When 1010Wins reporter John Montone asked Late Nite’s  announcer Alan Kalter about his 30 years with David Letterman, Kalter highlighted Letterman’s secret of success: ‘He always asked the questions that everyone in America wanted to ask.’

Sounds simple. But  if  that is so, can’t any TV show host just ask those type of simple questions?  How has Dave been able to open up every sort of celebrity, politician, sports star of our generation?  What’s been the secret that has enabled Letterman to have guests entertain the most insane conversations and divulge the most personal aspects of their lives to America all with ridiculous humor?

I’d like to suggest the following:   Dave was always “in character”…

The character Letterman employed with every one of his best interviews is that  out-of-touch, conservative dad, who has little interest in anything other than sports, taxes and movies about baseball.  Basically, he’s the  clueless frum father at a shabbos table who disarms everyone by just asking completely the dumbest and obvious questions about culture, trends, celebrity,  the internet…
but then suddenly you feel compelled to and really want to explain to this out-of-touch grump what’s going on in the world outside.

“Ehhh So what’s this thing they are talking about,  Uhh Tweeting, is  that something on a website?  What do you buy on it?”

Dave To Paris Hilton: “So how’d you like being in jail? … What is it you did?… Do you know what you did?  Something about a license…or something?”

Dave nailed this character. Amazingly awkward,  genuinely unknowledgeable, overly excited feigned curiosity… like your Jewish dad forced to make conversation with one of your friends.

Dave’s talent was pretending to be forced to make conversations with people he pretended to care less about (see interviews with Paris Hilton, Lady Gaga, Lindsa Lohan).  This was his complete genius:  Because when Dave looked down at his notes, checking off with his pencil, and asked  these dumb  seemingly harmless questions to pop culture guests,  it turned the tables. The conversation  flipped  from a standard late-night conversation where a celebrity has some prepared cute story/promo, to putting the onus  on the celeb to explain their existence,  their celebrity, their rehab, their jail time, their sex tape.

When Dave would segue with ” In all seriousness now…”  (crowd cracked up every time he said this – since that was his cue that “You at home are all in on this joke with me”),  he would flip the conversation into the questions all of us actually wanted to know about.  But it was already too late for the celeb, since the topic was already broached with such light basic idiot questions, they had to respond.

This is exactly how that distant frum father at the shabbos table does it too.

He’ll ask general questions about something taboo or foreign,  hinting he has no idea what these things are (meanwhile, he knew exactly what all of these things were) but it got you to open up, to feel safe, empowering you to play the role of the teacher.

“So what’s this online dating?  j-shidduch, or something,  you get their phone number on it?”  and then once he gets the conversation going, he quickly gets to the questions he really wanted to know. “So  is  the problem with the last person you went out with? What really happened there?”

It’s the epic strategy for getting people to open up about things.   Try it.

Rabbis around the US employ this strategy, and it works wonders to get congregants to talk about things, they wouldn’t ever consider talking about with rabbis…all they do is start off by playing dumb about anything…

Dave pretending to be the uncaring, unconcerned and out-of-touch regular Average Joe from Indiana with a set of  simple questions, was the greatest scam of all time.  And it let him unleash his humor and satire upon the most famous people of all time.  Dad’s at home everywhere would watch Dave and say, jesus, that’s exactly what I would’ve asked.

More than that Dave, like that grouchy religious dad, had their opinions on everything. Meaning unlike any other late night host, who loves everyone and everything (Conan, Fallon, Leno, Kimmel) – Dave had people and things he really did NOT  like (Oprah, Dr. Phil, Leno).  So when guests came on, there was this overarching feeling of them really trying hard to get Dave to genuinely like them. Which made for epic drama. (Really only John Stewart has this same list of things/people he can’t stand approach, but he’s too kind /accessible to make celebs/politicians really want to please him like Dave)

Same goes for that aloof Jewish dad.  He had friends of yours he couldn’t stand, and those he loved to bits.    And it is always incredibly entertaining and awkward to see those  friends of yours he hated try to win his favor, or at least conjure up a conversation.

“He is Everyman” said Kalter, at the end of his radio interview on Dave.

In someways I think we all are praying that Colbert takes on this same familiar character when he continues the legacy of being that out-of-touch opinionated “everyman”  – it’ll be hard.  #ThanksDave