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John Slattery was from Homefront the show on ABC that introduced the world to Kyle Chandler. It was in the early 90s and Slattery already was grey.

Cranston was from Seinfeld. Giancarlo Esposito was in New York Undercover, but also on GL back in 1982. There are clips, I feel like I've always known him, but that's because he was on Sesame Street.
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Mad Men · Primetime Shows