David Letterman, Jerry Seinfeld, Barack Obama & The Cool Kids’ Table

When it’s all said and done we usually wind up right back in high school.  None of us ever forgets who we were back then no matter how much we might like to.  And that memory influences how we behave decades down the line in our professional lives, our love lives, and as we saw in 2016 our political lives.  Rational and engaged political actors have been racking our brains over the Trump phenomenon for a full two years now.  Closeted racism helps explain some of it but it just doesn’t cut it no matter how convenient the truth may be.  We have tried to figure out how in the hell a train-wreck, tire-fire, comb-over clown like Donald Trump can maintain a durable 38% approval rating in a supposedly civilized society and first-world democracy.  Professional pundits tend to focus on how LOW that number is but they are looking at it as trained analysts.  To an outsider who just follows politics every day and votes in every election 38% sounds like a SKY HIGH achievement when you reflect on this guy’s performance since he became a permanent cast member in the dramatic comedy and Greek tragedy that American politics have become.

The idea that roughly 4 in 10 Americans approve of a president who is a shameless Putin fluffer, pussy-grabber, race-baiter and scandal jockey is INSANE.  I’m STILL not buying it.  I am not doubting the pollsters’ findings, but I am challenging the information being reported to them by those they are surveying.  Something else is going on that explains what is REALLY motivating that 4 in 10 and I have finally figured it out.


I was binge watching Netflix to escape the irritating coverage of this stupid “Nunes Memo” story and the wall to wall pre-Super Bowl hype when I picked up a new perspective on this dynamic.  It immediately took me right back to high school.  I realized that Barack Obama is the easy-going, self-assured cool guy everybody likes and Donald Trump is the entitled, loud-mouthed prick who hates that guy and stands on his sense of entitlement to grab any attention he can get.  And he gets his share because of it.

I came to this realization watching the incomparable David Letterman’s new Netflix series “My Next Guest Needs No Introduction.”  The episodes are extended format intimate interviews and retrospectives, with the big hook being that everybody appearing on the show is an “extra special guest” caliber heavy hitter.  And his very first show featured none other than Barack Obama.  The audience did not know who the special guest was going to be and when Dave introduced him, the roar from the crowd was so loud it seemed like the roof would blow right off of New York’s City College auditorium.  It was an awesome and uplifting spectacle.  Of course the interview was fantastic, with Dave’s signature wise-cracking and Obama’s signature comedic timing and entertaining rapport reminding us what it was like to turn on the television and see THAT every day instead of the bitter, bloated, orange-faced blow-hard we have now.  The very same thing can be said for Obama’s guest appearance on Jerry Seinfeld’s incredibly enjoyable series “Comedians In Cars Getting Coffee.”


Obama is just cool and Jerry was clearly loving the access he had to hang out with #44.  If you are waiting for Dave or Jerry to make time to hang out with Donald Trump I have a word of advice: Don’t hold your breath.

Let’s be candid:  Obama is young.  He is handsome.  He is fit.  He is dapper.  He is both smart and wise.  He is eloquent to the point that it stands out regardless of who else may be sharing the stage with him.  He is undeniably one of the greatest success stories in American history.  And despite all of that he is always humble, composed, relatable and human- going out of his way to make sure that anybody watching sees a genuine connection to themselves.  His popularity is based entirely on positivity and inclusion and will endure forever for that reason.  He has danced with his daughter while Prince rocked his guitar for him at a private party.  He has danced with his wife while Stevie Wonder brought the crowd to their feet banging his keyboard.  And he has gamely danced and laughed with our girl Ellen while she lost her unshakable cool to Flo’ Rida.


His magnetism is unmatched in any politician in any era and anybody who is down with Obama feels like they are at the ultimate cool kids table.  Everybody is there: the despised Hollywood “in-crowd” and the maligned New York “elites”, stars of the arts and sports worlds, select foreign leaders, noteworthy scholars as well as our foremost leaders in innovation and commerce.

But there is a group of people who would love to be a part of the party who have locked themselves out.  Those who have always felt duty-bound to oppose Barack Obama are deeply jealous and resentful of being on the outside of such an amazing phenomenon.  They desperately want one of their own to rally around- somebody exciting and charismatic to make them feel like THEY are at the cool kids table.

So Trump came along and offered them a taste of delicious revenge.  He has been a TV star for many years and he chose to sit with THEM and give the finger to all of the cool kids he’s been hanging around with all this time.  He’s using them of course but they can’t be bothered with that inconvenient truth.

trump fan with scared face

They are going to hang on to him and savor him like the last peanut M&M in the bag no matter what he says or does.  They have never felt like this before- at the center table at the invitation of the big man on campus.  They have screamed to feel relevant for so long- stuck largely in “fly over country” and feeling ridiculed for their Red State sensibilities.  The few “celebrities” they could get to sit with them are either old as hell (Clint Eastwood) or entirely inconsequential on the scene (Dennis Miller).  So the Trump phenomenon certainly has nothing to do with policy.  It certainly does have something to do with race but not quite as much as we’d assume.  It has a whole lot to do with feeling good- even feeling cool for once.  Trump is the one who gave them that feeling and they never want to feel like outsiders looking in again.  That, my friends, is how you get to almost 40% of the people to approve of you no matter how poorly you actually perform.  Take them back to high school and let them be the cool kids.  And just like back then, the kids that want to be in will stick like glue to the one who let them in long after they realize for themselves that he is a jealous, selfish, entitled, loud-mouthed prick.

∞ π

5 thoughts on “David Letterman, Jerry Seinfeld, Barack Obama & The Cool Kids’ Table

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  1. It is unbelievable that political internet media has fallen so far. You could distill this entire article to “Trump is self-evidently a terrible choice for president” and “Trump isn’t a cool kid man”. Regardless of what you will say, I will have a hard time believing that you base your political decisions on anything besides perceived hipness after reading this.

    You seem potentially somewhat intelligence. If you are, then why would you create a website that is supposedly an attempt to actualize change, and then engage in a type of pseudointellectual non-analysis that pervades internet political media today–part of the reason that Trump was able to win? It reads like a blog.

    Trump was elected because the Democratic Party has succeeded in alienating a portion of normally Democrat-friendly white voters.

    As a Democrat or left-leaning voter, whatever, you want to win elections? You can’t allow your party to ignore the economic plights of the white working class. You can’t allow media outlets friendly with your causes to get away with constantly criticizing white Americans, regardless of how much you think they deserve it. I don’t care how justified you feel that you are–your party is going to struggle to consistently win elections if you do not temper the charged social/racial rhetoric.

    Do you believe that fault falls entirely on white Americans for allowing this to happen? For allowing a guy like this to win?

    Progressives were in the position to get what like no other point in American history, and they managed to fuck it up.

    By writing pseudointellectual, emotionally-driven drivel that is part of the trend for popular internet political media, you are accomplishing nothing. You are not doing anything besides potentially alienating white voters–which you need, whether you like it or not. You are not converting anyone. You are contributing nothing insightful, you are creating dime a dozen material, and you are ultimately contributing to the sabotage of your own political goals.

    Pick one: you can firmly win elections, or you can go full-boar championing your progressive social politics.


    1. Thank you for reading and weighing in. First, this reads like a blog because it is a blog. And second, I think you should read more than one piece of my writing before reaching these conclusions with such certainty. But that’s your right. Just know that my intellect is not subject to your judgment or assessment. My writing is. If it sucks to you then that’s cool. Anybody who writes for public consumption has to accept that.
      I’ll be glad to visit your blog and read what you’ve got to say on the issues that I address.
      As far as the elections go, the trends are not favoring your position. From the results in Virginia, Alabama and now Pennsylvania Trumpism looks like it is headed for the showers at half-time.


    2. My first reply was very measured and polite but after re-reading the piece you are criticizing, you’ve got a bit more coming to you. First of all, if you “can’t believe how far political internet has fallen” then you obviously have spent no time reading politics on the internet in the last ten years. The worst material that you can imagine finds its home right here in cyberspace- threats of violence, racist attacks, sexist threats and everything in-between. What I have written here is very mild and measured by comparison. If this offends you then you need to stay off the internet altogether because the hits are just too hard for you. You obviously cannot handle it so check out before your feelings get hurt any worse. How you even wound up visiting my blog is a mystery.

      Evidently you do not know what I am trying to “accomplish” with my writing and I am certainly not trying to “convert” anybody. If somebody out there needs me to court them along racial lines then they need to go looking someplace else. My blog is read by people from everywhere in this country and in nations all over the world. I don’t need the approval of anybody who needs a special message because they are white and have to work for a living. They are the one with the problem and I have neither the time nor inclination to solve it for them.

      And the next time you want to question a person’s intellect in writing, run a spell check to make sure that your grammar is correct. And then write down your own ideas, impressions and perspectives and publish them for the entire world to see. Find out exactly what you can “accomplish” or who you can “convert” to whatever cause you are advocating for. It occurs to me that with all of your yammering it is impossible to tell what you stand for other than objecting to what I have written.

      If you have any capacity self-awareness, that should bother you. Almost as much as realizing how foolish you sound framing another person’s political activities down to two options. So you do you, and I’ll do me.


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