The Winchester Family Business

 

Let's face it, if I didn't have a catch all category for all the demons that played their part in the grand scheme of freeing Lucifer, a chunk of this list would be taken by them. What fun would that be? Powerful, scary demons though are what drives this show and they must get their due. You have to admit, by freeing that space up, the list has had a few surprises, right?

 

Players involved in a well organized and carefully executed plan are worthy of taking the number one spot. When the opposition decided they weren't going to try and stop them either, even providing a little help, how could they fail? 

 

So we'll start with the biggest baddie of all. Azazel's name wasn't even known until "Sin City." Until then, he was just the yellow-eyed demon. From the pilot though we knew he was one nasty nemesis. He's been played by a multitude of actors, even Jeffrey Dean Morgan, and each time the dude becomes creepier and more vile. There has never been any ambiguity with Azazel. This fallen angel is eeeeevillll! He flambéed both Mrs. Winchester and the potential Mrs. Winchester, cursed poor Sammy for life, and offered up his boss a bloodied “bag full of nuns.” He even took John Winchester's life although John did ask for that. Azazel would have done it anyway. 

 

Azazel turned out to be the one with the master plan, and his unforeseen demise at the hands of Dean didn't do anything to stop that plan from going forward. Demons are a rather patient lot, and what Azazel put into place in demon time was hundreds of years in the making. Death of the key player wasn't going to stop them, and neither was the reluctance of the sole surviving "child." The demonic creed seems to be "When there's a will there's a way."

 

So, enter Ruby. Her role cannot be denied, despite how many didn't care for her.    She's hardly a mastermind, but definitely a brilliant manipulator. So what’s the best way to get the attention of the chosen one who refuses to step up to his destiny? Save his life?   Not enough. Promise to help him save his brother from impending doom? Closer. Still not enough though since she didn’t. So, once brother is out of the way, how about trying to be a sympathetic friend and mentor? Then lover. Yeah, that worked. 

 

Her patience in earning Sam's trust, even to the behest of Dean, coming in after Azazel's death to finish what he started cemented her claim that she is indeed "awesome." Even she was floored that her plan worked. At least she had a couple minutes of joy before Dean gutted her like a fish.

 

Alastair sits on the other end, the reluctant participant who surfaced out of duty.   He was only terrifying though when he was Christopher Heyderdahl. As I said in my review of "Heaven and Hell," Mark Rolston tried to do Alastair like Marlon Brando, but ended up more like Daffy Duck. He certainly didn't scare me all that much, and if anything earned some gratitude for carving up Ruby. 

 

Alastair gets major kudos as a true antagonist because Christopher Heyerdahl is that good. Any villain that makes the hair on the back of my neck stand on end and turn my stomach into knots ranks very high in my book. I don't turn so easily. Sure, his obvious masterpiece was "On The Head Of A Pin," a performance that’s more incredible given the fact he was chained up most of the episode yet still evoked full-on hebegeebees. Then he managed to get the same reaction out of me with his less than two minute appearance in "When The Levee Breaks." Easily the best acting I’ve seen from a guest actor portraying the villain. 

 

Ah, but it's Alastair's death that's one of the most jaw-dropping, "Hell Yeah!" moments of the series. After Sam interrogates him with his mind grip of demon terror, Alastair is none too relieved to get sent back to Hell. After all, he's made it known on more than one occasion that he'd rather be doing what he loves the most, carving up souls on the rack in Hell. Sam's not going to let him off the hook though and with evil grin of his own announces, "I'm stronger than that now. Now I can kill." Alastair sparks, fries, and dies and the completely stunned expression on his lifeless shell pretty much sums it up for all of us. What the hell just happened?
 

But let’s not forget Meg, the first badass demon to surface. She was sassy, smart, sexy, and didn't care for the Winchesters too much. She especially hated John, but just like Sam and Dean, wasn't allowed to kill him. A greater plan was involved. Meg had to fight to restrain her homicidal tendencies toward Winchesters and showed loyalty to her "father" until it got her sent back to Hell. As soon as she busted out, her loyalty burned away and she went after revenge against the brothers by possessing Sam, no longer giving a "rats ass" to the master plan. Unlike the others, she didn’t meet a grizzly end, and is still out there ready to strike at any moment. With Lucifer free, that sets up a nice possibility of exploring what happens to demons who failed loyalty. Or, it could amount to nothing. We'll see. 

 

 

Then there's Lilith, who's not on this list. An upcoming segment will explain why.

 

There you have it! Another top ten done. This list likely went places few expected, and that makes me happy. Tell me where I'm right, where I'm wrong, and who I missed. If you don't I'll forget that these lists are subjective and I'm not the all powerful authority on such things. Coming up next is a small bonus, the top five worst antagonists. I promise it’ll be in one article. I don’t want to waste too much space on the unworthy.      

Top Ten Supernatural Antagonists - #2
Top Ten Supernatural Antagonists - #3
Top Ten Supernatural Antagonists - #4
Top Ten Supernatural Antagonists - #5
Top Ten Supernatural Antagonists - #6
Top Ten Supernatural Antagonists - #7
Top Ten Supernatural Antagonists - #8 and 9
Top Ten Supernatural Antagonists - #10