Robert Morse, 'The Best Things in Life Are Free' (Season 7, Episode 7)
The death of Bert Cooper (Robert Morse) was not a surprise, per se, but sad all the same; luckily, Weiner and the show gave the character, and the actor who played him, a lovely send-off. Before Mad Men, Morse was best known for playing the conniving J. Pierrepont Finch in How to Succeed in Business Without Really Trying, and Cooper's exit was a nod to the actor's Broadway past. After his death is announced at SC&P's office, the late co-founder appears to Don in a dream-like sequence, singing the old standard with a chorus line of secretaries behind him. In an interview with Rolling Stone after the episode aired, Morse explained it this way: "It was Bert telling Don: What are you doing? All this shit that you're doing, cut it out. The best things in life are free." Whether Don get Bert's message from the beyond is harder to parse.