Conversation with a Purpose

David Letterman talks to former President Obama and Congressman John Lewis in a powerful conversation of self-discovery

J. King
Casual Rambling
7 min readJan 19, 2018

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from The Today Show

I recall asking my grandmother as a teenager why the Bible skipped just about all of Jesus’s adolescence. What was the most important divine human being doing in that unrecorded time?

I take heed from a novelist and video game critic, Ben Croshaw, who spoke on good storytelling. Croshaw said to something to the effect of that good books provide the reader with the most interesting content within a story (paraphrasing his words). I agree with that sentiment.

Whatever Jesus was doing in his early years wasn’t important enough to the Gospels or God to put in the Good Book. But as I sit here in my tiny room, next to a makeshift closet held loosely together my mini-black PVC pipes, I ponder a different question. I ponder two questions, actually.

First, did Jesus ever sit down by a fire with some of the disciples and shoot the shit about his thoughts on women, or politics, or camels?

Second, is Barack Obama aware of the impact his legacy will leave on young Americans for generations to come?

Many things struck me in David Letterman’s conversation with former President Barack Obama, but one remark stuck out above the rest.

Letterman asked Obama about Michelle’s impact as the First Lady. Obama’s response told me why I believe Barack Obama will be recognized as the most important leader of our generation.

Barack said Michelle realized, before he did, that there’s a lot of power in making change culturally than through legislation. That cultural change comes through conversation. Conversation with a purpose.

Mr. Obama caught on to it himself, reaching out to young people. He talked sports with Bill Simmons. He hosted Stephen Colbert’s Comedy Central show. Barack Obama had conversations that mattered to the social conscience of America. The deep inner workings of legislation are BORING. Hell, I remember my first job as a clerk for the student government of my college. There were endless pointless meetings talking about boring shit. And that’s pretend government!

The reason television shows like House of Cards and Veep exist is because the best part of politics is the dramatization of human interaction. Sure we can understand policy at a basic level (meanwhile self-proclaimed experts fly in from every corner of the internet to flex their policy genius), but most self-effacing intelligent human beings know that our knowledge of policy is vague or at the very least limited.

Talking policy is unsatisfying anyway outside of some momentary catharsis. Politics isn’t a dinner table conversation unless it affects those at the table enough to say something. But there are so many more entertaining conversations to be had.

Let me be clear with my experience with David Letterman as a very young adult. It’s minimal.

I knew David Letterman and Jay Leno as the old white guys with the late night shows that were sparingly funny. Of course, I was too young to have a sophisticated comprehension of humor that didn’t travel beyond gamers frantically raging on YouTube, and my favorite TV game show Wipeout, where contestants went through an impossible obstacle course pinnacled by a row of four balls called, “The Big Balls”.

As far as cultural context is concerned, I know that Letterman is an iconic sacred figure in late-night television and in the comedy world. That doesn’t really mean I know anything about him.

By the end of Letterman’s talk with Obama, I got the sense that I keyed in on a motivating factor for Letterman’s Netflix show, My Next Guest Needs No Introduction.

Letterman is an older gentleman contemplating his full life, and he is searching for his grasp of self through his spectacular guest lineup that has had an impact in the world that we can only dream about but never truly understand. Following Obama are George Clooney, Jay-Z, and Malala Yousafzai. These are people who can be recognized by just one name.

But more important than simply being recognizable is the fact these are humans who have made a significant impact on the world, an impact on our culture. If my prediction is correct, I believe these conversations David has recorded, are tapping into the elusive sense of self that is washed away by the media world.

Which brings me back to Barack Obama, who as President, can easily be seen as a polarizing figure with the half our country showing love and half our country showing irate disgust. I absolutely loathe those who see Obama in only that scope.

The second most impactful statement Obama made during the conversation was a show of his humility. Those who are dignified enough to show boundless amounts of humility deserve a lot of love.

Obama said he doesn’t want to come off as self-important.

I know that statement can easily fall on deaf ears, but you’re kidding yourself if you don’t believe that’s a genuine assessment of his character. Obama has always been one to search for humor in the appropriate moment and has his moments in the Letterman chat. There are two indicators as to why Barack Obama doesn’t have an incredulous ego.

Obama always gives credence and credit to his wife, and he is no stranger to self-deprecating humor.

There’s one last fascinating aspect of the Letterman-Obama interaction. Letterman and Obama shared stories about their children.

When parents talk candidly about their kids, it’s about as humanizing as someone can be. As a young adult, I never fail to be amazed when I see how jazzed up parents are when talking about their kids. I tend to think it’s where a person will be their most honest. There’s nothing closer to home than talking about your family.

Obama spoke on sending his daughter Malia off to college in a hilarious and heartwarming anecdote.

Despite all the jovial talk, underlying the Obama legacy, even beyond the question of what was next, David Letterman ended the conversation with self-reflection.

Now I’ve been consistently referring to Letterman’s show as a conversation, deliberately of course, but the style of the show was an interview. Letterman asked most of the questions, Obama provided his answers. But this interview was deeper than questions and answers. This was a production after all.

Letterman was providing a conversation with a specific purpose. It was clear when John Lewis entered into the fold.

I’ve had the privilege of meeting John Lewis. My interaction didn’t extend beyond ten minutes, but I’ll remember it forever.

It’s not like Lewis and I had an intimate one-on-one deep dive into the state of race and culture in America. I asked Congressman Lewis two questions about his graphic novel he wrote that I read prior to the interview. The impact of Lewis is more than simply his words, it’s his presence. His constant demeanor. Lewis was a friend of Martin Luther King Jr., and if Lewis’ composure was any indication, one can only dream of the disposition and presence that Dr. King had.

John Lewis was never more than a blip in primary school study. If he was in the history textbook, my teachers never mentioned him with any regard. Lewis told me at the time that civil rights education is a 9-word problem.

“Martin Luther King, Rosa Parks, I Have a Dream.”

Lewis’ prominence has risen recently after being attacked by Donald Trump on Twitter and being a major character in the movie Selma.

Letterman cuts away in the middle of his talk with Obama to a recorded conversation with him and Congressman Lewis walking across the Edmund Pettus Bridge, the very same bridge Lewis walks across every year, the same bridge he was left beaten to die on.

What makes Lewis one of the most captivating people of our time is not his gait or manner of speaking. Lewis doesn’t speak prophetically or as a poet would. Lewis rather speaks matter-of-factly. I’ve been witness to how energized and full of vigor Lewis can preach with during a rally, but that’s the political performance. Similar to Obama, Lewis is as approachable as any amiable acquaintance can be.

Letterman cuts to and fro his conversation with Lewis and Obama as he offers a few questions about Lewis to Obama. Obama speaks of Lewis as anyone would speak about a heroic figure, with the utmost respect and dignity.

As the conversation came to its close, Letterman returned to his fixation. Letterman, in the twilight of his television career, was speaking to two of the most prominent figures in recent American history. Letterman is self-aware, so are we as viewers. What is the purpose of this conversation?

With a world overflowing with content where words are exchanged amongst faces and names. We see this occur on late night shows, cable news, podcasts, to TV shows and movies. We live in a world of YouTube, Facebook, and Twitter. Words upon words upon words enter into disjointed conversations that are ubiquitous amongst our cultural discourse. We do a lot of listening, reading, speaking, and thinking. What is it all for?

David Letterman, in one last emotional burst of energy, admits to being on a cruise getting wasted in the Bahamas, meanwhile only a month prior, John Lewis was marching on the Edmund Pettus Bridge in Selma, Alabama, fighting for the culture and future of his people.

“Why wasn’t I in Alabama?” Letterman questions.

What if he had known the cultural significance of what John Lewis was going to create when he marched onto that bridge. Surely if Letterman had known he would be there marching with him. But he wasn’t.

“Why wasn’t I aware?”

I firmly believe that Barack Obama will be remembered fondly as one of the most influential men in American history.

The history books and future articles will focus on the wrong narrative. Future pieces about Obama will focus on him being African American, and him being the President of the most powerful nation on the planet. Sure, his heritage is an important consideration for a bevy of reasons. Being the President is a pretty big deal too. If I was to take a guess, I think Barack would most likely want to be remembered as a great father and husband.

But what his legacy will truly impact is how he added to the culture of America. I predict his best years are ahead of him. Barack Obama’s legacy will be dignity, grace, and enduring positivity.

Maybe David Letterman is searching for the same thing.

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