5 Greatest Late Night Sidekicks

I don’t know why but I have always been obsessed with late night television. I caught the tail end of Johnny Carson’s tenure at The Tonight Show and enjoyed it, even though I didn’t always understand the political and cultural references. I would then sometimes be able to catch Late Night with David Letterman, which I absolutely loved. Chris Elliott became a celebrity seemingly known only to me at the time (this was prior to the internet, of course).

I’ve read every book I can find about the late night talk show wars, watched HBO’s The Late Shift about Letterman’s move to CBS, and continue to watch as much late night as possible. Much like the soothing rhythm of regular season baseball, late night television is a comfort that helps me put our world into context.

An often overlooked, yet critical, ingredient to the late night talk show is the sidekick. I tend to believe that the more fully the sidekick is integrated into the show, the better the show is overall. It’s a special talent, to be comfortable being second banana, never getting the full credit you deserve. Below are samples from the 5 best sidekicks in late night:

5. Zorak (Space Ghost Coast to Coast)

4. Paul Shaffer

3. Geoff the Robot

2. Andy Richter

1. Ed McMahon

Letterman: Interview with Congressional Medal of Honor Recipient Kyle White

David Letterman is often chastised for not preparing well for interviews. I think sometimes that’s right, as he seems far more interested in having a normal conversation with a person that reading suggested questions from a publicist. If the guest is personable and willing to engage, the conversation goes well. If the guest is only willing to discuss their current movie, they’re going to have a bad time.

The claim that Letterman simply can’t, or won’t, prepare for an interview is simply false. In fact, when he has a guest he respects or a guest he feels has something to say, I think he is an extraordinary interviewer.

Case in point: a recent interview with Congressional Medal of Honor recipient and former Army Sgt. Kyle White. First, I’m disappointed this first clip removes several early minutes of the televised broadcast of Letterman putting Sgt. White at ease, asking him about his background, etc.  It was nice to see Letterman not leap into the emotional part of the firefight, but making it clear that White is an actual human being outside of these events.

Notice how Letterman sets up Sgt. White for a successful interview, guiding him through the discussion, making sure he highlights relevant points, and reducing the glare of the spotlight so that it’s really a conversation between just the two of them, with us listening in on it.

It’s amazing how Letterman conducts this entire interview without once referencing his notes. At times, Letterman knows the narrative so well that he circles back to remind Sgt. White of details he had not mentioned. Throughout the interview, it is given the weight and attention required of someone who has earned respect.

After the essential details of the event are relayed to the audience, Letterman again returns the interview to Sgt. White as a person. He inquires about PTSD, the help he received from the army and how he is doing today. Letterman mentions the importance of the GI Bill and indirectly highlights the plight of jobless veterans by giving Sgt. White the opportunity to highlight his new employment as an investment analyst.

This is just a terrific interview in every way. Letterman demonstrates respect for Sgt. White in so many ways, both verbally and non-verbally. It’s an excellent illustration of how to help a veteran tell their story.

A few other things I like about how Letterman demonstrates respect:

  1. Sgt. White was the first guest on the show, not the last.
  2. Letterman doesn’t make a big show of grandstanding and ‘thanking him for his service on behalf of the American people’ or anything like it. He keeps it personal and treats Sgt. White with warmth and sincerity.
  3. Sgt. White is given all the time he needs to tell his story. These clips are over 12 minutes, and there was additional footage televised that is not included here. The interview is never rushed or cut short so that they can move on to something else.
  4. Sgt. White is given the opportunity to highlight important issues like PTSD, health care, education and employment within the context of his personal story.

This is a terrific interview of a true hero by a television legend. I think it’s worthy of viewing and reflection on both accounts.


Watch This: Future Islands

I had never heard of the band Future Islands before. I’m guessing you haven’t either. Odds are, outside of reading this post you never will. They’re not going to be U2 or even The National. They are a band making music because they love it and have something they want to say.

All of which makes me very, very happy they landed an appearance on The Late Show with David Letterman. Not only did this band I’d never heard of make an appearance, they made the most of it. Weeks later, people (like me) are still buzzing about this performance.

It’s hypnotic, exciting, fun and passionate. It’s also a great song. More than anything though, it shows someone just going for it, seizing the moment and not caring if he looks silly or cool. He’s desperate to make you understand what he’s saying. It’s an actual performance in a time when so many are more concerned with looking cool than being passionate.

The other thing I loved about this is Letterman’s enthusiasm. This is a man that does not suffer fools gladly (see his interviews with Paris Hilton, John McCain and Lindsay Lohan, for example). His interviews can be contentious if you’re not bringing anything to the table. Likewise, if you bring something interesting or exciting, Letterman will be sure his affection is communicated to the audience on your behalf. Just listen to his joy at the end of this song:

“I’ll take all of that you’ve got! That was WONDERFUL!” -David Letterman

It’s clear he had a terrific time watching Future Islands. You can bet it won’t be their last time on the show.

Watch the YouTube video above. I’ve seen it about twenty times now; I’m addicted to it. That’s the power of music, of performance. Nice job, Future Islands. You made the most of your moment!

Further Reading: