Letterman, Colbert and the Art of Building a Legacy

Last week Dave Letterman, host of CBS’ “Late Show with Dave Letterman” announced he was retiring and giving up his chair after more than 30 years of entertaining and challenging many.

For a certain generation of comedians, musicians and viewers, Letterman set a template of hosting that few could duplicate but many would openly imitate to varying degrees of success (1). In reading and researching about this “moment”, I learned that Dave Letterman often sensed he hosted for too long but simply continued “just because”, only leaving when the job was no longer fun for him. Yet, as he got on in age, he simply asked great questions, bringing out the best in his guests or forcing them to come to grips with their broken truths (2).

As tributes poured in (I'll have a few as video after the footnotes. Always after the footnotes. If you only watch one, PLEASE watch Keith Olberman's. Then when you watch a farewell service or something of the affect, compare notes.), the obvious question was “Well...who’s gonna replace Dave?” Media pundits had a field day with this, throwing out different names like Neil Patrick Harris, Chelsea Handler, CBS’s 12:30 Late Night host Craig Ferguson or Comedy Central’s Jon Stewart. Jon Stewart had been “knighted” by many to take this spot, while he constantly built up his reputation by raising the standard of hosting and satire on his show “The Daily Show with Jon Stewart (3)”. And he as a host would have made sense. Instead, it was a colleague and friend of Stewarts that was handpicked for the job: Stephen Colbert of Comedy Central’s “The Colbert Report”. Colbert was on The Daily Show before Jon became host and their rapport (4) and after his joining the team their comedic timing was something  to behold. Then in 2005, Stewart approached Colbert about creating a “spin-off” show to extend their show to one hour. Thus the character “Stephen Colbert” was born, The Colbert Report took off and ‘truthiness’ became an actual word (5)

Colbert is a rare talent who is funny, grounded and, in my opinion, fully up to the task. But that’s not why I’m typing away about this blip on the radar screen of pop culture. As I watched this 'transition' take place, I noticed a few important leadership thoughts:

1 - Great leaders set up other leaders to do greater things

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For all the voices that were pushing Stewart toward a certain direction, his own compass kept him steady and got him to push his good friend in that direction. Now, if you have never seen The Daily Show, what they do is amazing but even cooler? The amount of people Jon has MADE on his show: Steve Carrell. Ed Helms. John Oliver. And now Stephen Colbert. I mean this is why people want to be on his show!  The only thing cooler than doing it yourself, is seeing “your man” do it and feeling great about it. Once “your man” gets it, it’s like “we all did”, in some respects…especially if you don’t NEED it for yourself. All of the guys on his team are positioned to do more than him and he is cool with it. He is Hollywood’s Keith Smith (6). So a great question to ask oneself is "Who do you have around you who you're building into?"

2 - Retirement requires reevaluation

Last week, a great leader shared an article on Why Older Pastors Don’t Retire When They Need To and the first reason listed is their identity. For many leaders, all they have known is the role they’ve been in for years. And the thought of not being known as “_____________” is a non-voiced fear. They get replaced and forgotten about…a picture on a wall with a plaque under it to show their years of service. The only way one could leave this type of role is if they have something to live for BEYOND their role.

When Dave announced his retirement, one of the reasons was the desire to be with his young son, Harry. Hanging with his boy made this millionaire say, “Is this worth it anymore?” Obviously, the job isn’t but it reminds me that every change needs to have that moment of “Is this the end of my life?” It also means that the one who is retiring has to be thinking about something more than themselves…

3 - Pay Respect to The Outgoing Leader Before Jumping Into Their Role

The best way to bridge the past into the present is to do more than acknowledge it but to be thankful for it, even the tough parts (7). In one of my post-secondary classes, we learned that unless the job is a wash, go in learning in your first year with slight changes here and there before simply making it your own. The reason for that is to gain the trust of those who’ve ‘inherted’ and honour the one who you’re replacing. This means not caring about your own legacy but carrying on the best parts of their own. And judging by Colbert’s “character”, that won’t be an issue.


1. Imitators include Conan O’Brian, Jon Stewart, Jimmy Kimmel and Jay Leno. In case you didn’t know, Headlines wasn’t his own creation…

2. A few examples: Dave interviewing Paris Hilton post-jail or Joaquin Phoenix after he went crazy. Dave was the old guy who simply didn’t have time for any crap. Actually, the best is when John McCain stood him up to go on Katie Couric. Amazing.

3. Most recently, Stewart made great social commentary on Christians and the film Noah. Classic. There is a reason why his show has won the Emmy for best variety show 10 times since 2003, losing only once to a show he commissioned.

4. Or, to pay homage to Colbert, “rapporrr”…

5. To understand the character of "Stephen Colbert", watch clips of Bill O’Reilly from Fox News and add humour to it. It is something to behold. The question is always this: Is this scene being commented on by “Stephen Colbert” or Stephen Colbert? That mystery makes for amazing television.

6. Pastor Keith Smith was my boss at Agincourt Pentecostal Church in Toronto for 9 years. For ages, he has mentored amazing people who have gone on to do amazing things in churches, business and more all over the world. A few days ago at a funeral for another great man named Rev. Charles Yates, it was amazing for me to reconnect with so many heroes in my eyes, man who each had mentoring through Keith. Now, if it was up to him, we’d all still be at home serving alongside him. BUT he loves his guys and girls more than what we can bring to the table. And so he allows us to leave the nest and experience new challenges while always being a safe ear for us to turn to. I love that guy. He’s pretty rad.

7. This blog is not to wave over Dave's own indiscretions in his private life. His greatness, in the blog post, is based on his job performance...not on his personal choices. That said, to focus all my thoughts on his failures would be a typical shame. But at the same time, unavoidable. Hence this awkward footnote. Argh.


Chris ChaseComment