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Think you know #Supernatural? Let's put all that time spent rewatching 327 hours of heart stopping broments to the test! Below are six questions to ponder for a few days. These aren't trivia questions that ask for impossibly hard details you never notice because you are holding your breath in terror and/or staring at the fiendishly good looks of our heroes as they battle evil. No, these answers are probably buried deep in your mind. The fun is slowly liberating all that SPNFamily knowledge, consciously or subconsciously, over several days. In other words, we're giving you an excuse to think about Supernatural day and night (like you need another excuse to do that!)!

Think about them when you have to wait for a friend... for a very long time.

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Think about them on those long, backroads road trips.

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Think about them when you're drifting off to sleep at night. 

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Jot answers down on your phone, computer, hunter's journal, or any little sticky note you keep handy. 

1 1 01 Journal

Whenever you call if quits, add up all your points and see how you did! Don't worry, hints are generously supplied to help you get started! 

The Winchester Family Business' Sexy Brainteaser special edition series began with "Brainteaser #6: Sexy Sam". This tantalizingly long brainteaser challenged you to remember all of Sam's steamiest  scenes, from shirtless modeling of his toned physique to his between the sheets exploits. "Brainteaser #7: Sexy Dean" invited you to recall every moment before, during and after Dean's sexual encounters. This edition, "Brainteaser #8: Steamy, Shirtless Scenes" concludes the series by asking you to name all of the remaining shirtless scenes of the Winchesters and their closest friends. For Dean, this edition includes all the times he was shirtless for reasons other than one-on-one time with a special lady. For Castiel and others, we're looking at any time they were shirtless - alone, in public or with someone special. 

However you go about remembering these brief glimpses under the boys' hunter flannel, your lunch hour at work may not be the best place to launch the answer pages! I believe in providing LOTS of pictures to justify the game's points! You have been warned!

Brainteaser #1 (Difficulty Level: Medium)


Let's start our cruise down memory lane with the eldest Winchester. Jeffrey Dean Morgan's John wasn't able to spend very much time with his grown sons, but one hunt resulted in him being momentarily shirtless. To be fair, this scene wasn't so much steamy as it was unforgettable. Name the episode where John Winchester's chest was bared. 

Total Possible Points: 1 

Brainteaser #2 (Difficulty Level: Hard)

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If you aren't new to this PG-13 game series, you may remember from "Brainteaser #7, Sexy Dean Edition" that there were 6 episodes in which Dean removed his shirt to spend time with a lady. There were 5 other occasions, though, when Dean was seen shirtless for reasons other than sex. The first is chilling, but the others? They are definitely steamy! Name these episodes/ situations. 

Total Possible Points: 5 

Brainteaser #3 (Difficulty Level: Medium)

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Shirtless scenes of Castiel were extremely rare. In fact, I only found 3 episodes (out of approximately 147 appearances) in which any iteration of Cas was comfortable enough to be seen unclothed. Two of these scenarios were fun to watch; the third was less so. Name the two times Castiel pleasantly surprised us without clothing. Claim an extra credit point if you can name the 3rd shirtless situation that was painful for both Castiel and fans.  

Total Possible Points: 2 + 1 Possible Extra Credit

Brainteaser #4 (Difficulty Level: Very Hard)


The King of Hell may have lived in a place known for its heat, but he was rarely seen shedding clothing to keep cool. Name the one episode when Crowley actually removed his tailored, black suit, shirt and tie.

Total Possible Points: 1

Brainteaser #5 (Difficulty Level: Easy)

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I recall only one time when Jack appeared without his ever-present, loose-fitting jackets. He looked so young compared to Sam, Dean or the millennia-old Castiel, I compared their ages to make sure he was old enough to be included in our steamy brainteaser! To my surprise, Alex Calvert was almost exactly the same age as Jensen (27), and nearly 4 years older than Jared (23) when they each first appeared shirtless on Supernatural! Name the episode or situation when Jack got a "chilly" reception from his friends. 

Total Possible Points: 1


Brainteaser #6 (Difficulty Level: Hard)

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This challenge is a bit of a departure from Supernatural, but an homage to Winchesters' and friends' shirtless scenes wouldn't be complete without a look at Drake Rodger's John Winchester. Appearing in the Supernatural prequel, The Winchesters, Drake's John steamed up our screens with his shirtless debut in Season 1. Name the episode or situation. 

Total Possible Points: 1


Total Possible Points: 11 plus extra credit

Perfect Score: 11+ Supernatural Aficionado! Clearly I need to make harder games! Fess up: How long did it take you to get them all right?

Supernatural Expert - 9 or 10

Supernatural Authority - 6 to 8

Supernatural Fan in Training - 0 to 5. You may be the smartest player in all categories because your homework is to watch more Supernatural

Use the page menu above to see each Brainteaser answer key or Click "Next" to scroll  the answer pages.

Brainteaser #1 Answers

Name the episode where John Winchester's chest was bared. 

2.01 "In My Time of Dying"
- Sadly, doctors weren't able to save John after he traded his life for Dean's. Understandably, the emotional impact of his sacrifice may have distracted you from noticing that his shirt was open for the entire scene. 

2.01 0997 John dies

Click "Next" to see the next answer page.

Brainteaser #2 Answers

Name 5 episodes or situations when Dean was shirtless for reasons other than indulging sensual desires.

1. 2.01 "In My Time of Dying" - This answer was probably easy if you remembered John's shirtless scene for Brainteaser #1. Dean's bare chest may have been the last thing you noticed as you watched the horrifying scene of him dying in his hospital bed, but medical emergency still required the necessity of being unclothed. 

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On second thought, maybe you did notice...

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2. 1.06 "Skin" - True to its name, "Skin" gave us a transformation sequence that featured chest and back views of Dean's sleek physique... 


stretched and taut as one gets when disrobing.

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It wasn't a pleasant experience for Dean's doppelganger, but fans didn't seem to mind the bare-all exposition of monster lore. Technically, it was a shapeshifter copying Dean's body, but the view's the same. 


3. 1.11 "Scarecrow" - Dean is sleeping peacefully in the next bed without his ever-present tee when Sam gets a wake-up call from their dad. Once Dean hears who's on the phone, he snaps to attention, giving us a precious few seconds of his bare-chest sleeping attire. 

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4. 4.01 "Lazarus Rising" - It was exactly two years before we would again see Dean's body for reasons other than being with a special someone for the evening. After he was raised from perdition, fans joined Dean in being awed by his unscarred, lean, muscular abs. Amusingly, The WFB writer at the time saved this screen capture under the witty, double-meaning title, "Dean's Perfect Chest". 


5. 9.18 "Meta Fiction" - Mercifully, Robbie Thompson broke a 5 year drought of gratuitous nudity with literally a shower of slow, steamy shots of Dean contemplating the new defacement of his otherwise perfect structure. 

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The view lingers on his shoulders...

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and neck...

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and then trapezius muscles...

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and all that cascading water...

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washing over Dean's troubled mind... 

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but it wasn't enough to rinse away the mark that colored Dean's forearm.

9.18 0063 Arm MoC

So Dean pondered...


and considered...


and ultimately lived with the burden of his fate. 

Click "Next" to see the next answer page.

Brainteaser #3 Answers

Name 2 episodes when Castiel was shirtless. 

1. 9.01 "I Think I'm Gonna Like It Here" - After a bloody battle with an angel (who could have been a friend if things had turned out differently), Castiel very logically concluded that he needed a laundromat to clean his one and only change of clothes. This led to several humorous, awkward and somewhat refreshing minutes of him disrobing in public. First, his back was exposed when he removed his shirt...

9.01 1577 Castiels back

then things quickly progressed from there...

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as his trousers and trenchcoat were cast into the wash.

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Ultimately, he didn't end up cleaned and pressed because he decided his last few quarters were better spent on food. 

9.01 1599 undressed thinking

2. 9.03 "I'm No Angel" - In one of Supernatural's more controversial, disturbing stories, Castiel, having lost his grace and now human, spent the night with a woman he believed to be a Good Samaritan.

9.03 0952 arm wound

9.03 1072 Castiel April in Bed

The Enochian warding sigil tattoo that is partially visible on Castiel's lower ribs hid him from angels and gave him a dark air of a mysterious past. Sadly, they were also indirectly responsible for the cruel end to Castiel's one night of bliss. 

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Unbeknownst to him, April was a reaper who used sex to lower Castiel's guard, making him vulnerable to her attack. Similar to when Dean slept with an Amazonian woman who needed a partner to impregnate her, Castiel was an unwitting victim being used as part of a larger scheme.   

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At least he, and fans, got a few minutes of happiness before the scenes of his body being tortured turned his (and our) Heaven into Hell.  

There is one more shirtless scenes for Castiel. In 5.18 "The Point of No Return", Castiel carved a banishing symbol into his chest with an angel blade. Those pictures are gruesome and bloody - and certainly not steamy - so I chose to leave them to your extended research! If you're interested, you can check them out in our episode photo gallery (at the link above) and give yourself 1 extra credit point for remembering that episode.

Click "Next" to see the next answer page.

Brainteaser #4 Answers

Name the one episode that gave us a rare view of the Crowley who hid underneath his tailored, black suit. 

9.23 "Do You Believe In Miracles?" -
Crowley's indulgence may not have been in the steamy part of the spa, but it sure looks hot!

9.23 0235 Crowley massage

9.23 0237 Crowley Massage

Click "Next" to see the next answer page.

Brainteaser #5 Answers

Name the one episode that showed Jack's bare essentials.

13.01 "Lost and Found" - Jack was brought into this world the same way as any other human being - naked. Thanks to his mom, though, he wasn't entirely helpless. 


Jack's mom told him he needed to grow up quickly to defend himself against those who wanted to harm him, so when Sam found Jack moments after his birth, Jack was already a teenager.

13.01 0038 Jack naked eyes glowing

Like Adam in the Garden of Eden, Jack didn't know he was naked, though,...

13.01 0206 Jack naked in forest

until local townspeople noticed him...

13.01 0371 Jack naked staring

and told him he was different, shredding the veil of innocence that accompanied his birth.
13.01 0382 Jack naked confrontation

Click "Next" to see the next answer page.

Brainteaser #6 Answers

Name The Winchesters episode in which Drake's John steamed up our screens with his shirtless debut.

W1.04 "Masters of War" -
In any universe, a Winchester in prime, fighting shape is a natural wonder.  

1.04 0181 john in sun

Sparring with Mary to be able to take on whatever monsters they might encounter, 

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John's Marine training kept him in peak condition. 

1.04 0168 John full of grass

Semper Fi!

How did you do? Did any questions stump you, or remind you of great moments in Supernatural's history?  Please share in the comments below!

Some answers verified with 
Pictures courtesy of The CW and Home of the Nutty

Want more Brainteasers? Find them on The WFB's Game Page! How about Crosswords, Word Search, Trivia or Bingo? The Game Page has hundreds of Supernatural puzzles. Bookmark the page and play them all! You can also play #CaptionThis every week! Caption or vote on your favorite Supernatural moments. Entries are hilarious!