Almost 23 years before his death, Garry Shandling sat down with David Letterman on the host’s second-to-last night on NBC for a late-night debriefing. The conversation could have been awkward, and definitely went beyond the latest celebrity chit-chat. After all, Shandling had just been offered $5 million to take over Letterman’s time slot, and turned it down. Now, the two men — one leaving a job he no longer wanted, the other unwilling to take it on even for a large amount of money — contemplated the chair as they left it behind.
“Did you ever seriously consider — this all could now be yours,” Letterman said.