5 best Dean moments from Supernatural Season 14

Supernatural -- "Mint Condition" -- Photo: Dean Buscher/The CW -- Acquired via CW TV PR
Supernatural -- "Mint Condition" -- Photo: Dean Buscher/The CW -- Acquired via CW TV PR /
Supernatural — “Jack in the Box” — Image Number: SN1419a_0049b.jpg — Pictured: Jensen Ackles as Dean — Photo: Diyah Pera/The CW — © 2019 The CW Network, LLC. All Rights Reserved. /

Before looking at things we need to see for Dean in Supernatural Season 15, it’s time to look back. Here are Dean’s top five moments in Season 14.

It’s getting to that point in the year when we start looking at what we hope to see in the next season of Supernatural. Before that, let’s take a look back over the previous season. Each character had some excellent moments. I’m going to look at the top five Dean moments from Supernatural Season 14.

Picking out five moments is never easy, especially from an entire season. There are so many scenes that will stand out for various reasons. And we all love to see something different for the characters, so different moments speak volumes for both of us.

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One thing that I love in writing for characters is to be consistent with the personality but also show some growth. That’s what I did feel we got in Season 14, even when Dean went on a mission to kill Jack. He was scared and we don’t have control over our fight or flight response as much as we like when we’re scared.

I know there are going to be moments on this list that fans don’t agree with. That’s okay! Like I said, we’re all different. What I hope to do is start a respectful discussion. So when it gets to the end of this list, don’t just criticize. Let me know why you feel the way you do, what you wanted to see, and what your favorite Dean moments were instead!

Now let’s get into the top five Dean moments. Oh, and I’m starting with Dean simply because he’s the elder Winchester brother. It really is as simple as that.

Supernatural — “Unhuman Nature” — Photo: Dean Buscher/The CW — Acquired via CW TV PR /

5. Fishing with Jack

When it happened: This was a moment in an earlier part of Supernatural Season 14. During Episode 7, the Winchesters and Castiel learned that Jack was dying. Jack couldn’t hang around the bunker and just accept his fate. He needed to see the world outside. What better way than with Dean?

Why it was so great: The episode gave us some excellent Dean and Jack moments. It did make the latter episodes all the more harder to watch as Dean went on a mission to kill Jack. However, let’s overlook that for the time being. This is about Dean’s greatest hits of Supernatural Season 14.

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When Jack and Dean went fishing, we got a chance to see them bond. We saw the connection they shared. More importantly, we got to see how much Jack looked up to Dean, the one who had struggled to accept Jack as part of the family at first.

You could see that Dean loved this kid as one of his own. He gained that bond that Dean and Bobby had gained once upon a time, this time in reverse with Dean the father instead of the son.

Just the look on Dean’s face as Jack explained why he chose fishing and beer was perfect. Dean didn’t have to say anything at all. Just the sorrowful pride through his eyes was enough.

Supernatural — “Mint Condition” — Photo: Dean Buscher/The CW — Acquired via CW TV PR /

4. Taking on Hatchetman

When it happened: Supernatural Season 14 delivered a Halloween episode to remember. Instead of the traditional Halloween take, we got an All Souls’ Day episode, perfect since the episode aired the day after Halloween. Dean taking on Hatchetman happened in Episode 4, titled “Mint Condition.”

Why it was so great: Halloween episodes don’t happen often because the whole show can feel like Halloween. However, this one was made special because of the whole circumstance surrounding the need for the hunt.

Dean locked himself in his room after Michael let him go. He felt out of place with the Apocalypse World hunters around and Sam in the driving seat—not that he was jealous or anything, he just didn’t feel comfortable with strangers in his home.

This moment gave him a chance to be him. He took on one of his favorite movie villains, delivering some of the corniest moments in perfect style. We could laugh along with the episode, cheering for Dean as he (and in the end, Sam) became the victors of the horror movie.

Those who adore the 1980s horror movies would have certainly appreciated the moment Dean took out the bad guy. It was made all the more stronger knowing that this was a vengeful spirit and Dean was trying to fight it in the classic horror way.

Supernatural — “Nihilism” — Photo: Shane Harvey/The CW — Acquired via CW TV PR /

3. Dean taking control of Michael

When it happened: During the midseason premiere, Sam and Castiel took a trip inside Dean’s mind. They needed to find where Michael had placed him, and it happened to be in a fake memory, one that would repeat over and over again. When Michael stepped into the faux memory, the battle started.

Dean was able to take control of the situation. After all, this was his mind. So, he managed to get Michael locked up and became the cage to hold the archangel.

Why it was so great: The “I’m the cage” line was cheesy, but it fit the situation. It linked back to Supernatural Season 5, when Sam was able to take control of his own body and send himself and Lucifer to the Cage.

Related Story. Jensen Ackles' #1 moment in Supernatural Season 14, Episode 14. light

This time, we got to see Dean take full control and mentally take over the situation. It would take a lot of willpower and it meant that Dean could never let his guard down. We saw this inner strength to him, as he made a decision to attempt to keep the world safe.

This would have a knock-on effect. Dean would have to make a major sacrifice to keep Michael locked away forever, and we just knew that it could never happen! However, watching Dean take full control and attempt to beat the archangel was impressive.

We did see the reaction when Dean lost control. While that was an excellent moment, it’s one of Jensen Ackles’ standout performances rather than a best Dean moment.

Supernatural — “Moriah” — Image Number: SN1420c_0479r.jpg — Pictured (L-R): Jensen Ackles as Dean and Alexander Calvert as Jack — Photo: Jack Rowand/The CW — © 2019 The CW Network, LLC. All Rights Reserved.
Supernatural — “Moriah” — Image Number: SN1420c_0479r.jpg — Pictured (L-R): Jensen Ackles as Dean and Alexander Calvert as Jack — Photo: Jack Rowand/The CW — © 2019 The CW Network, LLC. All Rights Reserved. /

2. When Dean couldn’t go through with killing Jack

When it happened: In the Supernatural Season 14 finale, we saw Dean go on a mission to kill Jack. It was questionable, but at the same time, understandable. It just depended on which side of Dean’s personality you were going to look at.

However, in the end, Dean couldn’t go through with it. He held the gun at Jack, who was waiting to be killed. Dean choose against it, going against everything that Chuck wanted. He took back control. Or did he?

Related Story. Like Dean or not, his character remained consistent in Season 14, Episode 18. light

Why it was so great: It’s not often that we get to see multiple layers to Dean’s character in one moment. In his head, Dean wanted to kill Jack, and I could understand why. This Nephilim without a soul was putting the world in danger. He was using his powers without even meaning to.

However, Dean’s heart knew that killing Jack was wrong. It became this battle between head and heart. After going through all that pain of losing Jack once, Dean knew deep down that he couldn’t go through with killing a boy that he viewed as his son. Soul or no soul, Dean needed to help Jack and killing him wasn’t the answer.

Supernatural Episode 300
Supernatural — “Lebanon” — Photo: Dean Buscher/The CW — Acquired via CW TV PR /

1. The emotional talk with John Winchester

When it happened: The 300th episode saw the return of John Winchester. This was a chance to see some closure to a storyline that had never happened. Even though it was John from the past (from pre-show), we still got a moment of acceptance and closure for all involved.

One of those moments was Dean and John. Dean got the support that he’d always needed. John finally showed just how proud he was of his son after everything that had happened.

Why it was so great: I’ll be honest right now and say I’ve never been a fan of John Winchester. While he may have thought what he was doing was right, he went on a mission of revenge that put his own sons at risk too many times. He forced four-year-old Dean to become a parent to baby Sammy.

However, Supernatural’s 300th anniversary made up for that. John was able to admit his faults. He accepted that some of the things he’d done were wrong but acknowledged that Dean had grown up well because of that.

And this moment isn’t just the No. 1 Dean moment because of John. Dean had his own side. He grew to accept what had happened. He wouldn’t be the guy that he is now if it wasn’t for John, and he wouldn’t change a thing now despite everything that had happened.

Seeing Dean get the closure that he needed was perfect for the 300th episode.

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What were your favorite Dean moments in Supernatural Season 14? Which moments stood out to you for all the right reasons? Share your thoughts in the comments below.

Supernatural Season 15 premieres on Oct. 10 at 8/7c on The CW. Like SPN Hunters on Facebook as we look back at Season 14, before looking ahead at what we’d like to see in Season 15.