The Best David Letterman Moments to Turn Today’s Twenty-Somethings Into Fans

Are the older members of Generation Z and the younger Millennials aware of the fact that David Letterman was once the most hip and happening comedian on all of late-night television? Do kids these days ever watch late-night television? Do they even own a TV?

Those are fair questions for any older Millennial, Gen Xer or, God forbid, a young Boomer who remembers a time when the late-night slot of broadcast television networks was the best place for the kind of hyper-current comedy that the kids of today get from their phones for eight hours each day. 

Though Jimmy Kimmel, Stephen Colbert and the rest of the less beloved late-night hosts of 2024 are fighting hard to keep the medium afloat, there isn’t really a modern-day analog for the kind of cultural power that top late-night hosts such as Letterman wielded on platforms like The Late Show in the 1990s. And, as more and more generations of kids prefer watching inscrutable YouTube videos to engaging with anything that remotely resembles a television show, the zeitgeist is hurtling to a place where both Letterman and late-night comedy itself will be a quaint memory shared only by old fogies in their rocking chairs — kind of like how previous generations felt about Sid Caesar or World War II.

One dinosaur on Twitter recently asked today’s twenty-somethings if the name “David Letterman” means anything to them at all, and the results were mixed. Many young folks derisively responded with some put-down along the lines of “Who is that?” or “Time for bed, grandpa,” but a few loyal Letterman fans fought to remind Twitter — especially Young People Twitter — that Dave used to be the absolute man.