looking for you for weeks now. I know about the murder in St. Louis, I know about the Houdini act you pulled in Baltimore. I know about the desecrations and the thefts. I know about your dad.
Dean: Hey, you don't know crap about my dad.
Hendriksen: Ex-marine, raised his kids on the road, cheap motels, backwoods cabins. Real paramilitary survivalist type. I just can't get a handle on what type of whacko he was. White supremacist, Timmy McVeigh, to-may-to, to-mah-to. Dean: You got no right talking about my dad like that. He was a hero.  
“My job is boring. It's frustrating. You work three years for one break, and then maybe you can save a few people, maybe. That's the payoff. I've been busting my ass for 15 years and nailed a handful of guys and all this while there's been something off in the corner so big. So yeah, sign me up for that big frosty mug of waste of my damn life."
#3 - Chuck The Prophet
Why is Chuck so high? He’s a prophet for God’s sake! An ordinary, average sad sack loser who was chosen by someone high above (maybe even God himself) to see and write the all important story of “The new New Testament.” He’s instantly earned protection from an archangel and can’t even kill himself, for angels have that covered too. 
Oh, but poor Chuck. He’s a loveable guy that didn’t take the news of his holy destiny very well. Who would though? I mean, what happens when you write an entire series of novels on fictional brothers saving the world only to have them show up on your doorstep one day? What do you do when you end up writing yourself into the story because you see it during your “process,” but omit pertinent details like one brother drinking demon blood to make him look less sympathetic and to leave out the fact you’re a prophet to avoid “M. Night” level of douchiness?
It’s all a bit too much for Chuck, who when called upon to perform heroics balks at it entirely. Eventually he caves to intimidation by Dean. He does save the day though, so no matter how he’s pushed, he scores big. He’s far less reluctant when asked to give the location of Sam in the finale, probably because he knows the end is coming. His attempt to order a night with 20 high priced hookers lets on he knows something we don’t. In the face of danger though, he stands beside Castiel in solidarity against the archangel, even if Castiel doesn’t care for the shoulder grab. Angels are so damned touchy!  

"Look, uh, I appreciate your enthusiasm. Really, I do. It's always nice to hear from a fan. But for your own good I strongly suggest you get a life."
Chuck: Oh. wow. Wow. That sounds...moist. Uh, what are your rates?
Woman: (on the phone): We can get you one girl, one hour -- $1,000.
Chuck: Okay. Then, uh, I'll take 20 girls for the whole night.
Woman: Um, sir, I'm not sure you can afford that.
Chuck: Lady, sometimes you got to live like there's no tomorrow.
#2 - Ellen Harvelle
Let’s face it, women don’t look good on this show. They’re skanks, whores, bitches, poorly acted, not strong, and none can be good enough for a Winchester. Most of the time when a female character is introduced, hoards of fans band together in one common goal, to break her down. That didn’t happen with Ellen Harvelle. Fans hated the Roadhouse, hated Jo, were torn on Ash, but Ellen won them over. Her tough as nails resolve made her different. Yet she isn’t perfect, as best shown in her strained relationship with her daughter Jo. The life definitely has its complications on all sorts of families. 
Ellen is the wife of a hunter, one who died, and learned long ago everyone doesn’t have to be alone in this fight. She stayed home and raised a daughter in a world where she knew horrible things existed, but never let them lose hope. They would go on fighting. She dedicated herself to supporting those that continued the fight, whether it be providing information or giving them an inviting place to let loose after a long hunt. 
Ellen never turns a blind eye to anything and isn’t afraid to seek the truth. She demands to know about Sam’s psychic visions, realizing there is far more at stake than Sam’s feelings about being a freak. She is there to help though and knows the importance of family, no matter what the reasons. Even though Sam asks her to not reveal where he’s going in “Hunted” she tells Dean where he is anyway, for there’s nothing more important than family. When it comes to Jo though, she gives up. She tells Jo she can’t hunt while under her roof, thus forcing her to leave. It’s not unlike what John Winchester did to Sam and goes to show parenting under these circumstances isn’t easy for anyone.     
“This isn't just your war, this is war. Now, something big and bad's coming and it's coming fast, and their side holds all the cards. Now, at best all we got is us. Together. No secrets or half-truths here.”
Dean: Hey, have you heard from Sam?
Ellen: I have, but he made me promise not to tell you where he is.
Dean: Come on, Ellen, please. Something bad could be going on here, and I swore I'd look after that kid.
 Ellen: Now Dean, they say you can't protect your loved ones forever.
(beat) Well, I say screw that. What else is family for? He's in Lafayette, Indiana.

#1 - Bobby Singer
You know, in the COUNTLESS articles I’ve written on this site (and elle2 as well), there hasn’t been anything that has paid a decent homage to the strong iron anchor in the Winchester’s lives. The one that holds everything together despite him being stretched so thin that it’s a miracle he never lets go. He’s a fighter, a mentor, a survivor, a subject matter expert, and he does amazing things when he has the weekend off. 
Let’s face it, as much as we love Bobby, he’s a slob. He has a house the size of a cathedral, but it’s littered with piles of books, papers, artifacts, and big bedrooms upstairs that don’t hold beds for his guests. His backyard is a classic car graveyard and even his dependable Chevelle, a true American classic, is a multi-colored junker. Somehow though, his lack of attention in his personal life doesn’t apply to his hunting. We accept his overlooking of those trivial things so he can focus on the bigger picture. You know, saving the world while he looks out for a pair of heroic brothers that never got that kind of devotion from their father.   
The hunting life, just like with other hunters, found Bobby through tragedy. A demon possessed his wife and he killed her without knowing what was really wrong. From that point forward, he dug into the life, learning all he could through research and understanding lore. A simple junk dealer in South Dakota became the librarian of the netherworld and an invaluable resource to those out there in the wilderness with no clue what they’re up against. Oh, but with that knowledge also came guts, for showing fear and hesitation won’t assure long term survival. No, he’s not growing old gracefully, but he is growing old.  
He cares more about Dean and Sam that anyone ever has. â€œIdgit” in his language is deep concern and he is there when both Sam and Dean die, forced to endure that pain of losing them. He turns to alcohol when Dean dies when he's left alone by a devastated Sam. Dean’s new chance becomes Bobby’s as well, and along with sobriety comes a new found responsibility to save the world. He doesn’t react to the presence of angels with disbelief and awe. He takes it like he does with everything else, with acceptance and the flexibility to change with the rules. 
He’s always respected the brothers enough to make their own decisions though, no matter whether he agrees with them or not. Sure, there are times he gives them the what for, like when they try to leave him behind in “No Rest For The Wicked” or when he tries to get Dean to show a little mercy to Sam in “When The Levee Breaks,” but he knows not to push too hard when their minds are made up. He's all to familiar with the stubbornness of a Winchester. 
Supporting the heroes is often more heroic, for the supporter has to stick with these conflicted beings and all their mistakes through thick and thin, covering their backs and rescuing them from themselves at times. Bobby especially has a heavy task, for he also has to step in when each brother doesn’t see eye to eye and do all he can to guide them toward even ground. He can only do so much though and is there for the fallout as well. He never gives up, and that right there is the best definition possible of the unsung hero. 

Bobby: You stupid ass! What did you do? What did you do?! [He pushes DEAN.] You made a deal...For Sam, didn't you? How long did they give you?
Dean: Bobby.
Bobby: How long?!
Dean: One year.
Bobby: Damn it, Dean.
Dean: Which is why we gotta find this yellow-eyed son of a bitch. That's why I'm gonna kill him myself. I got nothing to lose now, right?
Bobby: [He grabs DEAN by the collar] I could throttle you!
Dean: And send me downstairs ahead of schedule?
Bobby: [He lets go of DEAN] What is it with you Winchesters, huh? You, your dad. You're both just itching to throw yourselfs down the pit.
Dean: That's my point. Dad brought me back, Bobby. I'm not even supposed to be here. At least this way, something good could come out of it, you know? It's like my life could mean something.
Bobby: What? And it didn't before?! Have you got that low of an opinion of yourself? Are you that screwed in the head?! [He grabs Dean again]
Dean: [Choking up] I couldn't let him die, Bobby. I couldn't. He's my brother.
Bobby: How's your brother gonna feel when he knows your going to hell? How'd you feel when you knew your dad went for you?
Dean: You can't tell him. You can take a shot at me. Whatever you got to do, but please don't tell him.
[Bobby begins to cry, grabbing Dean's chin.]
“Fat, drunk and stupid is no way to go through life, son.”
Bobby: Well, you got just over five hours to go. You're piercing the veil, Dean, glimpsing the "B" side.
Dean:  Little less New Agey, please.
Bobby: You're almost hell's bitch, so you can see hell's other bitches.
Dean:  Thank you.
Bobby:  Do I look like a ditchable prom-date to you?
Sam:  No Bobby. Of course not.
Dean:  This is about me... and Sam. Ok? This isn't your fight.
Bobby:  The hell it isn't! Family don't end with blood, boy. Besides, you need me.
Dean:  Bobby.
Bobby:  You're playing wounded. Tell me, how many hallucinations have you had so far?
Dean:  How'd you know?
Bobby:  Because that's what happens when you've got hellhounds on your butt. And because I'm smart.
Sam: You built a panic room??
Bobby: I had a weekend off.
Dean:  Bobby, you're awesome.
“If you're going to shoot, shoot! Don't talk!”
Dean:  How long's this going to go on?
Bobby:  Hang on, let me look it up in my demon detox manual. Oh wait. No-one ever wrote one. No telling how long it will take. Or even if Sam will survive this.
“You stupid, stupid, son of a bitch. Well boo-hooo I am so sorry your feelings are hurt – Princess. Are you under the impression that families are supposed to make you feel good? Make you an apple pie maybe? They're supposed to make you miserable! That's why they're family.”