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“Most surprising moment that caught you off guard?” u/PumpkinImpossible inquired on the r/Supernatural subreddit. The first response came from u/mmahv, who simply answered, “Well I was pretty sure there was NO WAY Dean was really going to hell in Season 3 so…”
At the end of Season 2, Jake Talley (Aldis Hodge) kills Sam. In an attempt to save his brother, Dean enters a crossroads deal to bring him back. The demon only gives Dean one year because she isn’t supposed to be making deals with the Winchesters.
Due to the buildup throughout Season 3, most fans likely expected Dean to escape Hell’s clutches. After all, the brothers survived some truly questionable situations throughout the series thus far, and on top of that, in the early seasons of “Supernatural,” the idea of going to Hell seemed so final. But then came the Season 3 finale “No Rest for the Wicked,” which ends with the clock running out on Dean’s deal. The final shot sees him strung up in chains and screaming for help – his soul has been sent to Hell.
Although this all aired back in 2008, and both brothers went on to experience much worse, the initial shock of Dean going to Hell still hasn’t quite worn off. It taught “Supernatural” fans a vital lesson: Anything can happen and the Winchesters, despite how important they are, are not safe.
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