Question: How old are Dean and Sam in season 9?
Answer: Dean is 33 and Sam is 29 around season 9.
Answer: Early 30's. The flashback shows them 22 years earlier when their dad says "Dean take your brother and go." Dean looks to be 5 and Sam is just a baby.
Hell House - S1-E17
Visible crew/equipment: When Dean, Sam, Ed and Harry have just shot Mordechai, the cameraman's arm is visible on the right-hand side of the screen. (00:33:30)
Dean Winchester: Driver picks the music. Shotgun shuts his cakehole.
Trivia: The inscription on John Winchester's gun is Latin, translating to "I will not fear evil."
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Answer: There are 4 years between Sam and Dean so Dean was 4 or 4 1/2 when he took Sam out of the house. Sam was 6 months.