25 Days of Dean-mas Day 5: 15 best memories of Dean in Supernatural Season 1

It’s #TBT, so what better time than to take a trip down memory lane? For Day 5 of Dean-mas, we’re looking at the 15 best memories in Supernatural Season 1.

Since the pilot episode, Dean Winchester has been one of the two pillars of Supernatural. To mark #TBT this week and to bring the fifth Dean-mas piece in the Christmas countdown, what better time than now to look back at the best Dean memories of Supernatural Season 1.

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There are certainly many. This was the season we got to meet Dean, seeing his funny but also nerdy side. He was lighthearted much of the time, focused on killing the next monster that he found to protect the innocent people in the town.

We’ve lost some of that nature along the way. That’s what happens when the stakes are raised and you start losing people close to you. It all started at the end of this season with the car crash that nearly took his life—and would have done if it wasn’t for the deal John made—and continued with each death that occurred.

And that’s why Season 1 is so special. This is the season that he could be free. He had a mission to find his father, but he also had his brother by his side and the weight of the world wasn’t on his shoulders.

So, let’s take a look at the 15 best Dean moments from the very first season.

15. Learning about his fear

One of the best things about the first season was getting to know the two lead characters. We found out about their past and got to know their personalities. One of the things we got to learn was about Dean’s fear.

He’s afraid of flying. For those who aren’t, it’s hard to understand what would be so scary about being in something that is unlikely to crash. Yes, you hear about the crashes on the news, but it’s safer flying than it is driving.

Not only do we learn about Dean’s fear, but we also see his protective nature winning over. He’s not letting Sam on the plane with a demon on his own. He’ll face his fear to do it.

14. Seeing him with Cassie

Whether you liked Cassie or not, there is something great about seeing Dean with her in “Route 666.” This was that episode were we saw something deeper to Dean’s personality.

Up to this point, we knew he loved hookups. That made sense considering how he’d be in and out of town. However, this episode reminded us that even someone who travels a lot needs to create connections. That’s something Cassie offered.

13. Knowing something was wrong with Sam

In “Bloody Mary,” Dean knew that there was something Sam wasn’t telling him. Naturally, it was an episode about lies and secrets, but there was more to the story than that for Dean.

This episode of Supernatural Season 1 showed us Dean’s knowledge of Sam. While Dean didn’t know what was going on, he knew that Sam wasn’t okay. And this was more than just Jessica’s death.

As the season progressed, he figured out that there was much more until Sam finally told him the truth. You could see from the beginning that he was a caring big brother and that would be something to continue throughout the series.

12. Managing the human monsters

In “Benders,” we got to see the show take on another form of monster. This time, the monsters weren’t supernatural. They were human cannibals. It was like something out of Texas Chainsaw Massacre.

Dean was able to find a way to take on the humans. While he wouldn’t have initially wanted to do it, he needed to kill in self-defense. He did leave plenty for the cops to deal with, though. Something Dean has always done is try to preserve human life, even if that life doesn’t deserve it.

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11. Finding John’s leather jacket

It’s easy to overlook this moment in the Supernatural pilot, but you’ve got to think about where Dean’s leather jacket came from. He doesn’t start with it.

There’s a moment in the motel room when he finds the jacket that John has left behind. That and the journal are the only items Dean will take with him from the pilot episode—and the journal he picked up at the police station.

Dean is sentimental. It shouldn’t be surprising in Season 7 that he needs Bobby’s hip flask.

10. I’ll pray for you

There was a turning point in Supernatural in the first season when there was a hint of good magic and God. “Faith” brought us an episode of a healer who managed to cure Dean’s heart after being shocked.

It’s soon clear that there’s something evil to it sadly. However, Dean has compassion and empathy for Laila, a woman who is dying of cancer. There’s hope for him when he tells her that he’ll pray for her even though he’s not a praying man.

9. Reuniting with John

After spending almost three-quarters of the season searching for John Winchester, the brothers find him. And what a reunion it is. Dean is just relieved that his dad is alive, and you can see it all in his face.

It’s in this moment that we really understand everything Dean was holding in emotionally. He bottles up everything, tries not to get his hopes up, and tries to manage the emotions as best he can. It’s no wonder he has so many defense mechanisms set up.

8. Dealing with his doppelganger

Supernatural Season 1 gave us an epic moment to see Jensen Ackles’ acting skills. He took on two roles in one of the episodes, and one of those roles was a role within a role. In “Skin,” he had to play a shapeshifter pretending to be him. He couldn’t be the Dean he’d created perfectly, but had to be close enough to have us guessing at one point.

However, there’s a moment that stands out for me in this memory. It’s at the end when he’s killed the doppelganger. He removes the necklace from the shapeshifter and puts it back on.

It would be Season 3 when we’d learn why this meant the world to him, but the moment made it clear that it was special.

7. Dealing with the past

There’s an episode that is often overlooked but is one of the most important of the first season. “Something Wicked” gives us more detail of Dean’s past and his need to protect his brother. We see Dean deal with a monster that his father had faced decades earlier.

Not only did Dean have to deal with a monster from the past, but the guilt of the past. Dean’s understandable selfishness almost led to his brother being killed. That stuck with him and he didn’t make the same mistake again. It continued to develop an understanding for his protectiveness over Sam.

6. Vulnerability returning home

“Home” was one of the best episodes of Supernatural Season 1 for a world of reasons. One of those is a particular phonecall that stands out.

When Dean realizes that he needs to go back home, he calls his dad. John hasn’t been picking up messages but that doesn’t stop Dean from being vulnerable for a minute. Regardless of what John may think of the “weakness,” Dean takes the time to ask his dad for help. It wouldn’t happen often in the show, but this showed just how scared Dean was about going back home.

5. The prank war

We got a lot of funny moments throughout the first season of the series. This was a chance to be more lighthearted than the later seasons, which meant we got a chance to see the brothers just be brothers. Part of that meant the prank war in “Hell House.”

And what a prank war it was. I’m not even sure what the best prank was or who won. All I know is that I loved every second of this episode because of it.

Also, it gave us an insight behind the scenes. Jensen Ackles and Jared Padalecki quickly proved their love for pranking each other.

4. Connecting with Andrea’s son

When the Winchesters went to a small town to deal with a spirit in the water, Dean realized that the young boy had seen far more than he was willing to let on. This boy had been so traumatized that he couldn’t speak anymore, and he shared what he could through images.

It would be Dean who would get the boy to open up with a story about the past. We got to hear Dean retell the story of saving Sam, giving Sam another view of his brother. It was a touching moment that has to stand out as one of the best.

3. Saving people, hunting things, the family business

There are a few iconic lines that stem from the first season. Many of them come from the first two episodes, and that’s the case with this one. While “Wendigo” wasn’t a spectacular episode, it was important for the development of the characters and the overall storyline.

We got the moment at the campfire, as Dean held John’s journal. He’d figured out what his dad wanted him to do. It wasn’t to find him but to continue on the hunter’s journey; saving people, hunting things. John wanted them to continue with the family business.

2. Dad’s on a hunting trip

“Dad’s on a hunting trip. And he hasn’t been home in a few days.” It’s a line that starts of the entire series. Without it, the Winchesters wouldn’t have joined the fight together and we wouldn’t have had 15 seasons of beautiful, perfect moments.

And it stands out as one of the greatest moments. Dean initially tries to remain comedic, but he knows when he has to dial that back. He’s straight up and honest with Sam, knowing that Sam will understand the severity of the situation.

1. Going back for Sammy

Finally, it’s all about the end of the pilot episode. Dean leaves Sam to get back to his normal life, but we knew as viewers that wasn’t it. After all, we couldn’t have Supernatural without the two brothers separate for too long, especially at the start.

So, something was going to get Sam back in the hunt. That something was Jessica’s death, a death that could have claimed Sam’s life too. It was Dean who would save him.

This was a mirror of the beginning of the episode. Dean would be the one to carry his infant brother out of the burning house in the fire that claimed Mary. At the end, Dean would drag Sam out to save him.

What are your favorite Dean moments in the very first season? Which ones stand out for good or bad reasons? Share your thoughts in the comments below.

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