Robert Morse, who died yesterday at age 90, managed a neat trick in the two defining roles that bookended his long career in show business. As the Tony Award–winning star of the 1961 Broadway musical How to Succeed in Business Without Really Trying, a role he reprised for the 1967 film version, Morse’s J. Pierrepont Finch became the icon of the Manhattan business world of the early Space Age and the ambitious young men looking to climb its ladder. By the time of the film, the show already felt a bit like a period piece, as the culture had changed dramatically. In Mad Men, from 2007 to 2014, he played Bert Cooper, the crusty elder statesman of . . . an early Space Age Manhattan ad agency full of ambitious young men looking to climb its ladder as the culture around them changed dramatically. Morse was an inspired bit of stunt casting in the role, but he gave it a wonderful performance, and he got to do a musical send-off when Bert died near the end of the show’s run, imparting his lessons to Don Draper:

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There were many other roles in between, including another Tony-winning performance portraying Truman Capote, but Morse will always be remembered for the wry window he provided on one very particular slice of the world. R.I.P.