25 Days of Dean-mas Day 14: Best Dean moments in Supernatural in 2019

We’ve watched all the episodes of Supernatural coming in 2019. It’s time to break them down and look at the 10 best Dean Winchester moments.

There have been 19 episodes of Supernatural throughout 2019. Eight of them aired in Season 15, with the rest airing earlier in the year during Season 14. Now it’s time to look back over each of them for the best Dean Winchester moments throughout 2019.

I’ve tried to be fair and cover the two seasons equally. Naturally, with more episodes in Season 14, you would think that there would be more moments from those episodes. However, Season 15 has certainly been on point by bringing back some familiar faces.

Something I will say is that these are top Dean moments, usually the moments that bring us character development or allow for heartfelt moments that have been a long time coming. Moments that purely showed off Jensen Ackles’ acting won’t be included. If you want to take a look at some of them, you can check out the five moments from Season 14 that I picked out during the summer.

It shouldn’t need to be said, but these moments are only from the new episodes of the series that aired throughout this season. That does cut out a substantial amount of episodes but is only fair on a yearly roundup.

To mark Day 14 of the 25 Days of Dean-mas, here are the 10 best Dean Winchester moments from Supernatural in 2019.

Just as a caution there are spoilers on this list if you’ve not watch all eight episodes of Supernatural Season 15.

10. Singing on stage

While this moment did bring a continuity error (we know that Dean Winchester can’t sing), it brought us a fun moment that was important for the Supernatural fandom. This moment was also important for Dean.

After heading out on a case alone, Dean runs into an old friend. It turns out that old friend now owns a bar and performs songs on the stage. Well, Dean ends up on the stage to sing, with an excellent voice which is nothing like how we’ve heard Dean sing in the past.

This was one of those great moments where two real-life friends got to act together and sing together. It was also a moment where we got to see Dean relax, in an episode that was only going to get darker for him.

9. The vegan/not vegan bacon

After killing Rowena, Sam went into a state of grief and sadness. It was understandable, but Dean just wanted to help. And so, he put together a plate of “vegan” bacon. At least, that’s what he told Sam he had made.

It turned out the bacon was real bacon. Sam found out the hard way. And it brought us a lighthearted moment along with a touching bro moment. Dean made it clear that he wanted to be there for his brother, continuing that knowledge that he’s extremely protective of Sammy. Just in case we needed reminding of it in Supernatural Season 15.

8. Destroying Chuck’s guitar

We had to the Season 14 finale for this next moment. Chuck turns up with a way to help deal with the Jack situation. However, before he gets into the talk, he starts playing a song on his guitar.

Completely fed up with the entire situation and God turning up when he feels like it, Dean took the guitar and shattered it into pieces. As a musician, Jensen Ackles was likely cringing, but this was so perfectly Dean. When Dean is just fed up of people stalling or not helping when they can, he takes it out on them.

In this moment, Dean was also dealing with grief. His fuse was short, and this moment made that clear.

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7. His willingness to lock himself away

Also during Season 14 was a dark moment. Dean learned from Billie that Michael would eventually get out of his head. There was only one way that Billie could see the world not ending completely.

In Supernatural Season 14, Episode 11, Dean made it clear that he was completely willing to sacrifice himself for the world. He built the Ma’lak Box and was willing to put himself in it and drop himself to the bottom of the ocean.

We link back to all those times the Winchesters have offered to sacrifice themselves. However, this time, Dean knew that his brother would be the one to stop him from sacrificing himself; and that’s just what happened.

6. Accepting his fate as a hunter

Jumping back to Supernatural Season 15, we’re looking back at “Last Call.” This episode had some important moments for Dean’s character development in the final season. At the end of the episode, he realized that he wasn’t going to be able to escape the life of the hunter.

But not just that, he fully accepted that hunting was something he was born to do. It was something he wanted to do. After all, he helped people. Even if they weren’t 100% innocent, he would help keep people safe from monsters and creatures in the world—some of them human.

5. Taking control of Apocalypse Michael

Back to Season 14, and we’re looking at “Nihilism.” Apocalypse Michael had left a doorway open to get back into Dean’s vessel when he needed it. That happened in the Season 14 fall finale, leaving us wondering for a month how Team Free Will would deal with this.

Well, we got that in the midseason premiere, which saw Dean in a crevice of his mind within a fake memory. As a fight broke out in this fake memory, Dean had the chance to fight against Apocalypse Michael. And he quickly took over.

“I’m the cage,” Dean stated as he closed Apocalypse Michael in the fridge of the made-up bar. Dean, like Sammy before him, proved that even archangels could be contained, even if just temporarily.

4. Finally refusing to kill Jack

We wondered if Dean was going to go through with it. In fact, we worried he would. Dean had agreed to kill Jack in the Supernatural Season 14 finale. And Jack even got to the point of accepting that he needed to be killed.

However, Dean couldn’t go through with it in the end. Despite grieving for Mary, Dean loved Jack like a son.

We’ve seen him do these things before. He’s considered killing Castiel and Sam in the past, but then not gone through with it. I guess you could say that Jack is now officially a Winchester in Dean’s eyes.

3. Admitting that he does love the life

Supernatural Season 15, Episode 5 brought us a familiar face. Well, sort of. The face wasn’t familiar but the character certainly was. It just took some time to get to that part.

Before we found out that Lilith was back, the girl she pretended to be asked Dean if he enjoyed the hunter’s life. And through all the bad, Dean admitted that he did love it. You could see through the look on his face that he was telling the truth.

And this is where we get continuity in Dean’s personality. Through all the bad, there’s always been more good in saving people.

2. Getting closure with John Winchester

The Supernatural 300th episode was certainly a milestone. We got the full Winchester family back together, by bringing John Winchester from the past to the present day. While history changed around them, John had a chance to make amends with his boys after learning what would happen to him.

We got a moment with Dean and John together. Dean made it clear that while he may have hated the life growing up, he didn’t regret a second of it. The life was what made him the man he has becoming, and it’s a man that, for the majority of the time, we can appreciate, love, and respect.

1. Apologizing to Adam at long last

Finally, we turn to the Supernatural Season 15 fall finale. The show finally brought Adam back into the story, and there was a great twist with Michael. However, it was the end of the episode that delivered this number one Dean moment of 2019.

Dean had the chance to apologize for leaving Adam behind in Hell. He didn’t make excuses or try to give too many reasons. He just admitted that what he did was wrong and Adam deserved much better.

I love that Michael gave Adam that moment. After all, it was more for Adam than it was Dean. However, Dean had the chance to do something he’s not done often: apologize.

What were your favorite Dean moments on Supernatural throughout 2019? Share yours in the comments below.

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