One of the problems with the multitude of late night comedy shows (Letterman, Leno, Kimmel, Fallon, O’Brien, Lopez, etc.) is that there’s very little spontaneity. Every bit is rehearsed within an inch of its life. Every guest is pre-interviewed so the host can lead them into the answers or stories they’re prepared to tell. If it’s not on the blue card, it rarely comes up in the conversation.

That’s why I found an appearance by Regis Philbin with David Letterman last week so entertaining.

Before the show, Letterman had come out to chat with the audience as he usually does for a couple of minutes, and for some reason made a reference to Dairy Queen. An Australian woman in the audience raised her hand and asked what Dairy Queen was, because they don’t have them down under. Letterman was shocked, so he had someone on his staff go to DQ and get him a box of Dilly Bars (vanilla pops on a stick with chocolate coating). At the top of Segment 3, he brought out the box of Dilly Bars and gave one to the woman before returning to the desk to introduce Philbin.

Because Regis is a master at small talk who has made a career out of his talent at telling stories about virtually anything that’s happened in his life, and because he doesn’t have any new project to promote, the conversation wasn’t centered on any particular topic. In other words, there were no pre-determined talking points, and no index card full of leading questions.

They talked about Regis spending the holidays at Disney World with his grandchildren, which led to both hosts telling stories about being fired, which led to Dave learning for the first time that Regis had been in the Navy during the Korean War, and on and on. At the end of the segment, Dave pulled out the Dilly Bars, offered one to Regis, and they both bit into the ice cream as the show went to commercial.

When they came back for Segment 4, they were still talking and eating, and the topic of conversation turned to the four people who Letterman considers to be great broadcasters: Oprah Winfrey, Howard Stern, Rush Limbaugh, and Regis Philbin. I doubt that think Letterman watches or listens to all of them every day, but he certainly respects their talents and success — one multi-millionaire superstar admiring four others.

No one said it, but Letterman certainly deserves to be included alongside them. He’s approaching his 30th anniversary on the job, and no one has changed the late night landscape in the post-Carson era as much as Letterman (a fact that no other host would argue with).

Their timing in the segment proves why Letterman and Philbin are both so good as broadcasters and communicators. Remember, they’re having a conversation while they’re eating. You may think it’s easy to do because you talk with your spouse or friends over meals all the time, but it’s not. It’s a lot tougher to do when there are cameras and an audience. Top-notch movies and theater actors hate having to do scenes with food because it gets in the way of the words so easily. But not with these two pros. They know when the audience will laugh, how big a bite to take, when to do takes to the camera, how to needle each other just enough, and how to maintain the verbal flow.