9. Letterman's 'Hurricane Sandy' Show (October 29, 2012)
As Hurricane Sandy was preparing to make landfall, the Late Show faced an unusual dilemma: The crew was at the Ed Sullivan Theater, but it wasn't safe to have audience members. So how do they put on a show? The delightful answer was: Like it's one big game of dress-up. With no crowd, Letterman, Paul Shaffer and his staff went about throwing together something very silly and barebones, bringing on true-trouper guest Denzel Washington to chat for a bit. When jokes bombed, the silence in the studio was a brilliant ironic counterpoint, and the whole enterprise a nice visual illustration of Dave's self-deprecating wit. "I'm so sad that 500 people couldn’t be here to enjoy this," he sarcastically lamented to Paul at one point. The whole thing felt like a brilliant meta-comedy throwback to his Late Night years.