To paraphrase a much memed quote from “Gilmore Girls,” “Supernatural” isn’t a just a television show, it’s a lifestyle. After over 220 episodes, jars of man-tears, thousands of one-liners and sublimely dark comedy, “Supernatural” is still breaking our hearts in new and excruciating ways.
It all began on November 2, 1983 when a demon bled into baby Sammy’s mouth (grooming him to lead the underworld, as you do) and ended up killing his protective mother, Mary, sending John Winchester and his then young sons on a lifelong quest to find her murderer and save people along the way.
In the Catholic church, November 2 is All Soul’s Day—a time to honor the dead. After hours of sorting, debating and touch of hysterical weeping, I've selected "Supernatural's" 11 Saddest Moments. Spoiler Alert!: Most of them include dead people!
11. Dean warns young Mary. Castiel sends Dean (Jensen Ackles) back in time to learn some heavy and important information about his family, mainly that his mother was raised as a hunter and the reason the demon Azazel came for Sam as a baby was due to a deal they had made a decade before. “In The Beginning” is the masterfully acted episode that should have earned Jensen Ackles his first Emmy nomination for his work as Dean Winchester. Try not to wibble when a choked up son begs his clueless mother to not to get out of bed on 10 years in the future in the clip above.
10. Sam surrenders. It’s a gargantuan understatement to say that Sam Winchester (Jared Padalecki) has suffered. But even this fighter reaches the end of his rope after suffering for months from horrendous hallucinations and insomnia as a result of being possessed by Lucifer. It's even more gutting that Sam spends his last lucid moments fighting for someone else.
9. Sam’s world crashes and burns. “Supernatural’s” trailblazing angst-fest began in the very first episode when Sam’s normal and safe world goes up in flames, starting with his hot girlfriend, Jessica (puns totally intended). The “Supernatural” writers have sparingly poked that wound a couple more times since by having Jessica (Adrianne Palicki) return in Dean’s Djinn-dream “What Is And What Should Never Be” and even worse, as a mask of the devil himself in “Free To Be You And Me.”
8. Dean throws the Samulet away. The Brothers Winchester have deeply hurt each other over the years. There have been angel-tainted voicemails, (badass) physical fights and enough lies between them to fill Baby’s bottomless trunk. However, few moments trump an overwhelmed and heartbroken Dean angrily disposes of the amulet Sam gave him for Christmas—a gift he cherished for more than 20 years. The impetus for Dean doing so was probably due to powerful angelic manipulation trying to tear the brothers apart. It still left fans screaming at the television and campaigning for the amulet's return ever since.
7. Sam’s doomed love life. It’s a running gag that Sam’s romantic life is doomed, and that joke began with the terrible scene in which Sam—who lost his girlfriend—finally opens his heart to fall for another girl--only to discover that she is a heart-munching werewolf. Even worse, she asks Sam to kill her to prevent her from hurting anyone else. As bonkers as it sounds, Jared Padalecki and Jensen Ackles expertly turn these extraordinary moments into real and agonizing struggles.
6. Dean’s breakdown. Dean is known for channeling all of his angst into one perfect tear that is so epic, it even been immortalized in song in "Supernatural's" 200th episode. So in season 4's "Heaven and Hell" when Dean finally speaks about the torture he received and inflicted in hell in a with a full tilt pretty-cry, it felt like a machete to the feels. Grab a tissue and watch the clip above.
5. Ellen and Jo Harvelle, badasses ‘til the end. You cannot wage a battle for good and evil without losing some good soldiers along with the way. Ellen and her daughter, Jo, were not just soldiers, they were family. Ellen acted as a surrogate mother to the boys and Jo was a friend to Sam and possibly more to Dean. They died on a failed mission to kill the devil, but made sure to take out a few hellhounds with them. Their deaths were brutal, tragic and I’m still not over them.
4. Sam and Dean first deaths. I could almost fill this countdown solely with Sam and Dean’s deaths, but nothing hurts more than the first time (though Dean's last death in the season 9 finale still stings). Also, their demises were all apart of a massive, ingenious endgame decades in the making. Sam’s death caused a distraught Dean to sell his soul. Dean’s bloody death a year later forced Sam to use his demonic powers to fight demons While in hell, Dean unknowingly kick-started the apocalypse. Sam’s mastery of his powers helped him release the devil at the end of season 4 and sent him back to the cage at the end of season 5. When death is the best case scenario, you know you're you're dealing with a deliciously morose show.
3. Sam comes clean in “Sacrifice.” Sometimes, the best way to inflict pain is with brutal honesty. In “Supernatural’s” season 8 finale, the frustratingly quiet Sam Winchester finally unleashed years of fraternal turmoil over being regarded as the lesser Winchester, and he was ready to die to prove his worth to his big brother (and for the greater good). It was a long overdue moment for Sam Winchester, and one that helped clear decades of tension between the brothers. Watch the clip above. The ending, in which Sam collapses and angels fall from Heaven, is a chilling and tragic bonus.
2. Bobby’s last memory. On “Supernatural,” dying is almost a rite of passage. The death of Sam and Dean’s surrogate father was traumatizing, but not totally unexpected. What sent me adrift in a sea of my own tears was the memory Bobby saved to enjoy just before his death in the aptly named "Death's Door." It wasn’t his boys being the heroic badasses they are. It was Sam and Dean being completely normal brothers as they bickered over movie night snacks. If that doesn’t make your heart explode with love, then dissolve from grief, nothing will.
1. Swan Song. Sudden deaths are a painful shock but prolonged, planned deaths can be torture. “Swan Song” is essentially an elongated view of Sam's demise, redemption, and an ode to power of love in one hour so gut-wrenchingly intense I’ve only watched the entire thing twice. Believe it or not,"Supernatural" struggled in the ratings at that time, and this episode was conceptualized as a series finale. The show has lived on for six more seasons, but this is still the scale in which “Supernatural” heartbreaks are measured.
It was a tragedy in itself how many other moments were left off this countdown. What are your favorites? Hit up the comments section below.
Give your feels a workout with "Supernatural" every Wednesday on The CW at 9/8c.
Small Screen Girl
I am an unabashed pop culture and TV-aholic with no plans to ever seek treatment. Explore this blog and see just how deep my obsession goes.