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Welcome back to The WFB's "Top Six Favourites Episodes", this time for Supernatural season five. These episodes are still, to this day, nearest and dearest to my heart. They are my comfort episodes, the ones I go to when I need a laugh or a cry or the comfort of an old friend. 

Before you read my list, make your own list of season 5 favourites! It will be fun to compare your unbiased choices (before you are unduly influenced by my memories or picks) to mine.  If you're joining Nightsky and The WFB in the #SPNSummer2019 Rewatch, or rewatching at your own pace this hiatus, the episodes should be fresh in your mind! Save your list then, because you'll need it for TOP 100 Episode challenge that The Winchester Family Business is running all hiatus! Nightsky reveals her Top 6 season 5 favourites after mine, so you'll have two WFB staff lists as a comparison!

So without further ado, here's my list of Season Five Favourites! The list is by order of appearance only, as they all are equal in their importance to me. 

1) The End

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Dean gets a call from Castiel, who wants to meet up, but Dean needs sleep and will contact him later.    


Castiel tells Dean he'll wait right here, but Dean's already hung up.       

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Sam informs Dean that Lucifer wants Sam as his vessel.  Sam wants to get together to go after Lucifer.       

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Dean tells Sam that it's better if they stay away from each other indefinitely.   

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Zachariah sends Dean five years into the future, to show him why he needs to say yes to Michael.    

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The future is bleak. The Croatoan virus and demons have over taken the planet.  

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Dean finds the Impala (Baby) abandoned and pretty much destroyed.      

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Dean meets up with future Castiel, who is now mostly human and a hippy.      

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He also meets up with his future self,  which was not a pleasant experience.   


Worst yet, he meets up with future Lucifer, who is now possessing Sam's vessel.    


Zachariah returns Dean, hoping he will now say yes to Michael, but Dean says 'Nah' instead.  Before Zachariah can capture Dean.....                         


...Castiel brings Dean to him. 'We had an appointment.'                      

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Dean contacts Sam and they meet. Dean feels it's better they stay together. 'We keep each other human.'           


2) Curious Case of Dean Winchester

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We are introduced to Patrick, a warlock, who uses his craft to play a different form of Poker.  The payment is not in money but in years. If you win, you become younger. If you lose, you become older.           


Bobby plays, loses and ages 25 years.                                 

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Dean then plays and bets fifty years, 25 to restore Bobby and 25 for him.   

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Patrick restores Bobby and then they play.                   

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Unfortunately Dean loses and is now 50 years older.        

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Sam gets to watch 'Grumpy Old Men' live.  

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While Bobby and Dean work on a spell......            

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Sam  plays against Patrick.  Luckily, Sam wins and......                            

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...restores Dean to his younger self.   

3) Changing Channels

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Sam and Dean get pulled into Television Land and are forced to play their role in various genre of TV shows, like a cheesy 80's  sitcom....        

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doctors in a medical drama...          

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forensic investigators...       

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contestants in a game show....       

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crime fighters with our very own Sampala...     

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and even actors in an embarrassing herpes commercial.   

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All brought to us by our beloved Trickster, or should I say Archangel Gabriel.     

4) Abandon All Hope

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This episode give us our introduction to Crowley and the return of the Colt.      


Team Free Will gather to make what will hopefully be a final attempt to kill Lucifer.      

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While Ellen, Jo and the brothers search for Lucifer....        

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... Castiel investigates the number of reapers in town.               

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Demon Meg makes an appearance with some Hell hounds.               

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Jo become mortally wounded. They all take refuge in a Hardware store.         

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Jo comes to terms with her fate and tells them to make bombs and she will detonate them and kill the hell hounds so they can escape.      

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Sadly, Sam and Dean say goodbye to Jo so they can leave on their mission. However, when Ellen comes to say her goodbyes ....

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Jo realises her mom isn't leaving. Ellen couldn't leave her only child to die alone.  

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Ellen stays until Jo passes on. Ellen then lets the Hell hounds in and blows them all up.   

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Sam and Dean meet up with Lucifer and shoot him with the Colt, however it doesn't work.  Castiel comes and rescues the boys.


Back at Bobby's they give a hunter's burial to Ellen and Jo by burning the group picture.      

As a side note: To this day, ten years after its original airing, I have not been able to re-watch this episode. With being a mother, the concept of losing my daughter, my only child....all I can say is this episode hit me hard. I cried for days, weeks, months even years after the airing of this episode.

5) The Song Remains the Same

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Anna goes back to 1978 to kill Mary and John in order to stop the boys from being born.    


Cas sends Sam, Dean and himself to 1978 to stop Anna.     

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However, transporting nearly wipes out Cas' powers.     

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Sam's expression of meeting his mother for the first time and seeing his dad before the effects of his hunting years is both heartbreaking and adorable.     

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The boys introduce themselves to John as Mary's distant cousins. John is eager to know more about the boys but Mary wants them out.       

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John is lured to his work and gets jumped by Anna, but Mary and the boys show up to battle it out. Sam uses the vanishing sigil to send Anna away, so they can escape and hide out.    

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John is now informed that 'monsters' are real and that Mary and the boys are hunters. This leads to a somewhat funny but awkward 'Winchester Family Road Trip' ...."Shut up all of you! Not another word or so help me I'll turn this car around!"     

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Once they take refuge in Mary's family hideout, Sam and John have a moment to talk. Sam shares that they lived the hunters life but he also understands the life his father had to give them.      

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Dean and Mary have their own chat. Mary is now informed that Sam and Dean are her sons and that they are from the future, and why Anna is trying to kill them.  We also learn that Mary is already pregnant with Dean.                           

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Anna and Uriel find the Winchesters and a battle breaks out. Sam is killed and John is greeted by Michael, who takes John as his vessel. John sends Uriel away and kills Anna. He tells Dean that nothing will change. Mary will die and they will be Michael and Lucifer's vessels.  Michael heals Sam and sends them and Castiel back to their present time. 


6) Dark Side of the Moon


Sam and Dean are woken up by hunters. They are there to kill Sam for starting the apocalypse.

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Sam is shot and killed first........  

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...and then Dean.      


Dean wakes up to find himself in the Impala with a very young Sammy, excited about shooting off fireworks.   After a beautiful moment with the two....Dean finds himself back in the Impala, with Castiel talking to him through the radio, telling him to follow the road and he will find Sam. 

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Dean finds Sam in his own memory. Sam is eleven and is having his first real Thanksgiving dinner with a school friend's family.           

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Castiel is able to contact them through the TV and warns that Zachariah is looking for them, as he needs them alive. Castiel wants them to continue following the road until they find Joshua. Joshua talks to God and Castiel hopes Joshua will get God to help them.   

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However, the boys find themselves being flipped from one memory to another. Being back home ......                      

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....when they were little and Mary was still alive...                     


and when Sam had run away and lived in a trailer with a dog.     

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When they find themselves back on the street going into another memory, Zachariah finds them, but they manage to escape thanks to an old friend....            


........Ash!  Ash is running the Roadhouse and has been keeping in touch with another old friend...           

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...Pamela.  After catching up, Ash helps them leave to find Joshua.     

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However, Zachariah catches up to them and threatens them to get them to say yes.    

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Luckily, Joshua rescues the brothers and informs them that God wants them to leave Him alone. He will not help.           


This news is devastating to Castiel and the brothers. Dean's faith is gone and he tosses away the 'amulet'.               

Those are my top favourites for season five! As promised, here are Nightsky's "Top 6 Favourite Episodes" for season five, in order of preference:

  1.  "Swan Song"
  2.  "The End"
  3.  "Changing Channels"
  4.  "Abandon All Hope"
  5.  "Point of No Return"
  6.  "Dark Side of the Moon" 

Now it's your turn!  Which episodes make your top 6? What surprised you, either by inclusion or exclusion, from my or Nightsky's lists? Make your lists now, if you didn't before you read our favorites. You're going to need them for WFB's Ultimate Top 100 Hiatus Challenge!

Having fun comparing favorites? Keep going with Season 6's Top 6 List

If you missed seeing our earlier lists, catch up on:
Top 6 Favourite Episodes, Supernatural Season 1
Top 6 Favourite Episodes, Supernatural Season 2
Top 6 Favourite Episodes, Supernatural Season 3 and so on! Each season has a link to the next season's list! You can follow along through the entire series! 

Enjoy The WFB's many other Supernatural Top 10 lists, always available on our Tags Page!

Please share your thoughts below!