[Cry Me A River]

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as far as I can tell he basically has never watched TV since the mid 50s.

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Well, if we have almost the whole breadth of tv history to pick from...

If his favorite movie is "High Noon", he might really go for "Deadwood". However the language is really raw and he might just consider it vulgar. Maybe pre-watch the first couple eps..

Would he have seen the "Gunsmoke" tv series? What about "Have Gun Will Travel"? Or "Maverick" or "Rawhide"? For something a little more modern, how about "Adventures of Brisco County Jr".

Non westerns...

Law & Order
MASH
Magnum PI
Rockford Files
Monk
ER
Hill Street Blues
Homicide: Life on the Street
Moonlighting
Remington Steele
NYPD Blue
LA Law

Yeesh, could be at this all day...