Sam is on the road in this Supernatural scene. It's taken from the episode "The Curious Case Of Dean Winchester."
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Dean gets involved with Bobby during the episode "The Curious Case Of Dean Winchester." Strange developments occur from there.
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There's a dangerous game of poker played on the episode "The Curious Case Of Dean Winchester." Dean gets involved in it.
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Supernatural Season 5 Episode 7 Quotes

Sam: It's like Grumpy Old Men.
Dean and Bobby: Shut up, Sam!

Sam: Have you seen you? You look like...
Dean: ... the old chick in Titantic. Shut up.