Reading this almost eight years later really makes me laugh. The idea of Roger as "Bad Cop!" He's one of the most beloved characters on the show.

It's perfectly fitting. He went from the mailroom to the boardroom!

He is great in this show as Cooper, the co-owner of the agency. How fitting as his most famous movie role was in How to Succeed in Business Without Really Trying."
"Two more swords and I'll be Queen of the Monkey People." Roseanne

Yes, he plays Mr. Cooper, the better half of the "good cop, bad cop" partners who run the Sterling Cooper advertising agency of which the series relolves about. He's only appeared in two episodes that I've seen so far, and plays a somewhat eccentric chairman of the board type who is still cares about the business, but doesn't like to get involved with the daily tedium.
I heard about the show about a month ago during an interview with its creator of the show on NPR, TiVo'd it that night and have been hooked ever since.