Supernatural could never end. Sure, the show ceases to exist without Jensen Ackles and Jared Padalecki, but as long as they’re still alive and kickin’ it, the show goes on. Hell, the two stars could be 85 years old, sauntering around with nurses, and you could still find a way to make it work. That’s the power of this series, and also a testament to its seemingly infinite sandbox — the best in the business, come to think of it.
None of this is hyperbole. For 15 years, the long-running CW series has run the gamut and back when it comes to world-building. We’ve seen Sam and Dean Winchester ascend to heaven, discover other worlds than these, join the Scooby gang, play themselves, attend Supernatural fan conventions, and flip through channels. At some point, the depths of hell become so commonplace, the two treat the place like a rest stop.
There have been rough patches, sure. Season 6 takes some time to find steadier footing after series creator Eric Kripke concluded his five-season run. And, yeah, Season 12 struggles to find conflict after, well, seeing God throw down. But, the writers always find another misadventure for the two Winchesters to solve, even if it’s something as obvious as staging an entire episode in their car. They make it work.
Even now, this team just can’t quit. During their recent interview with Variety, Ackles and Padalecki admitted that they have another idea for an episode — one they just couldn’t fit into Season 15. “We called it Naked Supernatural,” Ackles admitted. “It was like the Naked Gun version of Supernatural. Everything that happened in the episode would have been tongue-in-cheek.” Fans are already demanding it.
Odds are they’ll see it come to fruition. Again, there’s just no end in sight for the Winchesters, and that’s not because the creators are trying to exploit something and ruin a good thing. No, it’s because it’s too good a thing to walk away from — even after 15 years and 15 seasons. The fact that the creativity keeps coming speaks volumes about the series as a whole, and says even more about the characters in question.
They’re family, we’re family, and it’s been one long family road trip ever since the show premiered on Tuesday, September 13, 2005. Let that date sink in. Try to imagine all the things that have happened since then: the places you’ve seen, the people you’ve met, the culture we’ve experienced. That should help contextualize the road so far, and add some weight to the entire journey. Will it end in November? Who knows.
All we can do is carry on.
Co-Founder and Editor-in-Chief
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15. “The Curious Case of Dean Winchester”
Season 5, Episode 7
The Road So Far: Stalled on trying to halt the Apocalypse, the Winchesters do what they do best: save people and hunt things like malevolent presidents, powerful children, and old foes.
Now: The Winchesters roll into a town to probe the peculiar death by old age of a 25-year-old man. Bobby (Jim Beaver), Sam (Padalecki), and Dean (Ackles) then stumble upon a poker game where players can win big, but the stakes are even bigger. In this game, you bet years off your life, and both Bobby and Dean find themselves on the losing side of the game.
Carry On: Ah, there’s nothing better than a good ol’ poker flick. Maverick, Rounders, Casino Royale, The Gamber — with James Caan, of course — all boil down to one thing: the stakes. The sweatier the stakes, the better the game, and for Supernatural, writers Sera Gamble and Jenny Klein truly subverted the medium by tossing in a little Benjamin Button action. It’s one of the more brilliant conceptual marriages in the show’s history, toeing the line between comedy and intrigue as we watch Dean go grey.
None of it would work if it weren’t so tightly wound. Gamble and Klein tie all the threads efficiently, from the story-of-the-week backstory involving Patrick (Hal Ozsan) and Lia (Pascale Hutton) to Bobby’s ensuing arc involving his own physical ailments. It’s razor sharp genre writing that affords the entire cast to flip the board. The greatest swap is seeing an elder Dean huff and puff behind an in-control Sam, who channels his inner Caan as he gambles his own life for the house. It’s funny, it’s gripping, it’s a diamond one-off.
Team Free Will: Ackles reunites with his former Dawson’s Creek pal in Ozsan. Also, we get a good look at Dean as an old man via Medical Center veteran Chad Everett. How about that.
Season 14, Episode 20
The Road So Far: The young Nephilim Jack (Alexander Calvert) has gone too far, killing Mary in a blast of anger. Sam, Dean and Castiel have locked him up in the Ma’lak Box in an effort to contain him – but it doesn’t work and now he’s free.
Now: Sam and Dean are on the hunt for Jack, who is causing chaos around the world by forcing people to “stop lying.” Elsewhere, Chuck (Rob Benedict) appears with a weapon too good to be true, the Equalizer. In a classic Supernatural catch-22, the weapon promises to kill Jack, but also vanquish the individual that wields it. Naturally, the ensuing confrontation changes everything forever.
Carry On: The title “Moriah” comes from the Book of Genesis — specifically, chapter 22, verse two — and reads, “And He said: ‘Take now thy son, thine only son, whom thou lovest, even Isaac, and get thee into the land of Moriah; and offer him there for a burnt-offering upon one of the mountains which I will tell thee of.” So, it’s not particularly hard to parse out what showrunner Andrew Dabb was thinking when he chose this title for the season finale. After all, Jack has become like a surrogate son to Dean, and these last few episodes have been winding up to Dean being forced to kill Jack — an act he cannot bring himself to commit.
Beyond that drama, the revelation that Chuck, aka God, has been orchestrating all their misery for their entire lives is quite the game-changer for Supernatural. It turns God from an absentee father of a benevolent nature to one of a malevolent force that actually makes quite sense when you consider the long-game storytelling. Narratively, the twist breaks the fourth wall in a different way, dissecting the agency the characters have when they’re being written by someone. They don’t want the pain that’s being thrust upon them, and that’s the key to it all – it’s finding the will to fight against what’s already been written.
More importantly, if we drill down deeper, God’s love of putting the Winchester brothers through pain and suffering is a commentary on the audience who watch Supernatural. They, too, love it when the Winchesters experience loss and heartache. It’s a narcotic to the fans and the cheapest one on the market – the written word.
Team Free Will: Benedict reprises his role as Chuck/God here, while Lisa Berry returns as the formidable reaper, Billie.
13. “The Real Ghostbusters”
Season 5, Episode 9
The Road So Far: The Winchesters meet their biggest fan, a fan fiction scribe named Becky Rosen (Emily Perkins). They also discover that one of their oldest nemeses, the Trickster (Richard Speight Jr.), is actually the archangel Gabriel.
Now: Becky uses Chuck’s phone to trick the Winchesters into showing up at a convention for the Supernatural books. Unfortunately for the cosplaying con-goers, a real poltergeist shows up on scene and begins making violent trouble.
Carry On: “The Real Ghostbusters” is a love letter to fans, and one of a handful of meta episodes in the show’s catalogue. Taking place at the first-ever Supernatural convention, it’s a hilarious look at the series from the perspective of its viewers — but also through and Dean and Sam.
Naturally, the two brothers are understandably shocked to see people cosplaying them, talking in gruff voices, and even reenacting personal conversations between the two brothers. And while the episode pokes fun at fan culture with its nitpicking questions and analytical theories — “Frightened Little Boy – the Secret Life of Dean Winchester” and “The Homoerotic Subtext of Supernatural”, anyone? — writers Kripke and Nancy Weiner never shame the fans. Instead, they explore the uplifting power of fictional characters.
Two such characters Barnes (Ernie Grunwald) and Damien (Devin Ratray) steal the show as partners and con-goers inadvertently roped into helping Sam and Dean on the LARP Ghost Hunt that veers a little too close to reality. What’s more, their touching moment at the end of the episode is a nice step toward inclusiveness on a show working towards diversity. Meanwhile, Prophet Chuck gets a hero moment, and No. 1 fan Becky Rosen is fantastic, creepily ogling Sam before “dumping” him for Chuck. And lest we forget, it’s all set against the backdrop of a truly creepy ghost story. Who wouldn’t want that?
Team Free Will: This episode features post credits ad lib by Benedict as Chuck; the second appearance of Perkins as Becky, and the first mention of the demon Crowley (Mark Sheppard).
12. “The Monster at the End of This Book”
Season 4, Episode 18
The Road So Far: Sam and Dean are embroiled in an all-out war involving angels and demons, only to learn from a new angel on the block, Zachariah, that they cannot escape their fate.
Now: While Lilith makes her final moves, Sam and Dean stumble upon a series of novels that detail all the trials and tribulations in their life called Supernatural, all written by a man called Carver Edlund.
Carry On: By Season 4, the series was already waist-deep in meta humor, mostly thanks to the arts and crafts provided by the Trickster (Speight Jr.). Even so, “The Monster at the End of This Book” still felt like a total game changer by acknowledging the then-budding fan base without losing any steady ground. Writers Julie Siege and Nancy Weiner did their homework, too, managing to even squeeze in a reference to the online Slash fiction that has become a curious part of the show’s legacy.
More importantly, though, Siege and Wiener opened up another door for the series creatively. Looking back, there’s a lot of table-setting in this episode, and the idea that Supernatural was an in-world entity helped condition later concepts like alternate universes, animated crossovers, and even the inclusion of Oz. Not to mention, it also introduced arguably the most important character of the series beyond Sam and Dean: Carver Edlund (Benedict), aka Chuck, aka God.
It’s through Chuck that Supernatural became what it is today, and his introduction is seamless. Christ, Benedict plays the role with so much burden and conviction that you really do believe he’s this exhausted Prophet of God — even when he literally says: “Obviously I’m a God… I write things and then they come to life. Yeah, no, I’m definitely a God. A cruel, cruel, capricious god.” Granted, fans sniffed out his true identity long before Season 11’s “Don’t Call Me Shurley”, but hey, hindsight’s 20/20.
Team Free Will: Well, as mentioned, Benedict joins the mythos. Keep up!
11. “LARP and the Real Girl”
Season 8, Episode 11
The Road So Far: Dean, his vampire friend Benny (Ty Olsson), and Castiel (Misha Collins) have escaped Purgatory and the prophet Kevin is working to decipher a “demon tablet” in the hopes to banish all demons to Hell for good.
Now: A mysterious case involving a man being drawn and quartered drags the brothers into the world of Live Action Role Playing and back into the company of the fiery, friendly computer hacker, Charlie Bradbury (Felicia Day).
Carry On: “LARP and the Real Girl” sees the return of fan favorite Charlie Bradbury, aka the Queen of Moons, lead a group of LARPers (or Interactive Literaturists) living out their medieval fantasies in attempt to escape the mundanity of their lives. While Sam is mostly dismissive of the concept, Dean is into it, offering Charlie tips on the battlefield and enjoying his new role as Handmaiden. True to form, Charlie is a non-traditional queen, wearing battle clothes, sparring with squires on the pitch, and even rescuing the damsel in distress. Eventually, she saves the day by destroying the book of spells and freeing the fairy that caused all the mayhem, even making out with said fairy before she returns to her magical realm.
But there’s a flip side to this coin: While all the participants take their roles seriously, writer Robbie Thompson presents a darker side of this world through the episode’s villain Gerry (Hank Harris), Boltar the Furious. Unlike Charlie and her friends, Gerry is someone who takes the game so seriously he is willing to murder his friends for an imaginary role. It’s an important commentary on escapism taken too far and the ensuing toxic fandom that tends to poison any fan culture. But there’s a tangential lesson to also be learned when Sam and Dean are mistaken for FBI LARPers: Like Charlie’s crew, they chose to be hunters, a life that gives them more purpose and fulfillment than the “normal” lives they’ve both tried to lead.
On a side note: Special shoutout to the Braveheart reenactment concluding the episode. It may be the only speech Dean knows, but it’s the perfect ending to a fun and empowering episode.
Team Free Will: This episode is the second appearance of Charlie after she was last seen in the Season 7 finale, The Girl with the Dungeons and Dragons Tattoo.
Season 3, Episode 13
The Road So Far: Dean has sold his soul to a crossroads demon who gave him one year before his time would be up. The demon that plans to collect on Dean’s soul, Lilith, has made her presence known in a violent, explosive way.
Now: Sam and Dean find themselves trapped alongside the twerpy, ghost hunting duo of Ed Zeddmore (Travis Wester) and Harry Spengler (A.J Buckley) and their gaggle of goons as they seek to investigate and stop a vicious poltergeist in the most haunted place in America, The Morton House, the events of which are told via the “unsolicited” reality television pilot, Ghostfacers.
Carry On: In the Season 3 book companion for Supernatural, the writers talk a lot about how the 2007-08 WGA strike affected how they chose to plot episodes out. In the case of “Ghostfacers”, it involved putting the Winchesters in a position where they wind up as second bananas on their own show. Not surprisingly, given writer Ben Edlund’s involvement, the episode is rife with wisecracks, be it the constant bleeps on account of the brothers’ constant profanity or the ‘Facers calling the Winchesters hicks when the boys show up to the scene blaring Grand Funk Railroad’s “We’re an American Band”. What’s more, Wester and Buckley have crackerjack chemistry and work so well as competent doofuses.
Despite the litany of chuckles on display, the episode delivers on its promise of spooky fare. The concept of death echoes is introduced, which finds specters fated to relive their death over and over again. So, that’s terrifying. Also eerie is the main villain, Freeman Daggett, who steals bodies from the morgue he worked at when he was alive and uses them to create his own little sick soiree. This leads to a disturbing scene where Daggett murders novice Ghostfacer Corbett (Dustin Milligan), all while Sam looks on in horror – the skipping record playing Lesley Gore’s “It’s My Party” is the cherry on top of the creep cake. This arc even manages to find room for a sweet little moment between Ed and Corbett, who shows romantic affection for him.
All in all, it’s a very versatile hour of television.
Team Free Will: Buckley and Wester make their first appearance since Season 1’s “Hell House”. Milligan would go on to be the kindhearted vet, Ted, on the popular Canadian program Schitt’s Creek.
09. “The French Mistake”
Season 6, Episode 15
The Road So Far: Sam and Dean are out fighting a new breed of monsters called Alphas. Meanwhile, a civil war has broken out in Heaven, led by the archangel Raphael (Demore Barnes).
Now: In an effort to keep the brothers safe from angel hitman Virgil (Carlos Sanz), their ally Balthazar (Sebastian Roché) zaps the Winchesters into an alternate universe, where Sam and Dean are respectively known as Jared Padalecki and Jensen Ackles and are starring on a television series called Supernatural.
Carry On: “The French Mistake”, named so for the meta ending of Mel Brooks’ Blazing Saddles, is hardly the first or last time that Supernatural would break the fourth wall. This time around, though, the series’ reliable scribe Ben Edlund fired a double-barrel shotgun blast of salt straight at the barrier between the characters and their audience.
This break allowed both Padalecki and Ackles to erase any semblance of “vanity” by picking apart their on- and off-screen personas. Together, they poked fun at Jensen’s early career soap opera roles, Padalecki’s romantic life, their supposed dislike for each other, the implied creative bankruptcy of the crew (Season 6 is used as a constant, exasperated refrain), and the show’s rabid, oft-toxic fanbase.
Though the episode is wrapped up tightly in Season 6’s overarching grim mythology, there’s some hilarious bits here — you know, like the riotous montage of “Sam” and “Dean” acting terribly. It’s also nice to see the normally dour, restrained Misha Collins being allowed to stretch his wings, pun intended, as a dopey tweeting twerp. It’s even funnier when you realize that all the tweets he sent out in the episode, he actually tweeted when the episode originally aired.
It doesn’t get more meta than that.
Team Free Will: Genevieve Padalecki returns to the series, but this time playing herself. Brian Doyle-Murray guests playing the show’s longtime director/producer Robert Singer.
08. “Death’s Door”
Season 7, Episode 10
The Road So Far: Dean, Sam, and Bobby discover that the Leviathans and their charismatic leader Dick Roman (James Patrick Stuart) are peppering Turducken sandwiches with a food additive to fatten up humans so they’ll be ripe for consumption. During a violent raid on one of the warehouses, Dick gets a lucky gunshot straight to Bobby’s dome and the Winchesters are reasonably horrified at what may come next.
Now: Sam and Dean struggle to come to terms with Bobby’s possible death and in his “mind palace,” Bobby travels through his various memories in life while outrunning the Reaper with the help of his pal Rufus in order to deliver a final, important message to the boys.
Carry On: Ever since his debut in the first season finale, “Devil’s Trap”, Bobby Singer has been a crucial part of Supernatural. Buried beneath his gruff, blue-collar shell was a single important element that kept the brothers grounded throughout their worst moments – his paternal instinct. He knew when to knock them upside their head when they were about to make another classic suicidal Winchester move, and that is key to keep your story’s world, characters, and mythology from going topsy-turvy.
“Death’s Door”, written by longtime Supernatural stalwart Sera Gamble, glides through its 40+ minutes, zipping back and forth through the fragmented moments in Bobby’s past and present. At times, it almost feels like a staged play with Bobby’s house being used to shift to different time periods. However, the important piece of the episode is Bobby’s final subconscious memory: Sam and Dean bickering with each other. It’s imperfect, but that’s why it works. It’s sentimental without becoming schmaltzy.
Of course, this isn’t the last time we’d see Bobby: He’d choose to stick around as a spirit to help the boys out here and there, much to their detriment as we’d come to learn. What’s more, he would return as “alternate Bobby” in the latter era seasons of the show, giving fans a chance to hang around with the guy again. Still, given how integral the OG character is to the show’s core, “Death’s Door” is one tremendous curtain call that certainly didn’t leave a dry eye in the house.
Team Free Will: Steven Williams reprises his role as Rufus Turner.
Season 13, Episode 16
The Road So Far: Sam and Dean’s mother Mary (Samantha Smith) and their “adopted son” Jack (Calvert) are trapped in a post-apocalyptic world where an alternate version of archangel Michael (Christian Keyes) rules over a devastated and destroyed Earth. The boys are running around gathering ingredients to open a rift and bring them back home.
Now: Sam, Dean, and Castiel find themselves trapped in television (again) on account of a ghostly boy and the cursed object that its soul is attached to, but this time, they’re stuck in an episode of Scooby Doo, namely a reconfiguration of “A Night Of Fright Is No Delight” from 1969’s “Scooby Doo, Where Are You!”
Carry On: For Supernatural’s first television crossover, director Robert Singer and his crew only ensured the best. The animation style is solidly done throughout, keeping the Winchesters’ and Cass’ sharp, good looks but making them just cartoony enough to fit into the Hanna-Barbera illustration model set forth decades ago. Ackles relishes diving into the childlike glee of Dean Winchester and his outright love of the original hip monster hunting gang. His character even gets a little pathos when he admits that all the times that Dad abandoned him and Sam, his one constant was always having Scooby Doo to watch.
There are solid bits throughout the episode: Dean’s constant irrational hatred of Fred and his piggish behavior in thirsting after Daphne; Cass’ bemusement at the predicament that he finds himself in; and Sam’s romantic dalliance with Velma. Though the episode is packed with its fair share of humor, it still manages to capture the dramatic weight of some of Supernatural’s best episodes. After all, there’s something deeply profound about the Scooby Gang coming face to face with their own mortality and learning that there are more important things in the world than unmasking crooked real estate developers.
Of course, in keeping with the writers’ way of cohering the two plots, the real-world baddie who’s been siccing the ghost kid onto innocent folks here happens to be a … real estate developer.
Team Free Will: Matthew Lillard, Kate Miccuci, Frank Welker, and Grey Delisle-Griffin all reprise their voice acting roles as Shaggy, Velma, Fred/Scooby and Daphne from the various Scooby Doo series.
Season 2, Episode 12
The Road So Far: Earlier, in Missouri, a murderous shapeshifter has taken on Dean’s likeness, causing him to have to fake his death to escape incarceration.
Now: The Winchesters are in Wisconsin investigating the newest crime in a series of robberies. When they go undercover at a bank to discover the origin of the monster responsible for the deeds, a paranoid, gun-toting security guard busts in to try and stop the menace himself. Soon after, the FBI and police show up.
Carry On: Things were getting a little too easy for Sam and Dean. After all, there are only so many classic rock icons they could mine before someone caught on. That someone turned out to be FBI Special Agent Victor Henriksen (Charles Malik Whitfield), who, as we learn in this Season 2 stunner, has been hot on their tail since the events of Season 1’s “Skin”. This revelation not only adds to the mounting tension of “Nightshifter”, but also shatters the glass bubble that had been protecting the Winchesters up to that point.
By making Sam and Dean public enemies and outlaws, writer Ben Edlund stenciled in a distinctive wrinkle to the show’s universe, proving that the spooky wasn’t relegated strictly to the backroads. By that same measure, Edlund also revealed there’s no room for novices in this business through the tragic fate of Ronald Reznick (Chris Gauthier). No, this is a downright dirty job, one that brings blood, sweat, and tears, a lesson that Reznick learns when he’s shot in the middle of the bank trying to fight the good fight himself.
Threads aside, “Nightshifter” is one of the earliest examples of how Supernatural can deliver a bottle episode that also naturally aides the mythology. It’s a delicate dance that hearkens back to the glory days of The X-Files, a series this show (and certainly this episodes) is indebted to both narratively and stylistically. The fact that this chapter ends with so much swagger — no doubt elevated by the series’ greatest needle drop — is a testament to the confidence of the show’s creators. They knew what they had.
So did the fans.
Team Free Will: Whitfield arrives as one of their greatest foils.
05. “Changing Channels”
Season 5, Episode 8
The Road So Far: The brothers contend with the weight of the Apocalypse and the sobering reality that, in the future, Sam will eventually say yes to the Devil and bring nightmarish horrors to the world.
Now: Sam and Dean find themselves stuck inside the boob tube, flying through different types of series: medical dramas, police procedurals, and Japanese game shows, all at the whim of their old enemy, The Trickster.
Carry On: One of the most creative episodes in Supernatural’s run, we open on a brightly lit hotel room complete with a laugh track and a comically large sandwich waiting for Dean. We’re not sure what’s going on, but one thing’s for sure: Dean’s gonna need a bigger mouth. Next, we’re treated to a perfectly ’90s sitcom theme song, complete with ghosts in the closet, football in the park, and bicycles made for two.
After a brief setup, we launch into a string of television parodies starring Sam and Dean, from Knight Rider, to a herpes commercial, to a hilarious homage, to the sunglasses-heavy one-liners of CSI: Miami. (The less said about that game show, the better.) The most successful segment involves the boys playing doctors on Dean’s “guilty pleasure” show, Dr. Sexy M.D. It’s a clear reference to Grey’s Anatomy with its sensitive acoustic soundtrack, “seriously”s, and a big wink at former cast member Jeffrey Dean Morgan and his recent “doctor dating a ghost” storyline.
The concept is bizarre, but what do you expect when you’re dealing with the Trickster? It’s a fearless episode that succeeds largely because of the comedic chops of its two leads. We dare you to love Dean more than when he’s ogling Dr. Sexy like a starstruck fanboy. Handled differently, this could have easily become a Jump the Shark moment for the show. And yet, against all odds, it not only works, but remains one of the most memorable and GIF-able episodes in Supernatural history.
It’s proof that swinging for the creative fences sometimes can lead to a grand slam.
Team Free Will: This is the third appearance of Richard Speight Jr. as The Trickster and serves as an important turning point in his character’s development.
Season 11, Episode 4
The Road So Far: The Darkness, a powerful, ancient entity is free. Sam and Dean stand their ground and work to understand the mysterious new villain they’re faced with.
Now: Sam and Dean journey to Oregon to solve a murder. Along the way, the brothers share their innermost feelings, reminisce about the past, and slay beasties, the events of which are all told from the perspective of the most essential member of Team Free Will – the Impala.
Carry On: Eleven seasons into any show, the imagination in the writers’ room begins to accept whatever hurdles it can dream up. On paper, “Baby” reads like one such test: “Could we actually shoot an entire episode from the confines of the Impala?” The answer turned out to be a resounding yes. But, as with most creative leaps in the show’s long-enduring sandbox, writer Robbie Thompson managed to take a brazen idea and turn it into an opportunity to create new memories with old pasttimes.
Like “Weekend at Bobbie’s” before it, “Baby” sheds a light on a facet of the show’s narrative that is all too often overlooked and taken for granted. With “Bobbie’s”, we were given a close look at Bobby’s hustle and bustle behind the scenes, but with “Baby”, we see how essential the muscle car is for the Winchesters. It’s not just their home away from home, it is their home. It’s where we first met the two brothers, and it’s likely where we’ll see them in the final moments of the show come November.
Then again, none of this would work without its razor-sharp execution. Like all the greatest bottle episodes, Thompson shakes out the best ideas from the crackerjack concept, wiring the entire episode with a litany of visual and situational gags that bring out the best in Ackles and Padalecki. Meanwhile, veteran Supernatural director Thomas J. Wright keeps things breezy, avoiding what could have been a very claustrophobic episode given the circumstances. Never once do you feel the need to roll down the window.
Well, at least not until Seger starts playing.
Team Free Will: If that deputy looks familiar, there’s a reason. That’s Teach Grant, who played adult Henry Bowers in It: Chapter Two and has also starred in just about every show to ever hit the boob tube.
03. “Fan Fiction”
Season 10, Episode 5
The Road So Far: After his death in Season 9, Dean has finally shaken loose of the demonic veil of the Mark of Cain with the help of Sam, Castiel, and Crowley.
Now: Sam and Dean head out to an all-girls school to investigate the disappearance of a teacher. Upon their arrival, they discover that the school is putting on a very special play about two very special characters – themselves.
Carry On: Supernatural’s 200th episode is a charming love letter to fans, especially the female ones, and an invitation to view the show through diverse lenses. It’s a meta episode (cue character eye roll), not too dissimilar from Season 5’s “The Real Ghostbusters” (see above), that’s both introspective and accepting of outside interpretations.
For a show with a rabid fanbase and extraneous theories, “Fan Fiction” makes peace with the fact that once art is out in the world, it’s open for interpretation. MVP scribe Robbie Thompson — this marks his third appearance on this list, if you’re keeping count — suggests that the highest compliment is to love a story so much that you want to be part of it as well.
That idea culminates in the last act of the staged on-screen production. Writer-director-actor Marie (Katie Sarife) plays Sam as she defeats the manifested monster that would steal her creative spirit, all while the real Sam simultaneously destroys Calliope (Hannah Levien) behind the scenes. Set to “A Single Man Tear”, which alludes to the emotional moments between the brothers, it’s a powerful moment that gives voice to fans who would find empowerment in the themes if not the identities of the characters.
The real cherry on top of the pie — oh, does Dean love his pie — is a closing choral cover of Kansas’ “Carry On My Wayward Son”. The tearful rendition of the show’s de facto theme is a touching and moving tribute to what as then a staggering 200 episodes.
Team Free Will: With a surprise cameo at the end, this episode marks the first appearance of Chuck Shurley (Rob Benedict) since Season 5. His “not bad” is a poignant ending to a fantastic episode.
02. “Dark Side of the Moon”
Season 5, Episode 16
The Road So Far: The chaos of the Apocalypse is in full swing. Allies are dying, Horsemen are claiming victims, and a beast slouches towards Bethlehem, hoping to get a “yes” from Sam Winchester.
Now: Sam and Dean have been shot and killed by hunters furious that Sam jumpstarted the Apocalypse. They wake in Heaven, and while trying to stay hidden from the villainous Zachariah, travel through memories of the past while seeking out an angel who speaks with God.
Carry On: Heaven could have gone so wrong for Supernatural. In lesser hands, the entire ascension would have likely been too sappy, too saccharine, or too syrupy. But as we all know, writers Andrew Dabb and Daniel Loflin are hardly slouches behind the typewriter. So, it’s perhaps not too surprising that they penned the most emotional hour in the franchise’s history, delivering a parable on brotherhood and family that brings a tear to this writer’s eye even as he types these very words.
Narratively, “Dark Side of the Moon” really digs into not only what binds the two brothers together, but what also sets them apart. As we learn through their journey in the proverbial clouds, the two brothers have differing definitions of happiness. What starts out as a beautiful memory under fireworks between Dean and Sam eventually unfolds into lonely motel rooms with Sam and his pup. It’s a sobering dichotomy for both brothers, and one that winds up paying dividends to their relationship — and ours to them.
None of this would work if it weren’t so goddamn beautiful. Director Jeff Woolnough earns major kudos behind the camera, turning every section of this surreal excursion into a must-have portrait — from the Fourth of July opening to the escape into The Garden with Joshua (Kerry van der Griend). The way he connects all these memories with winding, moonlit roads only adds to the episode’s dreamy yet grounded aesthetic. Because of this, to crib from Belinda Carlisle, Heaven wound up feeling like a place on Earth.
If only Dean would approve that song.
Team Free Will: The great Kurt Fuller returns as Zachariah, as does Samantha Smith as Mary Winchester. The District star Roger Aaron Brown offers a welcome turn as Joshua.