Tonight is going to be a hard night.  David Letterman is signing off after 33 years in late night television, and I don’t know if I can watch.

I grew up watching Dave.  I had a TV in my room, and instead of sleeping I would watch the offerings that were on after the 10:00 news.  On most nights, I made it as far as Johnny Carson’s first guest.  But there were some nights where I was still awake at 11:30, and I was introduced to the gap-toothed comedian from Indiana who did strange things after Johnny said good night.

Letterman made broadcasting seem fun.  He would take viewers through the hallways of 30 Rock.  As a kid, TV shows seemed like a self-contained world.  Letterman made TV look like a factory.  He seemed to delight in showing you how it all worked at the NBC factory. “Late Night” was in one studio, local news was across the hall, Tom Brokaw anchored “NBC Nightly News” on a different floor, and Dave could heckle “Today” host Bryant Gumbel whenever he wanted.

Then came the palace intrigue of the “late night wars” and I was hooked.  Broadcasting was a business that contained bells, whistles, wires, knobs, and truckloads of high drama.  I loved reading about it and hoped to be a part of it.

I also watched Letterman’s evolution from young voice of the TV generation to elder statesman.  He succeeded by doing TV his way, and that’s a scary proposition.

According to the book “I’m Dying Up Here” by William Knoedelseder, Letterman did something that most other people would consider career suicide.   Five months after his first guest appearance as a stand-up comic on “Tonight” in November 1978, he was asked for fill in for Carson.  Letterman’s first time hosting “Tonight” was in April 1979.  It was Oscar Night, and Carson was hosting the Academy Awards.  It also happened to be in the middle of the “strike” of comedians at the Comedy Store.  They wanted to get paid for their appearances at the club.

After the show, Letterman told Carson’s producer Fred de Cordova that he could not attend the post-show meeting because he had to drive back to the Comedy Store to walk the picket line.  A typical comedian would have blown off his fellow comics.  After all, when you’re guest-hosting for Carson, you’ve made it.  He stuck by his fellow comics.  It was an incredibly gutsy move.

That sense of fearlessness made him a very wealthy man.  “Late Night” inspired a generation of comedians, writers, and performers.  The group that came of age in the 80’s and 90’s became fluent in the language of irony, thanks to Letterman.

But that sense of fearlessness would also doom him to also-ran status in the war against Jay Leno.  Letterman followed his gut.  Leno was a Humor Mechanic.  He would obsessively pore over his jokes.  The setup, the delivery, the audience reaction.  By the time he hosted “Tonight” in the 1990’s, he would devour network research and ratings with the same zeal.  Letterman’s humor was aimed at people who were hip enough or smart enough to get the joke.  Leno recalibrated his humor for everyone else.

Leno’s approach worked, and by 1995 he was the lead dog in late night.  After five years of what could generously be described as “panic mode,” Letterman resigned himself to the fact that he would be a comfortable number two.  When he achieved peace with that fact, he altered his act again.  Instead of trying to create water cooler moments, he made the show about whatever was rattling around his head.  Instead of prepared comedy bits, he would talk to the viewer from behind the desk.  The monologue owed more to talk radio than talk television, but it was funnier than anything the writers could have concocted.

When Leno signed off for good in 2014, Letterman had the good sense to be himself.  He could have tried to compete with Jimmy Kimmel and Jimmy Fallon in creating viral videos or re-orienting his show to appeal to the social media generation.  Had he gone down that road, he would have looked silly.  Instead, Letterman realized he will never be “a Jimmy” and retired.

There’s something to be said for challenging yourself.  However, in media, the worst mistake someone can make is trying to be something they are not.  When I was first starting out in talk radio, the surefire path to success was to be an angry man.  You had to be ready to launch into a spittle-flecked monologue about anything in the news.

Since I wanted to work in talk radio, I tried to adopt the angry man posture.  It felt horrible, it sounded worse, and I came out of the experience realizing that if something makes be uncomfortable, that feeling is probably correct.  The lesson:  I’m very bad at playing a jerk on the radio.

Go with your gut.  Walk the picket line with your fellow comics.  Shoot tennis balls at the “Live at Five” studio door, and don’t attempt viral videos if you know they will be bad.

Enjoy retirement Dave.  Thanks for teaching this broadcaster to be himself.