(I consider this an addendum to my thoughts on the death of the “old” late night television and the departure from late night of my favourite host Craig Ferguson, which I made in December. So read that if you want a full preamble.

For a briefer preamble: In it, I wrote “Yes, historically speaking, David Letterman’s retirement next year is probably more important (than Ferguson’s last show) since he probably is more responsible for the 12:35am aesthetic than he’s comfortable admitting as a man who wanted to desperately be (Johnny) Carson’s spiritual successor instead.” That’s a big part of why David Letterman is important.)

We live in an age where we have a list for everything. However, David Letterman was doing Top Tens before Top Tens became a well-worn cliché. So we (the “we” in this case is “the Internet”) can be forgiven for all blithely throwing up a Top Ten list to commemorate David Letterman’s 4,263rd episode of Late Show, 6,082nd late night program overall (minus guest hosting duties) and final late night gig of all.

So here’s my Top Ten Favourite David Letterman moments. They’re arguably not the best and it’s nowhere near comprehensive because I cut my late night fandom teeth on his Late Night successor. Nonetheless, here they are:

AN HONOURABLE MENTION: You’ll note that none of Dave’s more infamously confrontational interviews are included; my humour scale tends not to respond to the embarrasment factor. But it’s worth mentioning that their value was at their highest when Dave either thought the guest took themselves too seriously or he had little respect for the guest’s “accomplishments.” It’s a peek into Letterman’s insight when Paris Hilton told him she didn’t want to talk about her time in jail and how he responded. People (rightly) pilloring Letterman for his faults could produce just as much humour.

10 – “Did You Bring Any Mace?,” May 14, 2015, The Late Show
In the interest of acknowledging there’s a recency bias, I’ll put this on the list but leave it at ten. Late night TV works great when you have some sort of motley combination of folks: having gravelly-voiced Tom Waits as guest with an American mainstream sweetheart, George Clooney, standing by works for this reason, while it also serves the purposes of watching three entertainment vets have a chuckle. Clooney handcuffed himself to Dave in an earlier segment in a gag designed to express his disappointment with Letterman’s retirement (“You’re not going anywhere!”). To their credit, they saw the gag through to the episode’s end. Watching Clooney’s delayed reaction to Waits’ tire business joke tickles my pun-loving funny bone.

9 – “It Seems to Me Like You’re Changing Your Style a Bit…,” , Late Night, October 2, 1986
The first of three ’86 moments on this list, this features one of Letterman’s most celebrated featured players from his NBC days impersonating Dave’s most frequent NBC guest in a bit that demonstrates Dave’s most frequently celebrated quality: the “anti talk show” approach. Chris Elliott pokes fun at all of Jay Leno’s predictable delivery points but Dave is quick to immediately deconstruct the bit on the spot and somehow only adds to its humour. Elliott would return two weeks later with Leno himself to deliver a great callback punchline to the routine.

8 – “My Favourite Band Playing My Favourite Song…,” February 21, 2000, Late Show
It’s a strange entry for me to put a musical performance on here because a) it’s not Dave doing anything and b) I could really take or leave the Foo Fighters after their first couple of albums (and this was recorded right as their plunge into mediocrity was already in tilt). But anyone that was in high school/college in the late-90s remembers the power-pop-rock perfection that was The Colour and The Shape, and obviously Letterman loved the signature single.

Letterman was #2 (or 3) in the ratings from 1995 on, but there was a gravitas to Dave that made his coming back from heart surgery in 2000 a much bigger deal than if it had been anyone else. What makes this stand out is that the band didn’t just fly back from South America to play it…they played the hell out of it. For all of the times Letterman was (and is) a jerk where his rivals weren’t, those that did feel warm feelings about him were 100% sincere about it and it came through in their performances. I still kind of get a little goosebump when the synth kicks in and Grohl says, like a giddy eight-year old, “Paul Schaffer!”

7 – “You Need a Ride to the Airport?,” September 24, 2008, The Late Show
Right-wingers say Dave went downhill when “he got political” and believe it or not, I actually agree. Not because of any leanings on my behalf, but because I don’t think Dave did partisan humour well (especially given what his successor was doing in the same timeslot on cable). But what Dave did do well, when he was on, was make fun of the general absurdity of the power politics of everyday life (also see #4). Which is why his takedown of John McCain was a return to form.

We’ve probably all been stood up for a false reason at some point in our life (many of us are also probably guilty of same). What’s interesting about this clip is that Dave really gets across over the course of the show how much his initial admiration of McCain informs his disappointment when John bails on him that way. The fact that noted left-wing pundit Keith Olbermann just so happens to be Dave’s substitute for McCain as the Couric interview is unfolding is like an extra layer of delicious wickedness.

6 – “As You Can Tell, Andy Kaufman’s is Here, Sorta…,” July 29, 1982, Late Night
This is a “my favourite” list, not “best,” and since I’m a wrestling fan, I’m biased and this makes the list. Jerry Lawler and Kaufman decided to go “off page,” as it were, in one of the most important moments in pro wrestling history and shockingly enough, a formative moment in Letterman’s career. I think it would have been memorable TV regardless of the host but Dave handled it with a coolhanded flippancy that surpasses how any of his contemporaries would have. Also, his little quip at 14:55 (that doesn’t even draw a huge laugh in and of itself) is maybe my favourite Dave one-liner, giving you a clever reference to late night history to that point…

5 – “How Did You Get This Job, By the Way…?,” February 28, 1994, Late Night
I wish the whole appearance was on the webs right now but it isn’t. But I’m a big Conan O’Brien fan and anyone born before 1985 probably remembers the reaction to him getting the job to succeed Letterman on NBC’s Late Night: “Who the hell is this guy, why’s he so nervous and when is he going to get funny?” But a lot of our generation thought there was potential, and getting Dave’s blessing was an enormous step forward. Given that Letterman’s production company was already planning a rival program, he didn’t have to do that, but typically Dave wasn’t good at hiding things that he hated– or things he liked. (A lesser remembered appearance is here— with another quick Dave’esque zinger at 0:49 and an oddly prescient statement about Conan’s future).

4 – “This is Gonna Be Fun to Work with These People, Isn’t It?…,” April 8, 1986, Late Night
If you want to know why Dave “jumped the shark” in the late 90s or early 2000s, it was most notably because he stopped doing remotes. And this one was hands down the most intentionally and unintentionally genius one that he ever did. When he delivered a fruit basket to the headquarters of new NBC owner General Electric, he all at once poked fun at the general hassles of bureaucracy, at how conglomeration created bosses and owners isolated from their employees, and at his own “bite the hand” mentality that would ultimately cost him The Tonight Show. Not like it was the last time he’d do this. And certainly not the first…

3 – “…and I’m Not Wearing Pants,” August 19, 1985, Late Night/Today Show
#2 is Dave at his “elder statesmen” best. This is Dave at his “voice of the young comic generation” best. (He was my age at the time, so I may be trying to overinterpret 38 as young– wishful thinking?). Anyone that made a point to stay up to watch the “hip” Letterman probably also considered The Today Show as overhyped anathema and Dave capitalized on it all too well. It’s probably also no coincidence in Dave’s mind that just as NBC would repeat itself in his universe with seemingly absurd TV-think, they would be equally redundant handling their morning flagship.

2 – “Don’t Blame Conan,” January 19, 2010, Late Show
Mix Letterman’s blessing of O’Brien as his successor in #5, his proclivity for poking fun at invisible network bosses in #4/#3 and his sourness at losing his dream job to the comedian cited in #9 and…voila! If you can forgive the excessive Paul Schaffer interventions in this desk bit, you’ll recognize it as a pivotal moment in Dave’s status as late night’s elder statesman.

It’s impossible to mention Letterman’s careers without also referencing Jay Leno’s. By all accounts, more people watched Leno and we should like Leno better: a faithful husband with gentle comedy and a kind exterior. Still, there was always something…off…about Jay to those that considered themselves more seasoned comedy fans. You felt like for better or worse, you knew Dave, but you didn’t really know Jay.

Dave works that to his advantage here and again does what he does best: deconstruction. The furor over NBC trying to elbow Jay Leno back into 11:35pm, and Leno’s apparent overwillingness to surrender to the corporate structure that drove Dave crazy, kicked off a glorious (if not also redundant) week of high-level Letterman bitching about Jay and NBC. What makes the bit brillant is that Dave doesn’t focus on Jay’s alleged selfishness, he instead focuses on a seemingly innocuous statement (“don’t blame Conan”), dissects its absurdity and divulges what he sees as the personality flaw that informs that statement. Dave would be the cranky old man before and after this, but this was one of the times he was a particularly astute cranky old man.

1 – “The Arbitration,” June 27, 1986, The Tonight Show
Yes, I’m being ironic by making the number one entry something from the show that got away from Dave…but most times when people praise Letterman, it’s for his anti-humour-humour, his diffusing of normal celebrity sycophantism, general curmudgeonry and his widespread influence.

But this is just straight-up clever and funny Dave: bantering with his late-night idol and delivering a hilarious comedy premise that works on YouTube today, worked on television in the 80s and would have easily worked on radio in the 30s (or the stage in any era). Tonight’s Late Show may mark the end of a run for a TV host that was of his time, but there was certainly a spark there that carried beyond his years.

I’m sure he’ll enjoy his retirement like anyone of his vintage should: with a big, big bottle of alka seltzer.