Sam (Jared Padalecki) and Dean (Jensen Ackles) discover a he-witch (guest star Hal Ozsan) is running a high-stakes poker game where the currency is life years instead of money. Bobby (Jim Beaver) sees the game as a chance to get out of the wheelchair and bets 25 years, but loses. As Bobby begins to age rapidly, Dean steps in to save him but also ends up turning into an old man, leaving Sam holding the bag for their survival. Robert Singer directed the episode with teleplay by Sera Gamble and story by Sera Gamble & Jenny Klein.
I’ll admit right now I went into watching The Curious Case of Dean Winchester with a large grain of trepidation. Not because of the plot line though, because I was fairly certain that Sera Gamble as one of Supernatural’s veteran writers would be able to create a credible storyline around the premise of a he-witch with the powers to give to or take years from a person’s life. What I had the trepidation about was knowing that instead of putting the highly talented Jensen Ackles through the aging process via special effects make up, the studio had chosen to send out a casting call for an older actor to play the part of seventy-some year old Dean Winchester.
The way I saw this,we had a fifty-fifty chance of the casting director making a brilliant choice such as was made when young Ridge Canipe was chosen, not once but twice to portray a younger version of Dean Winchester (most notable as 12 year old Dean in Supernatural S3.08 A Very Supernatural Christmas), or what was in my opinion an unmitigated disaster in the choice of casting Brock Kelly to play eighteen year old Dean Winchester in Supernatural S4.13 episode After School Special.
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