14. Samantha Smith (and Amy Gumenick) as Mary Winchester on Supernatural
The brutal murder of their mother was the root event that catapaulted brother's Dean (Jensen Ackles) and Sam (Jared Padalecki) into the isolating, depressing world of hunting demons, ghosts and otherwise spooky creatures. Yet, what they didn't know at first is that their mother basically invited her murderer to the crib that night. Flashbacks reveal that mom dukes was a hunter herself, but her family got caught up investigating the villainous Yellow-Eyed Demon and he wiped out her mother, father, even her innocent boyfriend John in one night. That's when a teenage Mary made a bargain with Mr. Yellow Eyes, which stated that if he revived John she would have ten years to live her life and then he would come calling.
We feel your desperation, Mary, but what did you think he would do when he came through in a decade? The least she could've done was try to not have kids. But, hey, it's not like she knew she'd be condemning them to a shared life with an alcholic, militant dad and then a lonely existence on the road witnessing tragedy and unable to maintain normal relationships. Sometimes it pays to think beyond the "five-year-plan."