Most lists were group efforts, executed quickly, per O’Donnell. “Sometimes we’d write 100 of them. Then I’d pitch the best to Letterman minutes before the show. He’d pick a couple, add a couple.” The ...

David Letterman doesn’t retire until May 20, but already the accolades are rolling in as fans prepare to say goodbye to the most influential comedian of his generation. Here’s our top 10 list, ...