Supernatural has plenty of great moments and episodes featuring the one and only Dean Winchester. Dean's character has many dimensions with his bravado a front for a multi-layer and complex character struggling to deal with the trauma that is his life. It is a testament to Jensen Ackles' amazing acting that he can play Dean so brilliantly with all his various layers with excellent comic timing and heartrending emotional expressions.
Out of the many fantastic episodes that make Dean shine, some are fan-favorites, which showcase why Dean still remains one of the most fascinatingly complex characters on television.
10. LARP And The Real Girl (8x11)
A refreshingly lighthearted episode in a much darker season 8, "LARP And The Real Girl" is focused on LARPing (Live Action Role Playing). The episode mainly centers around Charlie but it also has some of the best Dean moments. Also, Dean and Charlie are BFF goals in this episode.
The best Dean moments in this episode include when he walks next to Charlie, acting as the Queen's handmaiden, and in the end, when Dean gives a speech before charging into the battle of Moondoor as he and Sam decide to LARP after solving the case. It's always fun to watch Dean being carefree because it's a rare occurrence, and this was the first time audiences see him like this after being in Purgatory for a year, which took a toll on him.
9. Dream A Little Dream Of Me (3x10)
Every Supernatural fan knows that Kripke-era 'monster-of-the-week' episodes were excellent and the 10th episode of season 3 was one of them. This episode reveals Bobby's past and why he became a hunter as Dean and Sam take a visit inside his head.
But later in the episode, fans also get to peek inside Dean's head. There is an incredible scene where Dean interacts with his "dark" self. Through this interaction, fans get to learn that Dean has so many issues that he keeps inside and how his upbringing has a lot to do with this. In one shot, the "dark" Dean turns into a demon as he shouts at Dean that this is what he's going to become. This is an accidental foreshadowing because true enough, Dean becomes a demon at the end of season 9.
8. The Trap (15x9)
Episode 9 of season 15 features Dean and Cas revisiting Purgatory after they haven't been on great terms recently. Dean Winchester has had some of the best monologues on the show, but his prayer to Cas in this episode is simply the best. After pushing Cas away for months, Dean finally opens up when he fears that he has lost Cas forever.
He breaks down and apologizes to Cas for treating him the way he did since Mary's death. The vulnerability and the raw emotions on Dean's face make this scene one of the most memorable moments of Supernatural's final season. Even though this is uncharacteristic of Dean, it makes sense that he would finally tell Cas how much he values him only when Cas' life is in danger.
7. Faith (1x12)
This enthralling season 1 episode is a great exploration of life, death, and faith. Dean is on the brink of death in this episode and as a last resort, Sam takes him to a faith healer where things turn out to be shadier than they first seem.
This is the first time fans learn about Dean's readiness to die, which becomes a recurring thing through the rest of the show. He makes a connection with a terminally ill woman, Layla. Dean is saved but Layla isn't and in the end, Dean admits that he doesn't think he deserves to live more than Layla.
6. The End (5x4)
One of the darkest episodes of Supernatural, "The End" is set in the future in a post-apocalyptic world. Dean is sent here by Zachariah to find out what will happen if he doesn't say 'yes' to Michael's plan of possessing him while Sam had said 'yes' to Lucifer. In this episode, Dean meets his future self and even though they are technically the same person, they never feel like that.
Dean's future self shows how cold and numb Dean can become if he loses his brother and the entire world turns apocalyptic. The future Dean doesn't blink an eye in sending his closest friends to their death (even Cas) because he is desperate to save the world. Dean doesn't agree with his future self at any point and he is the one to fight back against him, signifying that Dean, at this point of time at least, cares a lot about his friends.
5. What Is And What Should Never Be (2x20)
In this season 2 episode, a Djinn transports Dean to a world where almost everything is perfect in his life. Dean is living a "normal" life with his girlfriend, his mom is alive, and Sam is engaged to Jessica. At first, he is glad to see his loved ones happy and healthy, but slowly he realizes that everyone he has ever saved in the real world is dead in this one and so, he realizes that he has to go back.
This episode conveyed that while Dean wants to have an apple-pie life for himself and his brother, he also has a savior instinct that wouldn't let innocent people die. Maybe it's because of how he was raised, constantly trying to protect and take care of his little brother even if it came at a cost of his happiness.
4. Tombstone (13x6)
Who doesn't love a dorky geek? Dean has never tried to hide that side of himself but in this episode, that side of him comes through. The reason for this can be attributed majorly to the fact that he just got Cas back and he is elated because of that, which he admits to Sam in this episode.
It also features the iconic scene where Dean and Cas walk together while wearing cowboy hats and boots. This is such a great moment for the duo where fans get to see them acting like best friends who watch movies together and dress up each other as their favorite characters. This episode showed how Dean needs nothing more than his loved ones around him to be happy.
3. Yellow Fever (4x6)
"Yellow Fever" is the episode fans generally think of, when asked about the funniest episodes of Supernatural. Dean gets infected by a ghost sickness, which makes him terrified of everything. The scenes from this episode are some of the funniest Dean scenes ever.
The most memorable moment is Dean screaming as high as possible when a cat jumped out of a locker. Dean Winchester, who is one of the best hunters in the world, getting scared because of a cat would cause any viewer to burst out laughing. It's a guarantee that no fan can watch this episode with a straight face.
2. Dog Dean Afternoon (9x5)
Supernatural is known for its outrageous episodes and "Dog Dean Afternoon" is one of them. This season 9 episode sees Dean acting like a dog and talking to animals. In any other show, this might not have worked but with Dean Winchester, it makes up for hilarious 40 minutes.
Dean almost wages a war with a pigeon, rides the Impala with his head outside the window, makes whimpering sounds, and plays fetch. If only Cas could have used this spell to interrogate the cat in season 8, audiences would have extremely enjoyed that as well.
1. Regarding Dean (12x11)
"Regarding Dean" is solely focused on Dean as he loses his memory slowly through the episode. The portrayal of a person who is slowly forgetting everything about his loved ones and himself is beautiful, heartbreaking, and sometimes even amusing.
In this episode, one cannot help but feel immense adoration for Dean. His child-like antics and his naivety is endearing, especially in the context of season 12 when Dean is constantly feeling a weight on his shoulders. In the end, when he gets his memory back, viewers can instantly see the change in Dean's demeanor. He becomes much more somber and even Sam points out that he was happier when he didn't remember their lives.