Supernatural is the CW’s longest-running sci-fi / fantasy series, accumulating over 300 episodes during its 15-year run. Throughout its fifteen seasons, the show was not exactly known for its comedy, more often than not, bringing the audience to tears with some truly gut-wrenching scenes.
Over the show’s run, multiple episodes from each season had fans a complete mess by the end. From season one’s car crash cliffhanger to multiple beloved character deaths like Bobby (Jim Beaverand Charlie (Felicia Day), Supernatural was a show that proved over and over again just how much they liked to torture us fans.
“Devil’s Trap” (Season 1, Episode 22)
It was unknown whether Supernatural would return for season two until two weeks after the finale aired. The episode was full of emotional moments but being unsure whether we’d get closure on everything only made things more upsetting.
Season one ended on a major cliffhanger, with Sam, Dean, and John (Jared Padalecki, Jensen Ackles, Jeffrey Dean Morgan) left bloody and unconscious following a demon-possessed truck driver colliding with the Impala. With Dean already severely injured and John shot, their fate remained unknown for five months.
“All Hell Breaks Loose” (Season 2, Episode 21 and 22)
If there’s one thing that every SPN fan knows, nobody stays dead for very long. But that was unknown in 2007, making one of the main characters’ deaths even harder to process.
The first episode in the two-part season finale ended with Dean and Bobby finding Sam just in time to see him get stabbed. Sam heartbreakingly died in Dean’s arms, but perhaps the saddest moment came in the second part with Dean’s speech to Sammy after he’d died. Between Jensen’s phenomenal acting and the thought of losing Sam, this will always be an emotional watch.
“No Rest For The Wicked” (Season 3, Episode 16)
The shortest season of Supernatural brought with it one of the most graphically heartbreaking season finales. After selling his soul the previous year to save Sam, Dean’s time is up, and the hellhounds have come to collect.
After Lillith possesses Ruby (Katie Cassidy), she sets the hellhounds on Dean, tearing him apart. Between his pained screams and Sam’s cries for it to stop, we could not help but cry along with him. Making it worse, the episode ended with Dean screaming for Sam in hell, hooks in his shoulders and covered in blood.
“When The Levee Breaks” (Season 4, Episode 21)
Season four was a bumpy ride for the boys. Whether you were left distraught by Dean’s confession about his time in hell or emotionally unstable after that Dean and Castiel (Misha Collins) hospital scene, the writers did not hold back on the gutwrenching moments.
Their relationship was tested multiple times, with Sam choosing Ruby (Genevieve Padalecki) over Dean on more than one occasion. But seeing the brothers fight so brutally was gut-wrenching. From Sam strangling Dean and Dean telling Sam to never come back, this is still extremely sad even over a decade later.
“Swan Song” (Season 5, Episode 22)
With the fantastic storylines, the introduction of Rob Benedict as Chuck, and the further exploration of Lucifer (Mark Pellegrino) following the nail-biting season four finale, it’s clear to see why this season remains so many people’s favorites.
Season five shattered hearts effortlessly with episodes like “Abandon All Hope,” which brought the deaths of Ellen and Jo. Only intensifying the pain as the season culminated in a Lucifer-possessed Sam beating Dean to a pulp, killing Castiel and Bobby, and seeing a heartbroken Dean defeated on the ground. And if that was not sad enough, a montage of the brothers undoubtedly destroyed any emotional stability that remained.
“The Man Who Knew Too Much” (Season 6, Episode 22)
Following the popularity of season five, season six wasn’t everybody’s favorite, but it had some great episodes throughout, including “Weekend at Bobby’s” and “The French Mistake.” The most heartbreaking episode came with the finale after Castiel tore down the wall inside Sam’s head.
What followed was Sam’s internal battle as he remembered everything he’d done since hell, including the time he’d spent without his soul. Seeing Sam’s struggle and the route the writers took after making Cas the series antagonist resulted in some heightened emotion for sure.
“Death’s Door” (Season 7, Episode 10)
“Family don’t end with blood, boy!” This season three quote remains in the heads of every Supernatural fan even following the show’s end back in 2020. The deliverer of this well-known quote was none other than Bobby Singer, the much-loved father figure to Sam and Dean.
“Deaths Door” was a Bobby-centric episode and, throughout its entirety, left fans uncertain whether he would survive following a gunshot wound to the head. Bobby woke up, smiled, and sadly died with his boys by his side, but not before delivering one of his most iconic quotes. “Idjits.” Excuse us while we cry all over again.
“Sacrifice” (Season 8, Episode 23)
There seems to be a running theme going, with the saddest episode of Supernatural being the finale of most seasons, and season 8’s was no exception. With an episode entitled “Sacrifice,” it was bound to be an emotional ride.
Between Sam confessing that his greatest sin was how many times he’d let Dean down and Dean’s, “do not you ever think that there is anything, past or present, that I would put in front of you,” we were in bits , only intensified with one of the most heartbreaking Winchester brother hugs of the show.
“Do You Believe In Miracles?” (Season 9, Episode 23)
The mid-point of season nine saw the beginning of a new struggle for Dean when he took on the Mark of Cain. In a bid to defeat Abaddon, Dean took on the burden of the mark, but it did not end well for the eldest Winchester.
In the season nine finale, Dean was stabbed through the chest by Metatron (Curtis Armstrong). While leaning heavily on Sam, he stops and tells him, “I’m proud of us,” before dying in his brother’s arms. Between Sam’s pleas for him to wake up to that shocking black eye reveal at the end, this episode was chock-full of emotion.
“Brother’s Keeper” (Season 10, Episodes 23)
From 9×11 to 10×23, Dean continued further and further down the dark path inflicted by Cain’s mark. From becoming a demon and threatening to kill Sam to beating and nearly killing Cas with an angel blade, the Mark of Cain took a heavy toll on him, only made worse by Charlie’s murder.
We knew this would be an emotional ride when Dean said, “Sammy, close your eyes.” But when Sam showed him pictures of him with his mom to help him find his way back, it tipped us over the emotional ledge. From the tears in Sam’s eyes to the pain on their faces, this wasn’t one to watch without a trusty box of tissues.
“Red Meat” (Season 11, Episode 17)
While it may be season 11’s most underrated episode, it was still a hard one to watch without shedding a tear or two. Between Sam being shot in front of Dean and Dean making the hard decision to leave his brother behind, this episode was full of emotional scenes that just kept coming.
Not knowing Sam is alive, Dean decides to kill himself in an attempt to make a deal to bring Sam back. Any episode where the brothers are trying to save each other instantly tugs on our heartstrings, and between Sam’s pain and Dean’s grief, this one was no exception.
“All Along The Watchtower” (Season 12, Episode 23)
No. This one still hurts to think about even five years on. Not only did we lose Rowena (Ruth Connell), but Crowley (Mark Sheppard) and Castiel as well. While Cas would return early in season thirteen, Crowley would not, and at the time, it was unknown if anybody would.
While season twelve did not lack emotional episodes, none hit as hard as this. Losing not one, not two, but three beloved characters at once in the season twelve finale was a crushing blow, and it came as one hell of a shock. From Rowena’s charred remains, Crowley’s sacrifice for the boys, and the false hope after Cas made it back through the rift, the painstaking five-month wait for the next season felt more like fifty years.
“Lost And Found” (Season 13, Episode 1)
Following the traumatic events of the season twelve finale, the thirteenth season opener was just as soul-crushing. After Castiel, Crowley, and Kelly’s deaths, the boys were reeling from the loss as they tracked down Lucifer’s son, Jack (Alexander Calvert).
Fans may have quickly fallen in love with the Nephilim, but it did not prepare anyone for what the ending was about to throw at us. Between saying goodbye to Castiel, Crowley, Kelly, and Mary, who they believe Lucifer has killed and giving Cas a hunter’s funeral, there wasn’t a dry eye at the end.
“Lebanon” (Season 14, Episode 13)
In Supernatural‘s 300th episode, we knew they would do something big, and we knew it was bound to break us in classic SPN fashion. We weren’t wrong. However, we did not know how much it would hurt.
Jeffrey Dean Morganmade his long-awaited return in this highly anticipated episode, as it had been 12 years since his last appearance. Between John and Mary’s reunion and the Winchester family dinner to having to say goodbye once again, this episode was pure heartache all the way through. Someone grab the tissues.
“Despair,” “Inherit The Earth,” and “Carry On” (Season 15, Episodes 18, 19, 20)
Come on! You can not just pick one of these now, can you? Whether you liked how the show ended or not, you can not help but confess to a waterfall of tears coming as a result of saying goodbye to Supernatural after fifteen years.
“Despair” bid farewell to a character loved by millions. Castiel admitted he loved Dean and sacrificed himself to save him. “Inherit The Earth” saw Chuck defeated after beating the boys to near death and Jack as the new and improved almighty. And “Carry on” was just pure soul-crushing material. From Dean’s speech and farewell to our beloved Bobby’s return and the brother’s reunion in heaven in their “Pilot” outfits, fans were a mess for days to come. Carry on, Supernatural family.
NEXT: Best Monster-of-the-Week Episodes From Each Season of ‘Supernatural’