- During one of Late Night's Custom-Made Shows, the audience votes to hear how Dave, guest co-host Dennise, and Jane Pauley would sound if they had inhaled helium.
- ANYTHING involving Larry "Bud" Melman, aka Calvert Deforest.
- When Regis Philbin came out dressed as Shrek. What was funny is that he didn't even bother to act in character, but instead griped about how long it took to get the make-up applied. Letterman's interjections were great too, suggesting that he and Shrek go "get a couple of whores" ("Regis would probably say no, but Shrek is ready!") and interrupting Regis's plug to say "Who cares?"
- The last episode of his run of the Late Show opened with Gerald Ford saying "Our great national nightmare is finally over." A line that was echoed by George H.W. Bush, Bill Clinton, George W. Bush, and President Barack Obama.
- Anything Alan Kalter did.
- When he interviewed the 2013 Indianapolis 500 winner Tony Kanaan, they bring out the Borg-Warner trophy (a giant trophy commemorating all the Indy 500 winners) to show everyone. Dave and Tony realize that they'll never get a chance to be this close to it without security nearby again....so they start touching it all over, capping it with Tony hugging it.
Funny / David Letterman
Let's face it, the ENTIRE FREAKING SHOW can be considered this. But there were a few moments that go beyond this.