“I hate It’s A Wonderful Life. I mean, are you kidding me? It’s A Wonderful Life. Didn’t look so wonderful to me. More like It’s A Pathetic Life. George Bailey was a loser, super low energy guy. I immediately sensed he was not much of anything. Horrible businessman with no negotiation skills who couldn’t close a deal if his life depended on it. And when he told that woman he liked that he was going to lasso the moon for her?

I almost puked. Jesus, buy her something nice, you schmuck. And trust me, I’ve been with a lot of women, A LOT, and buying them nice, LUXURY items is the way you get quality women.

He’s lucky she didn’t laugh in his face, but let’s be honest here, she was pretty plain so maybe she didn’t think she could do any better. Look, If I was George Bailey, which I could never be, I would have jumped off the bridge, too.”

“Oh yeah, I like lots of Christmas movies, too. Trading Places, you heard of that? Classic. It’s not really very sophisticated when it comes to business, but it’s great to see luxury and the ability to finance a deal finally get some prominence in a Christmas film. Really got the 80’s right. The 80’s let me tell you, was a great era in American history. And let’s not forget a young Jamie Lee Curtis. Wow. What a set.

You wouldn’t expect it because she looked like a boy mixed with a horse, but she really delivered the goods. Sadly, she’s no longer a ten.”

“Die Hard is another favourite. Foreign money and a bunch of loser terrorists think they can come into America and steal our jobs? On Christmas, the peak consumer cycle of the year?? Think again.”

“LOVED How the Grinch Stole Christmas. A lot of liberals and politically correct types think it’s somehow anti-consumerist. Oh, really? It’s actually a classic story of a misunderstood businessman and how trickle down economics and plutocracies function. The Grinch was a very high energy guy who knew how to make a plan and execute it, and through his industry, smarts, guts and hard work, he was able to amass a fortune, maybe not as much as me, but a fortune all the same. Was there a government that came in and stole all of the Grinch’s profits? No, no there was not. And did he give back to the community? Yes, yes he did. The Christmas message? Stay out of the way of exceptional businessmen like me, and good things will happen.”

I grew up in the Age of Letterman, and I have to say that I view his pending retirement as good news. Over the years my encounters with the Late Show have become sporadic and accidental. It wasn’t just the format that seemed dusty, but Letterman himself looked a little bit old, sometimes even disheveled, and his performance recalled a different era, the man having somehow morphed from being the smartest, edgiest guy in the room to a beloved uncle repeating jokes after Christmas dinner. It wasn’t pathetic, just a little bit sad, like noticing somebody you love age and becoming a smaller, more vulnerable version of himself.

Once a revolutionary who brought irony into the mainstream, he now seems lost in time, usurped by all his competitors who have an organic sense and mastery of social media. Of course, when Letterman started, he was the undisputed champion of improvisational videos, bits that would have played brilliantly on the Internet, but the fact that he was both before and of his time, is no matter,

Back then he was a jolt of electricity into very calm and predictable weather and as a teenager I immediately related to him. He had an anarchic, Frat Boy sensibility, and liking him as opposed to another, lamer option, was a defining tribal characteristic. You wanted to wear the Late Night t-shirt the same way you wanted to wear the t-shirt of a super-cool alt band– it meant something about who you were and how you saw the world. Every night, we all gathered in our university residence to watch Late Night before heading off to our parties. It was a cultural drawing point and it sincerely brought us together.

Letterman has had a massive influence on our cultural landscape, his style and intolerance for the pieties and hypocrisies of celebrity culture– even though he lived within it– have pointed the way for so much of the comedic culture we currently revere.  Now in his late 60’s, it is time for him to go, and it’s very bittersweet. He was a giant, one with a unique gravitas and ability to cut through the bullshit, and I will miss him– as I miss the days of my youth–more than I can say.