40. ''The Song Remains the Same''
Season 5, episode 13
When the angels travel back in time to kill John and Mary before Sam is born, the Winchesters tag along to stop them. The battle kills Sam—who’s quickly brought back to life—and introduces us to Michael, who first appears in the body of a young John Winchester to put a stop to the madness. —Samantha Highfill
39. ''First Born''
Season 9, episode 11
With Dean and Crowley off to find the First Blade, thereby running into the ridiculously charming Cain, Sam and Cas team up to extract the rest of Gadreel’s grace from Sam. Along the way, Cas gives Sam a shockingly insightful PB&J-related speech that brings the two of them closer than ever before. As for Dean? Well, he walks away with the Mark of Cain on his arm. But what does it mean? —Samantha Highfill
38. ''Sympathy for the Devil''
Season 5, episode 1
Now that Lucifer has been freed, Sam and Dean are in a bit of a rut. Cas has apparently been killed, Chuck can only tell them so much or incur the wrath of his angel overlords, and Dean has been asked to serve as the archangel Michael’s vessel. Thankfully Cas returns and Dean denies Zachariah’s request, but there’s still one pesky little problem to deal with—Lucifer is around, and he’s found a host in Mark Pellegrino. —Jonathon Dornbush
37. ''The Magnificent Seven''
Season 3, episode 1
”Seven” introduces a number of interesting elements to the show, including another Biblically inclined villain in the Seven Deadly Sins. They are a thrilling foe to tackle as the show begins its third season, but the episode is also monumental for the first inclusion of a blade that can kill demons and the person who wields it. Ruby makes an impressive debut before going on to become a major player (in several different meat suits) over the course of the show. —Jonathon Dornbush
36. ''Holy Terror''
Season 9, episode 9
Rest in peace, Kevin. Everyone’s favorite prophet Kevin dies at the hands of Gadreel who, until this episode, had been posing as Ezekiel inside Sam’s body. The angel commits the murder as a sign of loyalty to Metatron who has set out on his quest for domination of Heaven. Castiel is hoping to thwart Metatron’s plans, but with the heartbreaking death of Kevin, the forces of good are beginning to dwindle. —Jonathon Dornbush
35. "Just My Imagination"
Season 11, episode 8
Leave it to Richard Speight Jr., who played the notorious Trickster God/Gabriel, to direct this delightfully impish episode. In “Just My Imagination,” Sully, Sam’s imaginary friend from his childhood, pops up to ask the Winchester boys for their help because someone is out there killing imaginary friends. The delightfully imaginative premise allows for the show to reconnect with emotional elements from the show’s early years that we haven’t thought about since, which was a nice treat. – Chancellor Agard
34. ''The Man Who Would Be King''
Season 6, episode 20
Told entirely from Castiel’s perspective, ”King” takes an intriguing alternative approach to the show’s traditional storytelling. Cas is revealed to have been behind many of the season’s most important events in a tragic but fascinating episode. —Jonathon Dornbush
33. ''When the Levee Breaks''
Season 4, episode 21
Sam spends most of the hour in demon-blood detox in Bobby’s basement before finally escaping to find Ruby. However, when Dean catches up with him, he finally says the three words that will cripple Sam: ”You’re a monster.” From there, the brothers have one of their biggest brawls to date, which ends with Sam leaving Dean bloodied on the floor of a hotel room. —Samantha Highfill
32. ''Pac-Man Fever''
Season 8, episode 20
Dean’s newest foe—videogame logic. Trapped in a Djinn-created dream, Charlie and Dean fight off wave after wave of super-soldier vampires. But the episode’s about much more than a crazy concept. It’s about learning to let go, which for Charlie means coming to terms with her comatose mother’s death. It’s a powerful lesson made all the more resonant by Felicia Day’s performance—and it’s okay to shed a few tears as she reads The Hobbit to her mother for what’s presumably the last time. —Jonathon Dornbush
31. ''99 Problems''
Season 5, episode 17
With the apocalypse starting to set in, Dean and Sam find themselves outnumbered by demons in a small town. Luckily, they find refuge in a nearby church where townspeople have gathered believing that one of their own is a prophet who can hear angels. Only what drunk Cas helps the guys discover is that she’s less of a prophet and more of a Whore of Babylon. After the guys take her down, Dean heads to Lisa’s to say goodbye having made up his mind to say yes to Michael. —Samantha Highfill
30. ''In My Time of Dying''
Season 2, episode 1
In the wake of the season 1 finale, the Winchesters are in bad shape. Surviving a car wreck, Sam and John contend with a few injuries while Dean lies dying in a coma. Winchesters do all they can to save each other, though, and John would never want to lose his sons to the line of work he introduced them to. So John sells his soul to Yellow Eyes, as well as the one thing that could kill the demon, the mystical Colt gun. —Jonathon Dornbush
29. ''Devil's Trap''
Season 1, episode 22
In an effort to save their father from Meg, the brothers enlist the help of Bobby Singer, a.k.a. the man who will become their surrogate father and a staple on the show. In terms of the mission, everything comes to a head when Yellow Eyes possesses John and Sam can’t find it within himself to shoot his father. If that’s not enough, the season ends on a massive cliffhanger when a car accident severely injures all three Winchesters. —Samantha Highfill
28. "Don't Call Me Shurley"
Season 11, episode 20
After 10 seasons, Supernatural finally introduced the big man upstairs: God, a.k.a Chuck (Rob Benedict), the author/prophet we met in “The Monster at the End of This Book.” Chuck summons Metatron to an undisclosed bar where he reveals his identity and asks the scribe’s help in writing his autobiography. However, their very meta discussion leads to a twist that’s even more surprising than the God reveal: the contemptuous Metatron ends up defending humanity and taking God to task for his absence, which is enough to convince God to join the fight to take down his sister. – Chancellor Agard
Season 14, episode 13
The series’ 300th episode brings Jeffrey Dean Morgan’s John Winchester back for one of the most emotionally charged episodes ever as Sam and Dean get to have some long-awaited conversations with their dad, and more importantly, all four members of the Winchester family get to enjoy a dinner together. John doesn’t get to stay for long, but his brief visit certainly has an impact. —Samantha Highfill
26. ''Fan Fiction''
Season 10, episode 5
In what writers and cast members have called a ”tribute” to the fans, the 200th episode of the series finds Sam and Dean at an all-girls school. The twist? The girls are in the middle of producing a play that’s inspired by Carver Edlund’s Supernatural books. So Sam and Dean are essentially watching a high school production of their life. Toss in Calliope, the goddess of epic poetry, and a number of unforgettable original songs—”A Single Man Tear” might be the best—and it’s a hilarious and heartfelt hour that any diehard fan would be proud of.—Samantha Highfill
25. ''Free to Be You and Me''
Season 5, episode 3
When Sam decides he no longer trusts himself to hunt alongside Dean, he gets a job as a bartender, which leaves Dean alone to help Castiel on his search for Raphael. Episode highlights include Castiel failing asleep with a prostitute and Lucifer visiting Sam for the first time. —Samantha Highfill
24. ''Hammer of the Gods''
Season 5, episode 19
After a storm washes out the road, Sam and Dean find themselves trapped in a hotel full of gods (Kali, Odin, and Ganesh, to name a few), who are meeting to discuss what to do about the upcoming apocalypse. To top it off, the episode ends with a showdown between Gabriel and Lucifer that unfortunately leads to Gabriel’s demise. Or is he still in that old porno video? —Samantha Highfill
23. ''Good God, Y'all''
Season 5, episode 2
The Four Horsemen were a consistently strong aspect of the show, and War’s appearance was no exception. Titus Welliver does an incredible job as War, setting the stage early in season 5 for just how imposing these figures could be. But really, his biggest impact is driving a wedge between Sam and Dean at a time when sticking together is key. And it never hurts to include an appearance by Ellen and Jo. —Jonathon Dornbush
22. ''All Hell Breaks Loose: Part 2''
Season 2, episode 22
The show’s first true villain, Yellow Eyes, meets his demise in a season finale that also foreshadows darker events on the horizon. Resurrecting Sam forces Dean to pay the ultimate price—his own soul, and not even the death of Yellow Eyes can erase that decision. It’s a powerful and early example of the show willing to push the brothers to the brink without ever giving them a break. The day is saved—even though an awesome railroad devil’s trap is destroyed—but trouble is only beginning to brew for Sam and Dean. —Jonathon Dornbush
Season 2, episode 12
Bank robberies have been around since movies and TV shows started being made, but few of these hostage scenarios are perpetrated by a shapeshifter. It’s one of the show’s most smartly tense scenarios, as the shapeshifter could be anyone in the bank, but it’s also an important episode for putting Sam and Dean’s work in context as we discover the FBI has been tailing them. Oh, and that escape scene set to ”Renegade” by Styx? Sam and Dean have never been quite as badass as in this episode’s final moments. —Jonathon Dornbush
Season 13, Episode 16
In one of the show’s biggest swings, the boys are zapped into a Scooby-Doo cartoon — a dream come true for Dean — where they work with the Scooby gang to solve a mystery, all the while trying not to ruin the innocence of Scooby and his friends. The result is FUN. Not only does the episode get points for even attempting such a crossover, but it breaks into the top 20 for its stellar execution in blending the two worlds. —Samantha Highfill
19. ''Mystery Spot''
Season 3, episode 11
Thanks to the Trickster, Sam finds himself in a Groundhog Day-type situation, only every day ends with Dean dying. By the end of the hour, Dean has died more than 100 times, comedy has ensued, and tears have been shed. But after Dean is shot in the parking lot in what feels like an all-too-real scenario, Sam has had enough. He’s emotionally drained and doesn’t care to listen to the Trickster’s lesson about Dean being his weakness. He just wants his brother back, and that’s what he gets. —Samantha Highfill
18. ''Death's Door''
Season 7, episode 10
Bobby is one of the series’ most lovable characters, but all good things must come to an end. Bobby’s troubled past is revealed, but what really sells his farewell is the episode’s final scene. In his head, Bobby relives a night he shared with Sam and Dean, his memory of them fading away. The reaper waiting with Bobby gives him an ultimatum—cross over or remain as a ghost. And while we eventually find out Bobby’s fate, the episode leaves it ambiguous. The seconds ticking away on the reaper’s watch as he waits for Bobby’s decision induce goose bumps. —Jonathon Dornbush
17. ''Point of No Return''
Season 5, episode 18
In the show’s 100th episode, Dean finds himself preparing to say yes to Michael, so much so that Cas gets angry and beats Dean into unconsciousness in a scene that is equally as powerful as it is heart-wrenching. The upsetting interactions continue throughout the hour until, in the episode’s final moments, Dean seems like he’s going to say yes but kills Zachariah at the last moment instead. The only downside? Poor Adam gets trapped into saying yes to Michael. —Samantha Highfill
16. ''The Benders''
Season 1, episode 15
After weeks of the brothers working supernatural case after supernatural case, Sam finds himself kidnapped?by a bunch of homicidal humans. It’s a horrifying twist that plays out over a suspenseful hour when Dean tries to rescue his caged brother before realizing that they’re outnumbered by their biggest foe yet: Psychopaths. —Samantha Highfill
15. ''Two Minutes to Midnight''
Season 5, episode 21
One of season 5’s most interesting throughlines was seeing how the show introduced the Four Horsemen of the Apocalypse. They all made impressive debuts, but none more so than Death. While the episode opens with another Horseman, Pestilence, it’s Dean and Death’s discussion in a Chicago pizza joint that steals the episode. The show’s portrayal of Death is calm and collected, but Julian Richings brings such a powerful presence to the role that his introduction ranks among the all-time best on the show. —Jonathon Dornbush
14. ''All Hell Breaks Loose: Part 1''
Season 2, episode 21
After a season-long build-up to the ”What will become of Sam?” question, Yellow Eyes sticks Sam, and all of his other ”special” children, into a Hunger Games of sorts, which ends when Sam takes a knife in the back and dies in Dean’s arms. All in all, the hour stands out as unlike any other, but most importantly, it marks the first real death of a Winchester brother and therefore, a moment fans will never forget. —Samantha Highfill
13. ''Jus in Bello''
Season 3, episode 12
The hunt for Bela turns into the show’s coolest bottle episode. The incarcerated Winchesters,fight off an onslaught of demons at a Colorado police station. The brothers pull out all the stops from demon traps to salt barriers to keep the place safe, and the demons’ influx makes for one of the show’s most exciting sequences ever. Their struggle ends up being for naught, though; in a brilliant twist, Lilith is introduced and takes out everyone at the station that Sam and Dean risked their own lives to save. —Jonathon Dornbush
Season 8, episode 23
In one of the greatest brother moments of all time, Dean begs Sam to stop the third trial because, even though it will close the gates of Hell, it will also kill Sam. Add in an almost-human Crowley talking about how much he loves Girls (and HBO in general), plus all of the angels falling from heaven, and you’ve got one of the show’s best finales. —Samantha Highfill
11. ''Dark Side of the Moon''
Season 5, episode 16
Sam and Dean have escaped trouble countless times before, but what would happen if they both actually die? Apparently they are sent to heaven, where they decide to use their time in the afterlife to find some connection to God. The brothers’ ideas of Heaven is itself a treat, but their reactions to what one another would find in paradise is just hilarious. ”Moon” is a brilliant way to handle the God question without actually introducing Him, while also dropping in a small but incredible hint that this may not have been the boys’ first visit to Heaven. —Jonathon Dornbush
10. ''The End''
Season 5, episode 4
In an attempt to convince Dean to say yes to Michael, Zachariah sends him five years into the future after a demonic virus has taken over and Future Dean now leads a militia that includes fan-favorite Chuck and orgy-lover Castiel. The kicker? In this world, Sam said yes to Lucifer. The drama culminates when present-day Dean comes face-to-face with Lucifer-Sam, who snaps future Dean’s neck with his foot. Watching Dean try to deny his future is a feat in both storytelling and acting. —Samantha Highfill
9. ''No Rest for the Wicked''
Season 3, episode 16
In another fantastic season close, Dean is dragged to Hell by a pack of Lilith-as-Ruby’s-hellhounds. But there’s much more to the season finale than that. In an effort to save Dean from his inevitable fate, the brothers and Bobby hope to take down Lilith, who’s currently (and in predictably creepy fashion), possessing the body of a little girl and terrorizing her family. Dean is living on the edge of damnation, and he begins to pierce the veil between our world and the fiery afterlife that’s waiting for him. Another show would have saved Dean. Not Supernatural. —Jonathon Dornbush
8. ''Lucifer Rising''
Season 4, episode 22
For all of season 4, Sam and Dean thought they were trying to prevent the apocalypse. In fact, some of heaven’s highest-ranking angels want the end times to happen, and they want the boys to end the apocalypse after it’s begun. Of course, that revelation comes a little too late, just as a demon-blood-drinking Sam accidentally breaks the final seal and unleashes Hell on Earth. And what does that exactly mean? Well, it’s time for the Biggest Bad of all to rise—Lucifer is freed from his cage in one of the series’ greatest season-ending cliffhangers. —Jonathon Dornbush
7. ''Abandon All Hope''
Season 5, episode 10
When Cas, Bobby, Ellen, and Jo team up with Sam and Dean to take down Lucifer, things don’t go as planned. In one of the show’s most heartbreaking goodbyes, Jo and Ellen blow themselves up to kill a group of hellhounds before Sam and Dean finally shoot Lucifer with the Colt, only to realize that, after everything they’ve been through, the Colt doesn’t work on the devil. Instead, one of the show’s strongest dramatic hours ends as the brothers are forced to sit by while Lucifer raises the horseman of Death. —Samantha Highfill
6. ''Changing Channels''
Season 5, episode 8
Thanks to the Trickster, Sam and Dean find themselves trapped in a television world, which the show, in typical Supernatural fashion, uses to poke fun at the likes of Grey’s Anatomy and Japanese game shows, and which culminates in Sam turning into KITT from Knight Rider. Comedy aside, the episode also reveals that the Trickster is really the archangel Gabriel. What’s not to love? —Samantha Highfill
5. ''The Monster at the End of This Book''
Season 4, episode 18
The show once again pulls off one of its meta episodes in excellent style, with the Winchesters discovering there’s been a book series written about their exploits. The books have amassed quite the rabid online fandom, replete with readers writing their own strange and uncomfortable fan fiction. It’s a funny commentary on the show’s audience that impressively never outright mocks them but celebrates their love of the show. But it’s also important for the show’s mythology, as Chuck (who might be God), the man behind the book series, is revealed to be a prophet of Biblical nature. —Jonathon Dornbush
4. ''Lazarus Rising''
Season 4, episode 1
In the season 3 opener, Dean mysteriously appears back on Earth having somehow escaped Hell, and things only got better when we discover how he escaped: He was pulled out by Castiel. Not only did the hour mark the introduction of angels, but Castiel’s entrance is still one of the best moments in the show’s history. —Samantha Highfill
Season 11, episode 4
If Supernatural has proven anything in its time on the air, it’s that this show is not scared to take risks. And more times than not, its riskiest episodes end up being its strongest, and “Baby” is another example of why. An episode told entirely from the perspective of the Impala allowed the show to once again remind fans of what it does best: Brother bonding. And when you take powerful emotional moments and combine that with an unconventional style of filmmaking, what’s not to love? —Samantha Highfill
2. ''The French Mistake''
Season 6, episode 15
In the most meta episode of the series, Balthazar throws Sam and Dean into an alternate reality where they play actors named Jared Padalecki and Jensen Ackles on the set of a show called Supernatural. Things turn sour on set, as series creator Eric Kripke meets an untimely end and a Twitter-loving Misha Collins won’t stop bothering Sam and Dean. (Fun fact: Misha the character writes a tweet on the show that Misha the actor actually tweeted out.) It’s a concept that should be too crazy to work, but the writers and cast make it one of the all-time greats. —Jonathon Dornbush