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.
And Then There Were None - S6-E16
Revealing mistake: Samuel is very much dead, laid out on the table in the canning factory employee lounge, but as Sam stands over him, talking about whether or not it was right to gank him, you can see Samuel's chest rising and falling as he breathes. (00:26:30)
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.